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Ekim 1993'te, Shakur came upon two off-duty police officers whom he perceived as harassing a black motorist on the side of the road in Atlanta. Shakur got into a fight with them and shot both officers (one in the leg, one in the buttocks). He faced serious charges until it was discovered that both officers were intoxicated during the incident and were using weapons stolen out of an evidence locker. The charges against Shakur were dismissed. 

Kasım1993'te, Shakur, otel odasında bir kadına taciz etmekle suçlandı. Tupac'sa kadın hayranıyla bir kulüpte tanıştığını, dans pistinde oral seks yaptıklarını ve sonra da otel odasına gittiklerini söyledi.Ertesi gece,  she visited him before he was set to do a show and was giving him a massage in a hotel room. Some friends who were with him that night interrupted the couple, wanting to enjoy the woman's attentions themselves. Shakur claimed to have left the room disgusted and went to take a nap. The girl, disagreeing with his account, accused him of encouraging the three men, pulling her hair, and sodomy. 

On February 7, 1995, Shakur was sentenced to four and a half years in prison for "forcibly touching the buttocks", though he vehemently denied any wrongdoing. Since the time Tupac died in 1996, he has had people fighting over his estate. It started at one if his concerts, Jacquelyn McNealy, 27 was hit by a stray bullet. She was then awarded $16.6 million of Tupac�s money, even though Tupac was never properly notified on the lawsuit. His label, Death Row wanted $7 million of his money until a temporary settlement last week. C. Delores Tucker who said Tupac used a derogative epithet sued him. She and her husband claimed Tupac ruined their sex life because of his lyrics. Tucker was against gangsta rap from the beginning and filed a lawsuit some time after his death