Tupac Shakur's Craziest Moments


There may be no figure in hip-hop history more polarizing than Tupac Shakur. While posthumously he can do no wrong, when 'Pac was alive, a storm cloud of drama seemed to always follow the man. In time, like any cherished artist's legacy, Tupac's exploits have gained an almost mythic patina. But the “Hit ‘Em Up” rapper holds the distinction of being involved in altercations, incidents and confrontations that were truly jaw-dropping and borderline outlandish. Shoot outs with cops, dodging bullets, knocking out movie directors, all part of 'Pac’s lore. As Tupac Month continues, decided to put together some of 'Pac’s craziest moments.—XXL Staff

Stray Bullet


After a performance in Marin City, California on August 22, 1992, 'Pac stuck around to sign autographs but ended up getting into a heated exchange with some local tough guys. 'Pac allegedly pulled out a gun, but somehow it fell before he fired the weapon. When someone else picked up the gun, it accidentally discharged. Coincidentally, 6-year-old Qa'id Walker-Teal, who was riding his bike nearby, got shot in the head and killed by a stray bullet. Some news outlets reported that 'Pac was to blame, and he settled a wrongful death suit with the child’s family, but ballistic tests proved it was not a bullet from his gun that killed the boy.

Tupac Shoots It Out With Po Po


In October 1993 in Atlanta, Tupac saw what he felt was a motorist being harassed by a couple of police officers and he stopped to intervene. What happened next is a matter of opinion, but an altercation occurred where one cop shot at 'Pac, missed and the late rapper returned fire, shooting one of the cops in the abdomen and the other in the buttocks. But get this, the charges against 'Pac were eventually dropped considering the cops were intoxicated and the guns they had were taken from an evidence room.

When Thugs Cry


Per Maya Angelou, Tupac and another man got in a heated argument on the second day of shooting on the set of Poetic Justice. After several failed attempts—‘Pac reportedly kept yelling as the legendary author tried to speak with him—Angelou took ‘Pac to the side and told him, “Do you how much you’re needed. Do you know what you mean to us. Do you know that a hundred years of struggle have been for you? “ Angelou said she put her arm around ‘Pac and he started to cry.

An AIDS Test?

An AIds Test (93)

Tupac was an accomplished thespian. In 1993, he appeared on The Arsenio Hall Show to promote a new film he was starring opposite Janet Jackson titled Poetic Justice. During the interview Tupac told Arsenio that Janet required he take an AIDS test before she would agree to kiss him on screen. Allegedly, after kissing Q-Tip in the same film (blink and you might miss him), she caught a cold. Needless to say, 'Pac wasn’t having it.

Head On the Dance Floor

lHead On the Dance Floor

Years before N.O.R.E. bragged about “getting head in the whip and not crashing it,” 'Pac was allegedly, umm, “blessed” on the dance floor at an NYC nightspot called Nell’s. Although she admitted having sexual relations with 'Pac later that night, she vehemently denied performing oral sex on at at Nell’s. Unfortunately, the same woman that showed her affection for 'Pac on the dance floor, would accuse him, along with several associates, of sexually assaulting her in hotel room a couple of few days later.

It Wasn't Me

Rape Charges '93

Only a month after shooting two off-duty police officers in Atlanta, Tupac was charged with sexually assaulting Ayanna Jackson. Jackson claimed Shakur sodomized her and then gang banged him with his entourage. ‘Pac denied the charges, Jackson gave him oral sex on a club dance floor and that they later had consensual sex in his hotel room.

Vibe Magazine Straight Jacket Cover


Tupac’s Vibe Magazine stories were the stuff of legend since he rarely if ever minced his words. The most iconic of the covers is easily the first, where Tupac is photographed wearing a straight jacket on the front of the magazine’s February 1994 issue. The tagline read “Is Tupac Crazy or Just Misunderstood” and the story was penned by esteemed scribe, and now politician, Kevin Powell.

2 Minute Fight, 15 Days in Jail

Hughes Brothers Assault 94

In 1994, Albert and Allen Hughes filed a lawsuit against Shakur for assaulting them at a music video shoot. Legend has it that the altercation took place because ‘Pac was displeased with the role he’d been given on the brothers’ Menace II Society. Tupac was replaced in the wake of the assault. ‘Pac appeared on The Arsenio Hall Show the night before the sentencing and told Arsenio the incident partly had to do with John Singleton, who directed ‘Pac in Poetic Justice. He was eventually sentenced to 15 days in jail for the beating and another incident that took place on the eve of the sentencing.

