987–93: Beginnings and rise to fame

Before using his first name as his rap name, Shakur went by the alias MC New
York when starting his career in Baltimore. Although Shakur began recording in
1987, his professional entertainment career did not take off until the early 1990s
when he debuted in Digital Underground's "Same Song" from the soundtrack to
the 1991 film Nothing but Trouble, and also appeared with the group in the film.
The song was later released as the lead song of the Digital Underground extended
play (EP) This Is an EP Release, the follow-up to their debut hit album Sex Packets.
Shakur appeared in the accompanying music video. After his rap debut, he
performed with Digital Underground again on the album Sons of the P. Shakur
went on to feature Shock G and Money-B from Digital Underground in his track "I
Get Around", which ranked #11 on the U.S. Billboard Hot 100.

In November 1991, Shakur released his debut solo album, 2Pacalypse Now.
Though the album did not generate any hit singles, 2Pacalypse Now has been
acclaimed by many critics and fans for its underground feel, with many rappers
such as Nas, Eminem, Game, and Talib Kweli having pointed to it as inspiration.[38]
Although the album was originally released on Interscope Records, the rights to its
distribution are now owned by Amaru Entertainment, the label owned by Shakur's
mother. The album's name is a reference to the 1979 film Apocalypse Now.

2Pacalypse Now generated significant controversy for numerous reasons. The

songs "Trapped" and "Brenda's Got a Baby" were widely noted for their poetic
qualities but also offered strong critiques of unjust social policies. [39] Dan Quayle
criticized the album after a Texas youth's defense attorney claimed he was
influenced by 2Pacalypse Now and its theme of police brutality before shooting a
state trooper. Quayle said, "There's no reason for a record like this to be released. It
has no place in our society." Shakur stated that he felt he had been
misunderstood.[40] He said, "I started out saying I was down for the young black
male, you know, and that was gonna be my thang," Shakur said. "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. I just
figured since I lived that life I could do that, I could rap about that." [41][42] The
record was important in showcasing Shakur's political conviction and his focus on
lyrical prowess. On MTV's Greatest Rappers of All Time list, 2Pacalypse Now was
listed as one of Shakur's "certified classic" albums, along with Me Against the World,
All Eyez on Me and The Don Killuminati: The 7 Day Theory. 2Pacalypse Now went
on to be certified Gold by the RIAA. It featured three singles: "Brenda's Got a Baby",
"Trapped", and "If My Homie Calls".
His second studio album, Strictly 4 My N.I.G.G.A.Z..., was released in February
1993. The album did better than its predecessor both critically and commercially,
debuting at number 24 on the Billboard 200. The album contains many tracks
emphasizing Shakur's political and social views, and there are noticeable
differences in production from his first effort. While 2Pacalypse Now had an
indie-rap-oriented sound, Strictly 4 My N.I.G.G.A.Z... is generally considered
Shakur's "breakout" album. It spawned the hits "Keep Ya Head Up" and "I Get
Around" and reached platinum status. On vinyl, Side A (tracks 1–8) was labeled
the "Black Side" and Side B (tracks 9–16) the "Dark Side". It is Shakur's
tenth-biggest selling album, with 1,366,000 units moved as of 2004. [43]

1993–95: Acting and rise to prominence

The test pressing single for "Dear Mama": the platinum single is among the top ranked
songs in hip-hop history.

In late 1993, Shakur formed the group Thug Life with a number of his friends,
including Big Syke (Tyruss Himes), Macadoshis (Diron Rivers), his stepbrother
Mopreme Shakur, and the Rated R (Walter Burns). The group released their only
album Thug Life: Volume 1 on September 26, 1994, which went gold. The album
featured the single "Pour Out a Little Liquor", produced by Johnny "J" Jackson,
who went on to produce a large part of Shakur's album All Eyez on Me. The group
usually performed their concerts without Shakur.[44] The album was originally
released by Shakur's label Out Da Gutta Records, though Amaru Entertainment
has since gained the rights to it. Among the notable tracks are "Bury Me a G",
"Cradle to the Grave", "Pour Out a Little Liquor" (which also appears on the
soundtrack to the 1994 film Above the Rim), "How Long Will They Mourn Me?"
and "Str8 Ballin'". As a result of criticism of gangsta rap at the time, the original
version of the album was scrapped and re-recorded with many of the original
songs being cut. The album contains ten tracks because Interscope Records felt
many of the other recorded songs were too controversial to release. Although the
original version of the album was not completed, Shakur performed the planned
first single from the album, "Out on Bail" at the 1994 Source Awards. [45] Thug Life:
Volume 1 was certified Gold. The track "How Long Will They Mourn Me?" later
appeared on 2Pac's posthumous Greatest Hits album.[46]

Shakur's third album, Me Against The World, was released in March 1995 and
was very well-received, with many calling it the magnum opus of his career. It is
considered one of the greatest and most influential hip-hop albums of all time. It is
Shakur's fourth-best-selling album with 3,524,567 copies sold in the United
States as of 2011.[47] Me Against the World won best rap album at the 1996 Soul
Train Music Awards.[48]