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.
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." The record was important in showcasing 2Pac'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 2Pac'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". 2Pacalypse Now can be found in the Vinyl Countdown and in the instruction manual for Grand Theft Auto: San Andreas, along with the track "I Don't Give a Fuck," which appeared on the in-game radio station, Radio Los Santos.
In October 1991, Tupac filed a $10 million civil suit against the Oakland Police Department, alleging they brutally beat him for jaywalking. On August 22, 1992, in Marin City, Shakur performed at an outdoor festival, and stayed for an hour afterwards signing autographs and pictures. A confrontation occurred in which someone drew a Colt Mustang, and accidentally dropped it. As it was picked up, a bullet discharged. About 100 yards away, Qa'id Walker-Teal, a 6-year-old, was pedaling his bicycle at a school playground nearby when a bullet struck him in the forehead and killed him.
Although the fatal slug was matched by police to a .38-caliber pistol registered to Shakur, and his half-brother, Maurice Harding was initially arrested on suspicion of firing the weapon, no charges were filed. Marin County prosecutors have said they were stymied by a lack of witnesses. Charges were dropped when Shakur agreed to pay a $300,000 - $500,000 settlement to the parents The police "rescued" them and took the two into custody, who were soon released without charge for lack of evidence.
In 1995, a wrongful death suit was brought against Shakur by Qa'id's mother. Ballistics tests proved the bullet that killed the boy was not from Shakur's or any members of his entourage's gun. Shakur's attorney stated that the festival was a "nasty situation," and his client was saddened by the death of the young boy. Shakur's record company settled the lawsuit for an undisclosed amount, reportedly between $300,000 and $500,000.
In October 1993, in Atlanta, two brothers and off-duty police officers, Mark and Scott Whitwell, were with their wives celebrating Mrs. Whitwell's recent passing of the state bar examination. As they crossed the street, a car with Shakur inside passed by them or "almost struck them." The Whitwells began an altercation with the driver, Shakur and the other passengers, which was joined by a second passing car. Shakur shot one officer in the buttocks, and the other in the leg, back, or abdomen, according to varying news reports. There were no other injuries. Mark Whitwell was charged with firing at Shakur's car and later lying to the police during the investigation; Shakur was charged with the shooting; the prosecutors decided to drop all charges against all parties.
In November 1993, Shakur and others were charged with sexually assaulting a woman in a hotel room. Shakur denied the charges. According to Shakur, he had prior relations days earlier with the woman that were consensual. The complainant claimed sexual assault after her second visit to Shakur's hotel room; she alleged that Shakur and his entourage raped her. In the ensuing trial, Shakur was convicted of sexual abuse. In sentencing Shakur to 1½–4½ years in prison, the judge described the crime as "an act of brutal violence against a helpless woman." After serving part of his sentence, Shakur was released on bail pending appeal. On April 5, 1996, a judge sentenced him to serve 120 days in jail for violating terms of his release on bail.
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