Tupac's 25 Most Infamous Moments

20 years later, nobody made headlines like Pac.

Bruised and Battered - After the release of Tupac’s first album, 2Pacalypse Now, in which the rapper told stories of the trials and tribulations of growing up young, Black and male in the inner cities of America, Tupac was beaten by police in Oakland, California. The rapper said that he had never had any such encounter with police before rapping about police brutality on his record. Photos of the incident show Tupac’s bruised face after having been pushed face down in the street and arrested for jaywalking. He sued the Oakland Police Department and was awarded a small sum.
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Showing Out - Tupac was set to star in the LA coming of age drama Menace II Society, the Hughes brothers’ first feature film.  But after a quarrel on set, resulted in Tupac attacking Allen Hughes, Tupac was released from his contract. The rapper later went on Yo! MTV Raps and animatedly discussed the incident. The footage was later used in the trial against him. He was sentenced to 15 days in jail. (Photo: MTV)
Lyrical Drive-by - Still arguably, one of the hardest diss records to date, the single, "Hit'em Up" goes in on almost every prominent East coast rapper. Only adding fuel to the fire of the media hyped coastal feud. Tupac takes aim at the Notorious BIG, Mobb Deep and many more.(Photo: Death Row/Interscope Records)02f/35/arod/15326/P2506_184

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More Legal Woes - One year after a Texas teen shot and killed a state trooper while allegedly listening to 2Pacalypse Now, Tupac faced charges of shooting an off-duty police officer in Atlanta. In late 1993, after it was revealed that the officer had lied in his testimony, charges were dropped against all parties involved. (Photo: Gerald Herbert/NY Daily News Archive via Getty Images)

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