Legal issues

Even as he garnered attention as a rapper and actor, Shakur gained notoriety for his conflicts with the law. In October 1991, he filed a $10 million civil suit against the law enforcement of the Oakland Police Department, alleging they brutally beat him for jaywalking. The suit was later settled for $42,000.

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 passed by them or "almost struck them", after which the Whitwells began an altercation with the driver and passengers, which was then joined by a second passing car. One officer was shot in the buttocks, and the other in the leg, back, or abdomen, according to varying news reports. There were no other injuries, but Mark was charged with firing at Shakur's car and later lying to the police during the investigation, and Shakur with the shooting, until prosecutors decided to drop all charges against all parties.

In December 1993, Shakur and others were charged with sexually abusing a woman in a hotel room. According to the complaint, Shakur sodomized the woman and then encouraged his friends to sexually abuse her. Shakur vehemently denied the charges. He had prior relations days earlier with the woman who was pressing the charges against him. She performed oral sex on him on a club dance floor and the two later had consensual sex in his hotel room. The allegations were made after she revisited his hotel room for the second time where she engaged in sexual activity with his friends and alleged that Shakur and his entourage had mass raped her, saying to him while leaving, "Why you let them do this to me?" Shakur stated he had fallen asleep shortly after she arrived and later awoke to her accusations and legal threats. He later said he felt guilty for leaving her alone and did not want anyone else to go to jail, but at the same time he did not want to go to jail for a crime he didn't commit. Shakur was convicted of sexual abuse. In sentencing Shakur to one-and-a-half years in a correctional facility, the judge described the crime as "an act of brutal violence against a helpless woman".

In 1994, he was convicted of attacking a former employer while on a music video set. He was sentenced to 15 days in jail with additional days on a highway work crew, community service, and a $2000 fine. Later that year he began dating Madonna, who wanted to have his child; the two would continue to date until friends of Shakur encouraged him to end the relationship. In 1995, a wrongful death suit was brought against Shakur for a 1992 shooting that killed Qa'id Walker-Teal, a six-year old of Marin City. The child had been the victim of a stray bullet in a shootout between Shakur's entourage and a rival group, though the ballistics tests proved the bullet was not from Shakur or any members of his entourage's guns. Criminal charges were not sought, and Shakur settled with the family for an amount estimated between $300,000 and $500,000. After serving part of his sentence upon a conviction, he was released on bail pending his appeal. On April 5, 1996, a judge sentenced him to serve 120 days in jail for violating terms of probation.