Jay-Z can be briefly heard on several of Jaz-O's early recordings in the late 1980s and early 1990s, including "H. P. Gets Busy", "The Originators" and "Hawaiian Sophie". Jaz-O's record label came up with the idea to create an album with a concept reminiscent of DJ Jazzy Jeff & the Fresh Prince, featuring Jaz-O as the rapper, Jay-Z as the hype man, and Irv Gotti as the DJ. While working on the album Word to the Jaz in London in 1988, Jay-Z and Gotti began to build their relationship on the trip. Jay-Z became embroiled in several battles with rapper LL Cool J in the early 1990s. He first became known to a wide audience on the posse cut "Show and Prove" on the 1994 Big Daddy Kane album Daddy's Home. Jay-Z has been referred to as Big Daddy Kane's hype man during this period, although Kane explains that he did not fill the traditional hype man role, and was instead basically making cameo appearances on stage. "When I would leave the stage to go change outfits, I would bring out Jay-Z and Positive K and let them freestyle until I came back to the stage."

According to his second verse on "99 Problems", released in 2003, Jay-Z was allegedly stopped by an NYPD detective in 1994 while en route to I-95, possibly for a search of drugs in his car. Detection dogs were called, but another police car had passed; Jay-Z was let go soon after. Jay-Z appeared on a popular song by Big L, "Da Graveyard", and on Mic Geronimo's "Time to Build", which also featured early appearances by his former Murder Inc. colleagues Ja Rule and DMX in 1995. His first official rap single was "In My Lifetime", which was released with an accompanying music video in 1995. An unreleased music video was also produced for the B-side "I Can't Get with That".

With no major label to give him a record deal, Jay-Z sold burned CDs out of his car, and with Damon "Dame" Dash and Kareem "Biggs" Burke, created Roc-A-Fella Records as an independent label in 1995. After striking a distribution deal with Priority, Jay-Z released his 1996 debut album Reasonable Doubt with beats from acclaimed producers such as DJ Premier and Super DJ Clark Kent and an appearance by The Notorious B.I.G. The album reached number 23 on the Billboard 200 and went gold that year. After reaching a new label distribution deal with Def Jam in 1997, Jay-Z released his follow-up In My Lifetime, Vol. 1. Featuring production by Sean Combs, DJ Premier, and Ski, it earned platinum status in the United States.

In 1998, Jay-Z released Vol. 2... Hard Knock Life which spawned the biggest hit of his career at the time, "Hard Knock Life (Ghetto Anthem)". He relied more on flow and wordplay, and he continued with his penchant for mining beats from the popular producers of the day such as Swizz Beatz, an upstart in-house producer for Ruff Ryders, and Timbaland. Other producers included DJ Premier, Erick Sermon, The 45 King, and Kid Capri. Charting hits from this album included "Can I Get A...", featuring Ja Rule and Amil, and "Nigga What, Nigga Who", featuring Amil and Jaz-O. Vol. 2 would eventually become Jay-Z's most commercially successful album; it was certified 5× Platinum in the United States and has to date sold over five million copies. The album went on to win a Grammy Award, although Jay-Z boycotted the ceremony protesting DMX's failure to garner a Grammy nomination and the academy's decision to not broadcast urban music categories. In 1999, Jay-Z collaborated with Mariah Carey on "Heartbreaker", a song from her seventh album, Rainbow. The song became Jay-Z's first chart-topper in the U.S., spending two weeks atop the Billboard Hot 100. In that same year, Jay-Z released Vol. 3... Life and Times of S. Carter. The album proved successful and sold over 3 million copies. Vol. 3's most successful single was "Big Pimpin'", featuring UGK.

In 2000, Jay-Z released The Dynasty: Roc La Familia, which was originally intended to become a compilation album for Roc-A-Fella artists but Def Jam turned into a Jay-Z album. The album helped to introduce newcomer producers The Neptunes, Just Blaze, Kanye West, and Bink, which have all gone on to achieve notable success. This is also the first album where Jay-Z utilizes a more soulful sound than his previous albums. The Dynasty sold over two million units in the U.S. alone.

In 2001, Jay-Z spoke out against Prodigy after he took an issue with Jay-Z's "Money, Cash, Hoes." Prodigy felt that the lyrics alluded disparagingly to his shared dispute with Mobb Deep against Tupac Shakur, Snoop Dogg, and Death Row Records. He later performed the song "Takeover", at Summer Jam 2001, a diss-track about Nas, Prodigy, and Mobb Deep. At the same concert, Jay-Z brought Michael Jackson up on stage with him. A line at the end of "Takeover" referred to Nas, who criticized him on "We Will Survive". Nas responded with a diss of his own, and Jay-Z straightaway added a verse to "Takeover" which dissed Nas and would start a feud between the two rappers. The feud had ended by 2005; Jay-Z stated that record producer Mark Pitts had helped them settle their differences.

On September 11, 2001, Jay-Z released his sixth studio album, The Blueprint, which received a five-mic review from hip-hop magazine The Source. Written in just two days, the album sold more than 427,000 copies, debuted at number one on the Billboard 200 and reached double platinum certification by the Recording Industry Association of America. Eminem guest performed and produced its song, "Renegade". Four tracks were produced by Kanye West. The Blueprint includes the songs "Izzo (H.O.V.A.)", "Girls, Girls, Girls", "Jigga That Nigga", and "Song Cry". As of February 2012, the album had sold 2.7 million copies worldwide. In 2019, The Blueprint was selected by the Library of Congress for preservation in the National Recording Registry for being "culturally, historically, or aesthetically significant".

In October 2001, Jay-Z pleaded guilty to aggravated assault for stabbing record producer Lance Rivera at the Kit Kat Klub in New York City in 1999. Despite Jay-Z's sentence of three years probation for the crime, Rivera later recanted the allegations in 2023.

