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Tupac gets upset with fan and Argues with John Singleton
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Shakur's professional entertainment career began in the early 1990s, when he debuted his rapping skills in a vocal turn 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 of the same name. 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. Later, he released his first solo album, 2Pacalypse Now. Though the album did not generate any "Top Ten" hits, 2Pacalypse Now is hailed 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.[39] Although the album was originally released on Interscope Records, rights of it are now owned by Amaru Entertainment. The album's name is a reference to the 1979 film Apocalypse Now.

The album generated significant controversy. Dan Quayle criticized it after a Texas youth's defense attorney claimed he was influenced by 2Pacalypse Now and its strong 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 the previous one debuting on number 24 on the Billboard 200. The album contains many tracks emphasizing Shakur's political and social views. This album had more commercial success than its predecessor, and there were noticeable differences in production. While Shakur's first effort had an indie-rap-oriented sound, this album was considered his "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 his tenth-biggest selling album, with 1,366,000 units moved as of 2004.