Shakur began recording under the stage name MC New York in 1988.^[66] That year, he began attending the poetry classes of Leila Steinberg, and she soon became his manager.^[67][61] Steinberg organized a concert for Shakur and his rap group Strictly Dope. Steinberg managed to get Shakur signed by Atron Gregory, manager of the rap group Digital Underground.^[61] In 1990, Gregory placed him with the Underground as a roadie and backup dancer.^[61][68]

Shakur debuted under the stage name 2Pac on Digital Underground, under a new record label, Interscope Records, on the group’s January 1991 single “Same Song“. The song was featured on the soundtrack of the 1991 film Nothing but Trouble, starring Dan Aykroyd, John Candy, Chevy Chase, and Demi Moore.^[61] The song opened the group’s January 1991 EP titled This Is an EP Release,^[61] while Shakur appeared in the music video.

At the request of Steinberg, Digital Underground co-founder Jimi “Chopmaster J” Dright worked with Shakur, Ray Luv and Dize, a DJ, on their earliest studio recordings. Dright recalls that Shakur did not work well as part of a group, and added, “this guy was on a mission. From day one. Maybe he knew he wasn’t going to be around seven years later.”^[69]

From 1988 to 1991, Dright and Digital Underground produced Shakur’s earliest work with his crew at the time, Strictly Dope.^[70] The recordings were rediscovered in 2000 and released as The Lost Tapes: Circa 1989.^[71] Afeni Shakur sued to stop the sale of the recordings but the suit was settled in June 2001 and rereleased as Beginnings: The Lost Tapes 1988–1991.^[71][72]

Shakur’s early days with Digital Underground made him acquainted with Randy “Stretch” Walker, who along with his brother, dubbed Majesty, and a friend debuted with an EP as a rap group and production team, Live Squad, in Queens, New York.^[73] Stretch was featured on a track of the Digital Underground’s 1991 album Sons of the P. Becoming fast friends, Shakur and Stretch recorded and performed together often.^[73]

Shakur’s debut album, 2Pacalypse Now—alluding to the 1979 film Apocalypse Now—arrived in November 1991. Some prominent rappers—like Nas, Eminem, Game, and Talib Kweli—cite it as an inspiration.^[74] Aside from “If My Homie Calls”, the singles “Trapped” and “Brenda’s Got a Baby” poetically depict individual struggles under socioeconomic disadvantage.^[75]

U.S. Vice President Dan Quayle said, “There’s no reason for a record like this to be released. It has no place in our society.” Tupac, finding himself misunderstood,^[51] explained, in part:

I just wanted to rap about things that affected young black males. When I said that, I didn’t know that I was gonna tie myself down to just take all the blunts and hits for all the young black males, to be the media’s kicking post for young black males.^[76][77]

2Pacalypse Now was certified Gold, half a million copies sold. The album addresses urban Black concerns said to remain relevant to the present day.^[61]

Shakur’s second album, Strictly 4 My N.I.G.G.A.Z…, was released in February 1993.^[78] A critical and commercial success, it debuted at No. 24 on the pop albums chart, the Billboard 200.^[79] An overall more hardcore album, it emphasizes Tupac’s sociopolitical views, and has a metallic production quality. The song “Last Wordz” features Ice Cube, co-writer of N.W.A’s “Fuck tha Police“, who in his own solo albums had newly gone militantly political, and gangsta rapper Ice-T, who in June 1992 had sparked controversy with his band Body Count‘s track “Cop Killer“.^[78]

In its vinyl release, side A, tracks 1 to 8, is labeled the “Black Side”, while side B, tracks 9 to 16, is the “Dark Side”.^{[citation needed]} The album carries the single “I Get Around“, a party anthem featuring Digital Underground’s Shock G and Money-B, which became Shakur’s breakthrough, reaching No. 11 on the pop singles chart, the Billboard Hot 100.^[79] The album also carries the optimistic compassion of another hit, “Keep Ya Head Up“, an anthem for women’s empowerment.^[80] The album was certified Platinum, with a million copies sold. As of 2004, among Shakur albums, including posthumous and compilation albums, Strictly 4 My N.I.G.G.A.Z… was 10th in sales at about 1,366,000 copies.^[81]

In late 1993, Shakur formed the group Thug Life with Tyrus “Big Syke” Himes, Diron “Macadoshis” Rivers, his stepbrother Mopreme Shakur, and Walter “Rated R” Burns.^[82][83]

Thug Life released its only album, Thug Life, Volume I, on October 11, 1994, which is certified Gold. It carries the single “Pour Out a Little Liquor”, produced by Johnny “J” Jackson, who would also produce much of Shakur’s album All Eyez on Me. The track also appears on the Above the Rim soundtrack.^[84] Due to gangsta rap being under heavy criticism at the time, the album’s original version was scrapped, and the album redone with mostly new tracks. Still, along with Stretch, Tupac would perform the first planned single, “Out on Bail”, which was never released, at the 1994 Source Awards.^[85]

In 1993, while visiting Los Angeles, the Notorious B.I.G. asked a local drug dealer to introduce him to Shakur and they quickly became friends. The pair would socialize when Shakur went to New York or B.I.G. to Los Angeles.^[86] During this period, at his own live shows, Shakur would call B.I.G. onto stage to rap with him and Stretch.^[86] Together, they recorded the songs “Runnin’ from tha Police” and “House of Pain”.