Jay-Z then collaborated with Chicago singer R. Kelly to release collaborative studio album, The Best of Both Worlds in March 2002. In November of that year, Jay-Z released his seventh studio album The Blueprint2: The Gift & The Curse—a double album. The album debuted on the Billboard 200 at number one, selling over 3 million units solely in the U.S. and surpassing The Blueprint. It yielded a single-disc re-issue, The Blueprint 2.1, which retained half of the songs from the original. Its original release spawned two hit singles, "Excuse Me Miss" and "'03 Bonnie & Clyde", which features Jay-Z's then-girlfriend, Beyoncé, and contained the track "A Dream", featuring Faith Evans and the late Notorious B.I.G.; the re-issue spawned the single "La-La-La", which was a sequel to "Excuse Me Miss" and failed to match its commercial success.

After visiting the south of France, Jay-Z announced work on his eighth studio album, The Black Album at the opening of the 40/40 Club. He worked with several producers including Just Blaze, The Neptunes, Kanye West, Timbaland, Eminem, DJ Quik, 9th Wonder, The Buchanans, and Rick Rubin. Notable songs on the album included "What More Can I Say", "Dirt off Your Shoulder", "Change Clothes", and "99 Problems". The Black Album has sold over 3 million copies in the U.S.

On November 25, 2003, Jay-Z held a concert—billed as a "retirement party" at Madison Square Garden in New York City, which was later the focus of his 2004 documentary, Fade to Black. All proceeds went to charity. Other performers included collaborators the Roots (in the form of his backing band), Missy Elliott, Memphis Bleek, Beanie Siegel, Freeway, Mary J. Blige, Beyoncé, Twista, Ghostface Killah, Foxy Brown, Pharrell Williams and R. Kelly, with appearances by Voletta Wallace and Afeni Shakur, the mothers of the Notorious B.I.G. and Tupac Shakur, respectively. While Jay-Z had attested to a retirement from making new studio albums, various side projects and appearances soon followed. Included in these were a greatest hits record, as well as the release and tour of Unfinished Business, the second collaborative album between Jay-Z and R. Kelly.

In 2004, Jay-Z collaborated with rock group Linkin Park, in which they released their collaborative remix EP Collision Course, which featured mashups of both artists' songs, as well as a concert DVD. The album's only single, "Numb/Encore", went on to win a Grammy Award for Best Rap/Sung Collaboration, and was performed with Linkin Park live at the Grammys, with a special appearance by Paul McCartney, who added verses from the song "Yesterday". The EP sold over 1 million copies in the U.S. Jay-Z was the executive producer of The Rising Tied, the debut album of Fort Minor, the hip hop side project of Linkin Park rapper Mike Shinoda. Jay-Z also planned to retire in 2004.

Later in 2004, Jay-Z was named president of Def Jam Records, which led to Jay-Z, Dash and Biggs selling their remaining interests in Roc-A-Fella Records and Jay-Z taking control of both of the companies. This major industry move was reportedly prompted by disagreements between Jay-Z and Dash as to what direction Roc-A-Fella could undertake.

On October 27, 2005, Jay-Z headlined New York's Power 105.1 annual concert, Powerhouse. The concert's title, "I Declare War," led to intense speculation in the preceding weeks on whom exactly Jay-Z would declare war. As he had previously "declared war" on other artists taking lyrical shots at him at other events, many believed that the concert's title represented an all-out assault by Jay-Z upon his rivals. The theme of the concert was Jay-Z's position as president and CEO of Def Jam, complete with an on-stage mock-up of the Oval Office. Many artists made appearances such as the old roster of Roc-A-Fella records artists, as well as Ne-Yo, Teairra Marí, T.I., Young Jeezy, Akon, Kanye West, Paul Wall, the LOX, and Sean Combs.

At the conclusion of the concert, Jay-Z put many arguments to rest to the surprise of hip hop fans. The most significant development in this show was closure to the infamous hip hop rivalry between Jay-Z and Nas. The two former rivals shook hands and shared the stage together to perform Jay-Z's "Dead Presidents" blended with Nas's song "The World is Yours".

Jay-Z returned with his comeback album on November 21, 2006, titled Kingdom Come. Jay-Z's comeback single, "Show Me What You Got", was leaked on the Internet in early October 2006. The album, which was scheduled for release later on that month, received heavy air-play after its leak, causing the FBI to step in and investigate. Jay-Z worked with video director Hype Williams, and the single's video was directed by F. Gary Gray. The album features production from Just Blaze, Pharrell, Kanye West, Dr. Dre and Coldplay's Chris Martin (single entitled "Beach Chair"). The first week saw 680,000 sales of the CD, enough to be his "biggest sales week ever" as Billboard reported. This album has sold 2 million copies in the U.S. and is certified double platinum.

Jay-Z released his tenth album entitled American Gangster on November 6, 2007. After viewing the Ridley Scott film of the same name, Jay-Z was heavily inspired to create a new "concept" album that depicts his experiences as a street-hustler. The album is not the film's official soundtrack, although it was distributed by Def Jam. Jay-Z's American Gangster depicts his life in correlation to the movie American Gangster. At the start of the album's first single, "Blue Magic", Jay-Z offers a dealer's manifesto while making references to political figures of the late 1980s with the lyric: "Blame Reagan for making me to into a monster, blame Oliver North and Iran-Contra, I ran contraband that they sponsored, before this rhymin' stuff we was in concert." Also notable about the "Blue Magic" music video was Jay-Z flashing €500 notes; Harvard Business School professor Rawi Abdelal called this a "turning point in American pop culture's response to globalization." The album has sold 1 million copies in the U.S. On January 1, 2008, Jay-Z resigned as president of Def Jam.