Quad Studio Shooting

Quad Studio Shooting 94

Easily the most infamous of Tupac incidents, it went down on November 30, 1994. That night Pac was on his way to record a song with Lil Shawn in Quad Studios. However, instead he was ambushed by assailants and was robbed and shot five times. Pac swore he was set up, naming people like Sean “Diddy” Combs, the Notorious BIG and James “Jimmy Henchmen” Rosemond responsible. Just this year, an inmate came forward to say that Pac was indeed set up.

Wheel of Misfortune


After sustaining five bullet wounds (two in the head, two in the groin, one in the arm and thigh), ‘Pac checked himself out of Bellevue Hospital only three hours after surgery. The following day, a wheelchair-bound ‘Pac showed up to a court hearing for his sexual assault case and was found guilty of three counts of molestation. He was found not guilty on six other counts, including sodomy. 'Pac was sentenced to one and a half to four and half years in prison.

Straight Spittin'


‘Pac gave paparazzis the photo opp of a lifetime when he walked out of a courtroom. Sporting a Detroit Red Wings hockey jersey and a red bandana, ‘Pac walked out of the courthouse and spat at every reporter in sight. “That’s my new style,” he said before hopping in the passenger seat of a minivan. “Have a good summer, biatch,” he added as the vehicle took off.

'Pac Gets Risqué


Tupac may have taken his sex symbol status a bit too seriously during a 1996 photoshoot with famed photographer David LaChapelle. Most hardcore rappers would lose their cred after posing in a bathtub filled with bubbles, or with a Mr.T-like amount of chains covering their crotch. 'Pac made it work.

'Pac Rides on the East Coast

Hit 'Em Up

Though Tupac and Biggie Smalls's relationship had been strained since the Death Row rapper suspected Big and Puffy of being involved in his '94 shooting at Quad Studios, things took a turn for the worse when 'Pac released "Hit 'Em Up"—the B-side to his smash single, "How Do U Want It” on June 4, 1996. “First off, fuck your bitch and the clique you claim/West Side when we ride come equipped with game/You claim to be a player but I fucked your wife/We bust on Bad Boys, niggas fuck for life,” ‘Pac spits, hinting that he had an affair with Faith Evans, on the scathing record’s first four bars. ‘Pac also dissed Puffy, Lil’ Kim, Lil Cease, Junior M.A.F.I.A., Mobb Deep, Chino XL on the song and warned that any MC from New York could get it. The inflammatory record added fuel to the East Coast/West Coast feud and prompted responses from several NY MCs. To date, “Hit ‘Em Up” is considered one of the most vicious diss records of all time.

'Pac 2-Pieces Orlando in Las Vegas

'Pac 2-Pieces Orlando in Las Vegas 96

What was a celebratory night turned violent in a flash. It was September 7, 1996 at the MGM Grand where 'Pac and his entourage had just seen the Mike Tyson vs. Bruce Seldon fight. While leaving, someone in the crew spotted Orlando “Baby Lane” Anderson, a member of the Southside Crips who was persona non grata with Suge Knight. Needless to say, 'Pac, Suge and company proceeded to stomp Anderson out and the entire incident was caught on tape. 'Pac would be shot later on that night, succumbing to his wounds six days later.

The Craziest Shit 'Pac Ever Wrote


Tupac never believed in subliminals. On "Against All Odds," the closing track to his first posthumous LP, The Don Killuminati: The 7 Day Theory. The ferocious rapper added Nas and De La Soul to his growing list of enemies in addition to firing more shots at Puffy and Mobb Deep. As if calling out New York’s finest wasn't enough, 'Pac fearlessly (or foolishly) called reputed Brooklyn gangsta Haitian Jack a snitch, accused former friend Jimmy Henchman of setting up the Quad shooting and threatened Walter “King Tut” Johnson, who was once charged in the Quad shooting. ‘Pac clearly knew he was crossing the line. “Probably murdered for the shit that I said,” he rhymes towards the end of the song. 'Pac was shot on September 7, 1996 and died six days later—roughly two months a half before "Against All Odds" was released.