Reportedly, B.I.G. asked Shakur to manage him, whereupon Shakur advised him that Sean Combs would make him a star.^[86] Yet in the meantime, Shakur’s lifestyle was comparatively lavish to B.I.G. who had not yet established himself.^[86] Shakur welcomed B.I.G. to join his side group Thug Life, but he would instead form his own side group, the Junior M.A.F.I.A., with his Brooklyn friends Lil’ Cease and Lil’ Kim. Shakur had a falling out with B.I.G. after Shakur was shot at Quad Studios in 1994.^[87]

Shakur’s third album, Me Against the World, was released while he was incarcerated in March 1995.^[88] It is now hailed as his magnum opus, and commonly ranks among the greatest, most influential rap albums.^[88] The album debuted at No. 1 on the Billboard 200 and sold 240,000 copies in its first week, setting a then record for highest first-week sales for a solo male rapper.^[89][90]

The lead single, “Dear Mama“, was released in February 1995 with “Old School” as the B-side.^[91] It is the album’s most successful single, topping the Hot Rap Singles chart, and peaking at No. 9 on the Billboard Hot 100.^[9] In July, it was certified Platinum.^[92] It ranked No. 51 on the year-end charts. The second single, “So Many Tears“, was released in June 1995,^[93] reaching No. 6 on the Hot Rap Singles chart and No. 44 on Hot 100.^[9] The final single, “Temptations“, was released in August 1995.^[94] It reached No. 68 on the Hot 100, No. 35 on the Hot R&B/Hip-Hop Singles & Tracks, and No. 13 on the Hot Rap Singles.^[9] Several celebrities showed their support for Shakur by appearing in the music video for “Temptations”.^[95]

Shakur won best rap album at the 1996 Soul Train Music Awards.^[96] In 2001, it ranked 4th among his total albums in sales, with about 3 million copies sold in the U.S.^[97]

While Shakur was imprisoned in 1995, his mother was about to lose her house. Shakur had his wife Keisha Morris contact Death Row Records founder Suge Knight in Los Angeles.^[86] Reportedly, Shakur’s mother promptly received $15,000.^[86] After an August visit to Clinton Correctional Facility in northern New York state, Knight traveled southward to New York City to attend the 2nd Annual Source Awards ceremony. Meanwhile, an East Coast–West Coast hip-hop rivalry was brewing between Death Row and Bad Boy Records.^[98] In October 1995, Knight visited Shakur in prison again and posted $1.4 million bond.^[99] Shakur returned to Los Angeles and joined Death Row with the appeal of his December 1994 conviction pending.^[99]

Shakur’s fourth album, All Eyez on Me, arrived on February 13, 1996.^[100] It was rap’s first double album—meeting two of the three albums due in Shakur’s contract with Death Row—and bore five singles.^[101] The album shows Shakur rapping about the gangsta lifestyle, leaving behind his previous political messages. With standout production, the album has more party tracks and often a triumphant tone.^[9] Music journalist Kevin Powell noted that Shakur, once released from prison, became more aggressive, and “seemed like a completely transformed person”.^[102]

As Shakur’s second album to hit No. 1 on both the Top R&B/Hip-Hop Albums chart and the pop albums chart, the Billboard 200,^[9] it sold 566,000 copies in its first week and was it was certified 5× Multi-Platinum in April.^[103] The singles “How Do U Want It” and “California Love” reached No. 1 on the Billboard Hot 100.^[104] Death Row released Shakur’s diss track “Hit ‘Em Up” as the non-album B-side to “How Do U Want It”. In this venomous tirade, the proclaimed “Bad Boy killer” threatens violent payback on all things Bad Boy — B.I.G., Sean Combs, Junior M.A.F.I.A., the company — and on any in the East Coast rap scene, like rap duo Mobb Deep and rapper Chino XL, who allegedly had commented against Shakur about the dispute.^[105]

All Eyez on Me won R&B/Soul or Rap Album of the Year at the 1997 Soul Train Music Awards.^[106] At the 1997 American Music Awards, Shakur won Favorite Rap/Hip-Hop Artist.^[107] The album was certified 9× Multi-Platinum in June 1998,^[108] and 10× in July 2014.^[109]

At the time of his death, a fifth solo album was already finished, The Don Killuminati: The 7 Day Theory, under the stage name Makaveli. It had been recorded during the summer of 1996 and released that year.^[110][111] The lyrics were written and recorded in three days, and mixing took another four days. In 2005, MTV.com ranked The 7 Day Theory at No. 9 among hip-hop’s greatest albums ever,^[112] and by 2006 a classic album.^[113] Its singular poignance, through hurt and rage, contemplation and vendetta, resonate with many fans.^[114]

According to George “Papa G” Pryce, Death Row Records’ then director of public relations, the album was meant to be “underground”, and was not intended for release before the artist was murdered.^{[115][unreliable source?]} It peaked at No. 1 on Billboard‘s Top R&B/Hip-Hop Albums chart and on the Billboard 200,^[116] with the second-highest debut-week sales total of any album that year.^[117] On June 15, 1999, it was certified 4× Multi-Platinum.^[118]

Later posthumous albums are archival productions, these albums are:

• R U Still Down? (1997)
• Greatest Hits (1998)
• Still I Rise (1999)
• Until the End of Time (2001)
• Better Dayz (2002)
• Loyal to the Game (2004)
• Pac’s Life (2006)^[119]