In winter 2008, it was announced that Jay-Z would become the first major hip hop artist to headline Britain's Glastonbury Festival. Tickets sold out quickly. Former headliner Noel Gallagher of Oasis condemned the festival organizers for choosing Jay-Z to headline a traditionally guitar-driven festival. "I'm sorry, but Jay-Z?" Gallagher asked, swearing. "No chance. Glastonbury has a tradition of, kind of, guitar music, do you know what I mean? And even when they throw the odd curve balls in on a Sunday night—you go, 'Kylie Minogue? I don't know about that', do you know what I mean?—but I'm not having hip hop at Glastonbury, no way, no, no. It's wrong." As controversy mounted, Jay-Z replied, "We don't play guitars, Noel, but hip hop has put in its work like any other form of music. This headline show is just a natural progression. Rap music is still evolving. We have to respect each other's genre of music and move forward." Jay-Z opened his Glastonbury set with a tongue-in-cheek cover of Oasis's iconic song "Wonderwall", and went on to deliver a performance heralded as a successful response to pre-festival criticism. The guitar used in this performance was later shown at the Book of HOV exhibit in the Brooklyn Library.

He also headlined many other summer festivals in 2008, including Roskilde Festival in Denmark, Hove Festival in Norway and O2 Wireless Festival in London. During Kanye West's concert of August 6, 2008, at Madison Square Garden, Jay-Z came out to perform a new song and he and West proclaimed that it was to be on The Blueprint 3. On May 21, 2009, Jay-Z announced he would be parting ways with Def Jam, and had struck a multi-million-dollar deal to sign with Live Nation, with whom he would start his Roc Nation imprint which would serve as a record label, talent/management agency, and music publishing company and also partnered with production team Stargate to start a record label called StarRoc. Jay-Z's 11th studio album The Blueprint 3 was originally to be released on September 11, 2009, but was instead released in North America on September 8, 2009, due to increasing anticipation. Its international release followed on September 14. It is his 11th album to reach No. 1 on the Billboard 200 and surpassed Elvis Presley's previous record. On October 9, 2009, Jay-Z kicked off his tour for The Blueprint 3, during which he supported his new album in North America. In a Shave Magazine review of his performance at Rexall Place in Edmonton, Jake Tomlinson expressed that "It was the type of smooth performance you would expect from the hip-hop superstar." The review gave this performance 4 stars. His North American tour continued until November 22, 2009. At his concert on November 8, 2009, at UCLA's Pauley Pavilion, Rihanna joined him on stage and performed "Hard" for the first time, then performed "Run This Town" with Jay-Z. Among his success, Jay-Z has ventured into producing Broadway shows. Along with Jada Pinkett Smith and Will Smith, Jay-Z helped produce the play Fela!, a musical celebrating the work of the late Nigerian star Fela Kuti. Jay-Z said he was inspired by the power of Kuti's work and his life story, which resulted in his interest to help produce the musical. Fela! is a story about an African pioneer and political activist who made his first moves on the scene during the 1970s.

On January 23, 2010, Jay-Z released a track, "Stranded (Haiti Mon Amour)", with Rihanna, and U2's Bono and The Edge, and performed it at the Hope For Haiti Now telethon. In June 2010, Eminem and Jay-Z announced they would perform together in a pair of concerts in Detroit and New York. The event was dubbed The Home & Home Tour. The first two concerts rapidly sold out, prompting the scheduling of an additional show at each venue. Jay-Z was the supporting act for U2 on the Australian and New Zealand leg of their U2 360° Tour, beginning in Auckland, New Zealand, in November 2010, followed by Melbourne, Sydney, Brisbane and Perth in December.

Jay-Z would later appear with Kanye West on Watch the Throne, a full-length LP with origins as a five-track EP. Recording sessions for the album took place at various recording locations and began in November 2010. The first single released for the project was "H•A•M". The track was co-produced by Lex Luger and West himself. The track ended up being on the deluxe edition of the album. The follow-up to that was the second single "Otis", which premiered on Funkmaster Flex's Hot 97 radio show, and was later released to the iTunes Store eleven days later. The song's existence, along with several other tracks from the album, was confirmed during a listening session hosted by Jay-Z. The album was first released on the iTunes Store, five days prior to its being released in physical format, a strategy Jay-Z later said was used to block an internet leak. It debuted at No. 1 on the iTunes Store in 23 countries. It also broke Coldplay's record for most albums sold in one week on the online retailer, selling 290,000 copies on iTunes alone. It held that record until Lil Wayne's Tha Carter IV was released twenty-one days later, selling 10,000 copies more. It debuted on the U.S. Billboard 200 chart at No. 1, selling 436,000 copies in its first week. The album received generally positive reviews. Jay-Z and West later gave a surprise performance of "Otis" at the 2011 MTV Video Music Awards.

In May 2012, Jay-Z and former Philadelphia mayor Michael A. Nutter announced Jay-Z as the curator and the headliner for the first annual "Budweiser Made in America" festival at Fairmount Park in Philadelphia on September 1 and 2, 2012. The performance was produced by Live Nation and assembled an eclectic lineup of "rock, hip hop, R&B, Latin music and dance" musicians. Jay-Z and Rihanna were the two main headlining acts for BBC Radio 1's 2012 Hackney Weekend music festival on June 23 to 24. Jay-Z opened his set with an appearance from Rihanna, they performed "Run this Town". On September 6, "Clique" was released, a single from the album "Cruel Summer", by GOOD Music. Kanye West and Big Sean starred alongside Jay-Z on the track. Jay-Z took the subway to his sold-out show at The Barclays Center on October 6, 2012. In December 2012, Coldplay performed with Jay-Z at the Barclays Center in Brooklyn.

On September 23, 2010, Q-Tip confirmed working on Jay-Z's follow-up album to The Blueprint 3, saying the album was to hit stores by spring 2011. In May 2012 it was reported that Jay-Z would work on new music with Roc Nation producer Jahlil Beats. Beats told XXL magazine: "Me and Jay-Z been going back and forth. He picked a couple of my joints that he's working on. I don't even wanna say too much about Jay, but we definitely working on some stuff. I haven't even sent him a bunch of beats. I sent him my favorite stuff. He hit me right back like, 'Yo, I'ma go in on this,' or, 'I like this.'" The album was named one of the most anticipated albums of 2013 by Complex Magazine, MTV, and XXL. The album was produced by Jahlil Beats, Kanye West, Rick Rubin, Swizz Beatz, Timbaland, and Pharrell Williams. Jay-Z also co-produced and performed on Justin Timberlake's comeback single "Suit & Tie" from his third studio album The 20/20 Experience, the song itself was produced by both Jay-Z and Timberlake's mutual friend, Timbaland. In July 2013, Timberlake and Jay-Z embarked on the co-headlining Legends of the Summer Stadium Tour.

During the fifth game of the 2013 NBA Finals, Carter announced his twelfth studio album, Magna Carta Holy Grail, and was released on July 4, 2013. Not long after, Jay-Z confirmed that the hyphen in his stage name would be left out and officially stylized in all capital letters. Magna Carta Holy Grail debuted at number one on the Billboard 200 and sold 528,000 copies in its first week, which bypassed its predicted debut in the range of 350,000 to 400,000. In December 2013, it was announced that Jay-Z had received nine nominations at the 2014 Grammy Awards, more than any other artist. Jay-Z appeared on his wife Beyoncé's self-titled fifth studio album, Beyoncé, with a feature on the song "Drunk in Love". They performed this song together at the 56th Annual Grammy Awards opening. The song and its accompanying album would later win three Grammy Awards including Best R&B Performance at the 2015 ceremony. In 2016, he won a lawsuit for the song "Made in America" with Kanye West featuring Frank Ocean against Joel McDonald.

In early June 2017, posters were displayed in New York City and Los Angeles, and banner ads were placed on the Internet promoting a Tidal-related project titled 4:44. A teaser ad was aired during the NBA Finals on June 7 featuring actors Mahershala Ali, Lupita Nyong'o and Danny Glover in a one-minute video, ending in "4:44 – 6.30.17, Exclusively on Tidal". On June 18, the project was confirmed to be a new Jay-Z album, and a clip featuring a song titled "Adnis" was posted on Sprint's YouTube page. 4:44 was released through Roc Nation and Universal Music Group, as an exclusive to Sprint and Tidal customers. The album is the first in a planned series of music exclusives from the Sprint–Tidal partnership. For a short time, on July 2, the album was made available for free digital download in Tidal's site. A physical edition was released on July 7, including three additional tracks. On the same day, the album was made available to other streaming platforms, such as Apple Music, Google Play Music and Amazon Music.

The album received widespread acclaim from critics, who praised its emotional and personal content. On July 5, the album was certified Platinum by the Recording Industry Association of America (RIAA), in recognition of one million copies purchased by Sprint and offered to consumers as free downloads. It debuted at number one on the U.S. Billboard 200, making it Jay-Z's 13th consecutive studio album to top the chart. The album spawned two singles, the title track "4:44" and "Bam", as well as several music videos, directed by a variety of high-profile collaborators. The album received a Grammy Award nomination for Album of the Year, while the title track was nominated for Song of the Year and "The Story of O.J." was nominated for Record of the Year at the 60th Annual Grammy Awards. Two years later, he became hip-hop's first artist to achieve billionaire status.

On June 6, 2018, Jay-Z and Beyoncé kicked-off the On the Run II Tour in Cardiff, United Kingdom. Ten days later, at their final London performance, the pair unveiled Everything Is Love, their much-awaited joint studio album, credited under the name The Carters. The pair also released the video for the album's lead single, "Apeshit", on Beyoncé's official YouTube channel. The song won two awards from eight nominations at the 2018 MTV Video Music Awards.

In 2021, Jay-Z was inducted into the Rock and Roll Hall of Fame along with fellow rapper LL Cool J. He also appeared on the song "Jail" on Kanye West's 2021 album Donda, which went on to win Grammy Award for Best Rap Song at the 64th Annual Grammy Awards and on the song "Love All" from Drake's 2021 album Certified Lover Boy. In 2022, his first feature was a collaboration with fellow rapper Pusha T, "Neck & Wrist" featuring Pharrell Williams from Pusha T's album, It's Almost Dry. His feature was succeeded by a four-minute guest appearance on DJ Khaled's album title track, "God Did". He also was awarded the Primetime Emmy Award for Outstanding Variety Special (Live), as a producer for the Super Bowl LVI halftime show. In 2023, Billboard and Vibe published a list of the 50 greatest rappers of all time, where they claimed Jay-Z is the greatest rapper of all time. The list was met with widespread backlash. That same year, the Brooklyn Library featured the Book of HOV exhibit. The showcase included artifacts commemorating Jay-Z's career. The next year, the exhibit was turned into a book, The Book of HOV: A Tribute to Jay-Z. Similar to the exhibit, the physical book recounted Jay-Z's life and career, including images, interviews, and professional insights.

In 2026, Jay-Z released "Dead Presidents" on streaming services and a limited-edition vinyl, CD and cassette tape version on his website, to celebrate the 30th anniversary of his debut studio album Reasonable Doubt. He also added the umlaut to his stage name, which was a callback to the artwork of the album. In 2026, The New York Times named Jay-Z one of the "30 Greatest Living American Songwriters."

In March 2026, Jay-Z announced a three shows at Yankee Stadium scheduled for July 2026 to commemorate the 25th and 30th anniversaries of his albums The Blueprint and Reasonable Doubt. In May 2026, Jay-Z headlined the Roots Picnic festival, marking his first headlining set in six years. In June 2026, Jay-Z and Roc Nation announced the Jay-Z 30 Tour concert series, with shows scheduled in Paris in September and Los Angeles in October to commemorate the 30th anniversary of his debut album Reasonable Doubt.

Jay-Z says his earliest exposure to music was through his parents' record collection, which was mostly of soul artists such as Marvin Gaye and Donny Hathaway. He says "I grew up around music, listening to all types of people... I'm into music that has soul in it, whether it be rap, R&B, pop music, whatever. As long as I can feel their soul through the wax, that's what I really listen to." He often uses excerpts from these artists as samples in his work, particularly in the Kanye West productions included on The Blueprint.

Jay-Z can be briefly heard on several of Jaz-O's early recordings in the late 1980s and early 1990s, including "H. P. Gets Busy", "The Originators" and "Hawaiian Sophie". Jaz-O's record label came up with the idea to create an album with a concept reminiscent of DJ Jazzy Jeff & the Fresh Prince, featuring Jaz-O as the rapper, Jay-Z as the hype man, and Irv Gotti as the DJ. While working on the album Word to the Jaz in London in 1988, Jay-Z and Gotti began to build their relationship on the trip. Jay-Z became embroiled in several battles with rapper LL Cool J in the early 1990s. He first became known to a wide audience on the posse cut "Show and Prove" on the 1994 Big Daddy Kane album Daddy's Home. Jay-Z has been referred to as Big Daddy Kane's hype man during this period, although Kane explains that he did not fill the traditional hype man role, and was instead basically making cameo appearances on stage. "When I would leave the stage to go change outfits, I would bring out Jay-Z and Positive K and let them freestyle until I came back to the stage."

According to his second verse on "99 Problems", released in 2003, Jay-Z was allegedly stopped by an NYPD detective in 1994 while en route to I-95, possibly for a search of drugs in his car. Detection dogs were called, but another police car had passed; Jay-Z was let go soon after. Jay-Z appeared on a popular song by Big L, "Da Graveyard", and on Mic Geronimo's "Time to Build", which also featured early appearances by his former Murder Inc. colleagues Ja Rule and DMX in 1995. His first official rap single was "In My Lifetime", which was released with an accompanying music video in 1995. An unreleased music video was also produced for the B-side "I Can't Get with That".

With no major label to give him a record deal, Jay-Z sold burned CDs out of his car, and with Damon "Dame" Dash and Kareem "Biggs" Burke, created Roc-A-Fella Records as an independent label in 1995. After striking a distribution deal with Priority, Jay-Z released his 1996 debut album Reasonable Doubt with beats from acclaimed producers such as DJ Premier and Super DJ Clark Kent and an appearance by The Notorious B.I.G. The album reached number 23 on the Billboard 200 and went gold that year. After reaching a new label distribution deal with Def Jam in 1997, Jay-Z released his follow-up In My Lifetime, Vol. 1. Featuring production by Sean Combs, DJ Premier, and Ski, it earned platinum status in the United States.

In 1998, Jay-Z released Vol. 2... Hard Knock Life which spawned the biggest hit of his career at the time, "Hard Knock Life (Ghetto Anthem)". He relied more on flow and wordplay, and he continued with his penchant for mining beats from the popular producers of the day such as Swizz Beatz, an upstart in-house producer for Ruff Ryders, and Timbaland. Other producers included DJ Premier, Erick Sermon, The 45 King, and Kid Capri. Charting hits from this album included "Can I Get A...", featuring Ja Rule and Amil, and "Nigga What, Nigga Who", featuring Amil and Jaz-O. Vol. 2 would eventually become Jay-Z's most commercially successful album; it was certified 5× Platinum in the United States and has to date sold over five million copies. The album went on to win a Grammy Award, although Jay-Z boycotted the ceremony protesting DMX's failure to garner a Grammy nomination and the academy's decision to not broadcast urban music categories. In 1999, Jay-Z collaborated with Mariah Carey on "Heartbreaker", a song from her seventh album, Rainbow. The song became Jay-Z's first chart-topper in the U.S., spending two weeks atop the Billboard Hot 100. In that same year, Jay-Z released Vol. 3... Life and Times of S. Carter. The album proved successful and sold over 3 million copies. Vol. 3's most successful single was "Big Pimpin'", featuring UGK.

In 2000, Jay-Z released The Dynasty: Roc La Familia, which was originally intended to become a compilation album for Roc-A-Fella artists but Def Jam turned into a Jay-Z album. The album helped to introduce newcomer producers The Neptunes, Just Blaze, Kanye West, and Bink, which have all gone on to achieve notable success. This is also the first album where Jay-Z utilizes a more soulful sound than his previous albums. The Dynasty sold over two million units in the U.S. alone.

In 2001, Jay-Z spoke out against Prodigy after he took an issue with Jay-Z's "Money, Cash, Hoes." Prodigy felt that the lyrics alluded disparagingly to his shared dispute with Mobb Deep against Tupac Shakur, Snoop Dogg, and Death Row Records. He later performed the song "Takeover", at Summer Jam 2001, a diss-track about Nas, Prodigy, and Mobb Deep. At the same concert, Jay-Z brought Michael Jackson up on stage with him. A line at the end of "Takeover" referred to Nas, who criticized him on "We Will Survive". Nas responded with a diss of his own, and Jay-Z straightaway added a verse to "Takeover" which dissed Nas and would start a feud between the two rappers. The feud had ended by 2005; Jay-Z stated that record producer Mark Pitts had helped them settle their differences.

On September 11, 2001, Jay-Z released his sixth studio album, The Blueprint, which received a five-mic review from hip-hop magazine The Source. Written in just two days, the album sold more than 427,000 copies, debuted at number one on the Billboard 200 and reached double platinum certification by the Recording Industry Association of America. Eminem guest performed and produced its song, "Renegade". Four tracks were produced by Kanye West. The Blueprint includes the songs "Izzo (H.O.V.A.)", "Girls, Girls, Girls", "Jigga That Nigga", and "Song Cry". As of February 2012, the album had sold 2.7 million copies worldwide. In 2019, The Blueprint was selected by the Library of Congress for preservation in the National Recording Registry for being "culturally, historically, or aesthetically significant".

In October 2001, Jay-Z pleaded guilty to aggravated assault for stabbing record producer Lance Rivera at the Kit Kat Klub in New York City in 1999. Despite Jay-Z's sentence of three years probation for the crime, Rivera later recanted the allegations in 2023.

Jay-Z then collaborated with Chicago singer R. Kelly to release collaborative studio album, The Best of Both Worlds in March 2002. In November of that year, Jay-Z released his seventh studio album The Blueprint2: The Gift & The Curse—a double album. The album debuted on the Billboard 200 at number one, selling over 3 million units solely in the U.S. and surpassing The Blueprint. It yielded a single-disc re-issue, The Blueprint 2.1, which retained half of the songs from the original. Its original release spawned two hit singles, "Excuse Me Miss" and "'03 Bonnie & Clyde", which features Jay-Z's then-girlfriend, Beyoncé, and contained the track "A Dream", featuring Faith Evans and the late Notorious B.I.G.; the re-issue spawned the single "La-La-La", which was a sequel to "Excuse Me Miss" and failed to match its commercial success.

After visiting the south of France, Jay-Z announced work on his eighth studio album, The Black Album at the opening of the 40/40 Club. He worked with several producers including Just Blaze, The Neptunes, Kanye West, Timbaland, Eminem, DJ Quik, 9th Wonder, The Buchanans, and Rick Rubin. Notable songs on the album included "What More Can I Say", "Dirt off Your Shoulder", "Change Clothes", and "99 Problems". The Black Album has sold over 3 million copies in the U.S.

On November 25, 2003, Jay-Z held a concert—billed as a "retirement party" at Madison Square Garden in New York City, which was later the focus of his 2004 documentary, Fade to Black. All proceeds went to charity. Other performers included collaborators the Roots (in the form of his backing band), Missy Elliott, Memphis Bleek, Beanie Siegel, Freeway, Mary J. Blige, Beyoncé, Twista, Ghostface Killah, Foxy Brown, Pharrell Williams and R. Kelly, with appearances by Voletta Wallace and Afeni Shakur, the mothers of the Notorious B.I.G. and Tupac Shakur, respectively. While Jay-Z had attested to a retirement from making new studio albums, various side projects and appearances soon followed. Included in these were a greatest hits record, as well as the release and tour of Unfinished Business, the second collaborative album between Jay-Z and R. Kelly.

In 2004, Jay-Z collaborated with rock group Linkin Park, in which they released their collaborative remix EP Collision Course, which featured mashups of both artists' songs, as well as a concert DVD. The album's only single, "Numb/Encore", went on to win a Grammy Award for Best Rap/Sung Collaboration, and was performed with Linkin Park live at the Grammys, with a special appearance by Paul McCartney, who added verses from the song "Yesterday". The EP sold over 1 million copies in the U.S. Jay-Z was the executive producer of The Rising Tied, the debut album of Fort Minor, the hip hop side project of Linkin Park rapper Mike Shinoda. Jay-Z also planned to retire in 2004.

Later in 2004, Jay-Z was named president of Def Jam Records, which led to Jay-Z, Dash and Biggs selling their remaining interests in Roc-A-Fella Records and Jay-Z taking control of both of the companies. This major industry move was reportedly prompted by disagreements between Jay-Z and Dash as to what direction Roc-A-Fella could undertake.

On October 27, 2005, Jay-Z headlined New York's Power 105.1 annual concert, Powerhouse. The concert's title, "I Declare War," led to intense speculation in the preceding weeks on whom exactly Jay-Z would declare war. As he had previously "declared war" on other artists taking lyrical shots at him at other events, many believed that the concert's title represented an all-out assault by Jay-Z upon his rivals. The theme of the concert was Jay-Z's position as president and CEO of Def Jam, complete with an on-stage mock-up of the Oval Office. Many artists made appearances such as the old roster of Roc-A-Fella records artists, as well as Ne-Yo, Teairra Marí, T.I., Young Jeezy, Akon, Kanye West, Paul Wall, the LOX, and Sean Combs.

At the conclusion of the concert, Jay-Z put many arguments to rest to the surprise of hip hop fans. The most significant development in this show was closure to the infamous hip hop rivalry between Jay-Z and Nas. The two former rivals shook hands and shared the stage together to perform Jay-Z's "Dead Presidents" blended with Nas's song "The World is Yours".

Jay-Z returned with his comeback album on November 21, 2006, titled Kingdom Come. Jay-Z's comeback single, "Show Me What You Got", was leaked on the Internet in early October 2006. The album, which was scheduled for release later on that month, received heavy air-play after its leak, causing the FBI to step in and investigate. Jay-Z worked with video director Hype Williams, and the single's video was directed by F. Gary Gray. The album features production from Just Blaze, Pharrell, Kanye West, Dr. Dre and Coldplay's Chris Martin (single entitled "Beach Chair"). The first week saw 680,000 sales of the CD, enough to be his "biggest sales week ever" as Billboard reported. This album has sold 2 million copies in the U.S. and is certified double platinum.

Jay-Z released his tenth album entitled American Gangster on November 6, 2007. After viewing the Ridley Scott film of the same name, Jay-Z was heavily inspired to create a new "concept" album that depicts his experiences as a street-hustler. The album is not the film's official soundtrack, although it was distributed by Def Jam. Jay-Z's American Gangster depicts his life in correlation to the movie American Gangster. At the start of the album's first single, "Blue Magic", Jay-Z offers a dealer's manifesto while making references to political figures of the late 1980s with the lyric: "Blame Reagan for making me to into a monster, blame Oliver North and Iran-Contra, I ran contraband that they sponsored, before this rhymin' stuff we was in concert." Also notable about the "Blue Magic" music video was Jay-Z flashing €500 notes; Harvard Business School professor Rawi Abdelal called this a "turning point in American pop culture's response to globalization." The album has sold 1 million copies in the U.S. On January 1, 2008, Jay-Z resigned as president of Def Jam.

In winter 2008, it was announced that Jay-Z would become the first major hip hop artist to headline Britain's Glastonbury Festival. Tickets sold out quickly. Former headliner Noel Gallagher of Oasis condemned the festival organizers for choosing Jay-Z to headline a traditionally guitar-driven festival. "I'm sorry, but Jay-Z?" Gallagher asked, swearing. "No chance. Glastonbury has a tradition of, kind of, guitar music, do you know what I mean? And even when they throw the odd curve balls in on a Sunday night—you go, 'Kylie Minogue? I don't know about that', do you know what I mean?—but I'm not having hip hop at Glastonbury, no way, no, no. It's wrong." As controversy mounted, Jay-Z replied, "We don't play guitars, Noel, but hip hop has put in its work like any other form of music. This headline show is just a natural progression. Rap music is still evolving. We have to respect each other's genre of music and move forward." Jay-Z opened his Glastonbury set with a tongue-in-cheek cover of Oasis's iconic song "Wonderwall", and went on to deliver a performance heralded as a successful response to pre-festival criticism. The guitar used in this performance was later shown at the Book of HOV exhibit in the Brooklyn Library.

He also headlined many other summer festivals in 2008, including Roskilde Festival in Denmark, Hove Festival in Norway and O2 Wireless Festival in London. During Kanye West's concert of August 6, 2008, at Madison Square Garden, Jay-Z came out to perform a new song and he and West proclaimed that it was to be on The Blueprint 3. On May 21, 2009, Jay-Z announced he would be parting ways with Def Jam, and had struck a multi-million-dollar deal to sign with Live Nation, with whom he would start his Roc Nation imprint which would serve as a record label, talent/management agency, and music publishing company and also partnered with production team Stargate to start a record label called StarRoc. Jay-Z's 11th studio album The Blueprint 3 was originally to be released on September 11, 2009, but was instead released in North America on September 8, 2009, due to increasing anticipation. Its international release followed on September 14. It is his 11th album to reach No. 1 on the Billboard 200 and surpassed Elvis Presley's previous record. On October 9, 2009, Jay-Z kicked off his tour for The Blueprint 3, during which he supported his new album in North America. In a Shave Magazine review of his performance at Rexall Place in Edmonton, Jake Tomlinson expressed that "It was the type of smooth performance you would expect from the hip-hop superstar." The review gave this performance 4 stars. His North American tour continued until November 22, 2009. At his concert on November 8, 2009, at UCLA's Pauley Pavilion, Rihanna joined him on stage and performed "Hard" for the first time, then performed "Run This Town" with Jay-Z. Among his success, Jay-Z has ventured into producing Broadway shows. Along with Jada Pinkett Smith and Will Smith, Jay-Z helped produce the play Fela!, a musical celebrating the work of the late Nigerian star Fela Kuti. Jay-Z said he was inspired by the power of Kuti's work and his life story, which resulted in his interest to help produce the musical. Fela! is a story about an African pioneer and political activist who made his first moves on the scene during the 1970s.

On January 23, 2010, Jay-Z released a track, "Stranded (Haiti Mon Amour)", with Rihanna, and U2's Bono and The Edge, and performed it at the Hope For Haiti Now telethon. In June 2010, Eminem and Jay-Z announced they would perform together in a pair of concerts in Detroit and New York. The event was dubbed The Home & Home Tour. The first two concerts rapidly sold out, prompting the scheduling of an additional show at each venue. Jay-Z was the supporting act for U2 on the Australian and New Zealand leg of their U2 360° Tour, beginning in Auckland, New Zealand, in November 2010, followed by Melbourne, Sydney, Brisbane and Perth in December.

Jay-Z would later appear with Kanye West on Watch the Throne, a full-length LP with origins as a five-track EP. Recording sessions for the album took place at various recording locations and began in November 2010. The first single released for the project was "H•A•M". The track was co-produced by Lex Luger and West himself. The track ended up being on the deluxe edition of the album. The follow-up to that was the second single "Otis", which premiered on Funkmaster Flex's Hot 97 radio show, and was later released to the iTunes Store eleven days later. The song's existence, along with several other tracks from the album, was confirmed during a listening session hosted by Jay-Z. The album was first released on the iTunes Store, five days prior to its being released in physical format, a strategy Jay-Z later said was used to block an internet leak. It debuted at No. 1 on the iTunes Store in 23 countries. It also broke Coldplay's record for most albums sold in one week on the online retailer, selling 290,000 copies on iTunes alone. It held that record until Lil Wayne's Tha Carter IV was released twenty-one days later, selling 10,000 copies more. It debuted on the U.S. Billboard 200 chart at No. 1, selling 436,000 copies in its first week. The album received generally positive reviews. Jay-Z and West later gave a surprise performance of "Otis" at the 2011 MTV Video Music Awards.

In May 2012, Jay-Z and former Philadelphia mayor Michael A. Nutter announced Jay-Z as the curator and the headliner for the first annual "Budweiser Made in America" festival at Fairmount Park in Philadelphia on September 1 and 2, 2012. The performance was produced by Live Nation and assembled an eclectic lineup of "rock, hip hop, R&B, Latin music and dance" musicians. Jay-Z and Rihanna were the two main headlining acts for BBC Radio 1's 2012 Hackney Weekend music festival on June 23 to 24. Jay-Z opened his set with an appearance from Rihanna, they performed "Run this Town". On September 6, "Clique" was released, a single from the album "Cruel Summer", by GOOD Music. Kanye West and Big Sean starred alongside Jay-Z on the track. Jay-Z took the subway to his sold-out show at The Barclays Center on October 6, 2012. In December 2012, Coldplay performed with Jay-Z at the Barclays Center in Brooklyn.

On September 23, 2010, Q-Tip confirmed working on Jay-Z's follow-up album to The Blueprint 3, saying the album was to hit stores by spring 2011. In May 2012 it was reported that Jay-Z would work on new music with Roc Nation producer Jahlil Beats. Beats told XXL magazine: "Me and Jay-Z been going back and forth. He picked a couple of my joints that he's working on. I don't even wanna say too much about Jay, but we definitely working on some stuff. I haven't even sent him a bunch of beats. I sent him my favorite stuff. He hit me right back like, 'Yo, I'ma go in on this,' or, 'I like this.'" The album was named one of the most anticipated albums of 2013 by Complex Magazine, MTV, and XXL. The album was produced by Jahlil Beats, Kanye West, Rick Rubin, Swizz Beatz, Timbaland, and Pharrell Williams. Jay-Z also co-produced and performed on Justin Timberlake's comeback single "Suit & Tie" from his third studio album The 20/20 Experience, the song itself was produced by both Jay-Z and Timberlake's mutual friend, Timbaland. In July 2013, Timberlake and Jay-Z embarked on the co-headlining Legends of the Summer Stadium Tour.

During the fifth game of the 2013 NBA Finals, Carter announced his twelfth studio album, Magna Carta Holy Grail, and was released on July 4, 2013. Not long after, Jay-Z confirmed that the hyphen in his stage name would be left out and officially stylized in all capital letters. Magna Carta Holy Grail debuted at number one on the Billboard 200 and sold 528,000 copies in its first week, which bypassed its predicted debut in the range of 350,000 to 400,000. In December 2013, it was announced that Jay-Z had received nine nominations at the 2014 Grammy Awards, more than any other artist. Jay-Z appeared on his wife Beyoncé's self-titled fifth studio album, Beyoncé, with a feature on the song "Drunk in Love". They performed this song together at the 56th Annual Grammy Awards opening. The song and its accompanying album would later win three Grammy Awards including Best R&B Performance at the 2015 ceremony. In 2016, he won a lawsuit for the song "Made in America" with Kanye West featuring Frank Ocean against Joel McDonald.

In early June 2017, posters were displayed in New York City and Los Angeles, and banner ads were placed on the Internet promoting a Tidal-related project titled 4:44. A teaser ad was aired during the NBA Finals on June 7 featuring actors Mahershala Ali, Lupita Nyong'o and Danny Glover in a one-minute video, ending in "4:44 – 6.30.17, Exclusively on Tidal". On June 18, the project was confirmed to be a new Jay-Z album, and a clip featuring a song titled "Adnis" was posted on Sprint's YouTube page. 4:44 was released through Roc Nation and Universal Music Group, as an exclusive to Sprint and Tidal customers. The album is the first in a planned series of music exclusives from the Sprint–Tidal partnership. For a short time, on July 2, the album was made available for free digital download in Tidal's site. A physical edition was released on July 7, including three additional tracks. On the same day, the album was made available to other streaming platforms, such as Apple Music, Google Play Music and Amazon Music.

The album received widespread acclaim from critics, who praised its emotional and personal content. On July 5, the album was certified Platinum by the Recording Industry Association of America (RIAA), in recognition of one million copies purchased by Sprint and offered to consumers as free downloads. It debuted at number one on the U.S. Billboard 200, making it Jay-Z's 13th consecutive studio album to top the chart. The album spawned two singles, the title track "4:44" and "Bam", as well as several music videos, directed by a variety of high-profile collaborators. The album received a Grammy Award nomination for Album of the Year, while the title track was nominated for Song of the Year and "The Story of O.J." was nominated for Record of the Year at the 60th Annual Grammy Awards. Two years later, he became hip-hop's first artist to achieve billionaire status.

On June 6, 2018, Jay-Z and Beyoncé kicked-off the On the Run II Tour in Cardiff, United Kingdom. Ten days later, at their final London performance, the pair unveiled Everything Is Love, their much-awaited joint studio album, credited under the name The Carters. The pair also released the video for the album's lead single, "Apeshit", on Beyoncé's official YouTube channel. The song won two awards from eight nominations at the 2018 MTV Video Music Awards.

In 2021, Jay-Z was inducted into the Rock and Roll Hall of Fame along with fellow rapper LL Cool J. He also appeared on the song "Jail" on Kanye West's 2021 album Donda, which went on to win Grammy Award for Best Rap Song at the 64th Annual Grammy Awards and on the song "Love All" from Drake's 2021 album Certified Lover Boy. In 2022, his first feature was a collaboration with fellow rapper Pusha T, "Neck & Wrist" featuring Pharrell Williams from Pusha T's album, It's Almost Dry. His feature was succeeded by a four-minute guest appearance on DJ Khaled's album title track, "God Did". He also was awarded the Primetime Emmy Award for Outstanding Variety Special (Live), as a producer for the Super Bowl LVI halftime show. In 2023, Billboard and Vibe published a list of the 50 greatest rappers of all time, where they claimed Jay-Z is the greatest rapper of all time. The list was met with widespread backlash. That same year, the Brooklyn Library featured the Book of HOV exhibit. The showcase included artifacts commemorating Jay-Z's career. The next year, the exhibit was turned into a book, The Book of HOV: A Tribute to Jay-Z. Similar to the exhibit, the physical book recounted Jay-Z's life and career, including images, interviews, and professional insights.

In 2026, Jay-Z released "Dead Presidents" on streaming services and a limited-edition vinyl, CD and cassette tape version on his website, to celebrate the 30th anniversary of his debut studio album Reasonable Doubt. He also added the umlaut to his stage name, which was a callback to the artwork of the album. In 2026, The New York Times named Jay-Z one of the "30 Greatest Living American Songwriters."

In March 2026, Jay-Z announced a three shows at Yankee Stadium scheduled for July 2026 to commemorate the 25th and 30th anniversaries of his albums The Blueprint and Reasonable Doubt. In May 2026, Jay-Z headlined the Roots Picnic festival, marking his first headlining set in six years. In June 2026, Jay-Z and Roc Nation announced the Jay-Z 30 Tour concert series, with shows scheduled in Paris in September and Los Angeles in October to commemorate the 30th anniversary of his debut album Reasonable Doubt.

Jay-Z says his earliest exposure to music was through his parents' record collection, which was mostly of soul artists such as Marvin Gaye and Donny Hathaway. He says "I grew up around music, listening to all types of people... I'm into music that has soul in it, whether it be rap, R&B, pop music, whatever. As long as I can feel their soul through the wax, that's what I really listen to." He often uses excerpts from these artists as samples in his work, particularly in the Kanye West productions included on The Blueprint.