It's still hard to believe how much Tupac Shakur achieved in just a few short years. Not only was the late musician one of Hip Hop’s most magnetic voices in the ‘90s, but he was also turning into one of the era’s most compelling actors. His presence carried the same energy on screen as it did on the mic, and the roles he chose, whether it be lovers, addicts, or even detectives, showed a range that was rare for a rapper-turned-actor at the time.

While plenty of musicians have made the jump to Hollywood — Will Smith, Queen Latifah and so on — there are few who did it like Shakur. Juice cemented him as a leading man almost instantly, while Poetic Justice paired him with Janet Jackson in a romance that critics and fans alike still talk about decades after its release. However, it’s far from the only role the “Keep Ya Head Up” rapper has taken on and, frankly, crushed.

So, in celebration of all the times he took a break from music to show a different side of his artistry on the big (and small) screen, here’s a look back at Shakur’s best acting roles.

1. Juice

Just a year after releasing his debut album, 2Pacalypse Now, Shakur reached what many would say is his peak as an actor with Juice. He starred as Bishop, a Harlem teen whose thirst for respect rapidly descends into violence that costs the lives of the very people closest to him. There’s a reason Tupac’s face was front-and-center on every movie poster. He’s magnetic, chilling, and at his absolute best in the Ernest R. Dickerson-directed effort.

2. Poetic Justice

If not Juice, then Poetic Justice is definitely next in line for Shakur’s best acting performance. The film offers everything you could ask for in a ’90s romance: Janet Jackson as a hairstylist-turned-poet coping with the death of her boyfriend, Regina King talking trash from the back seat, and Tupac playing opposite all of it. With Lucky, he portrayed a mail carrier whose patience gradually breaks through Justice’s grief. He argues, jokes, and flirts his way through their scenic drive to Oakland, leaving plenty of space for Janet to shine as both lead and poet.

Believe it or not, Ice Cube also had the chance to play Lucky. “I turned down the Tupac role in Poetic Justice,” he told Big Boy. “The problem was, me playing Tupac, I don’t think I’d kick my homeboy out the car for a girl I just met when we got to Oakland. I didn’t think that was cool.”

3. Above the Rim

Above the Rim can be appreciated either as a basketball movie or a cautionary tale about who you trust when you’re one step away from making it. It’s a Tupac film, sports flick, crime drama, and a tragic character study all at once. The late rapper played Birdie, a local dealer, and Shep’s younger but nowhere near as wise brother. Of course, Shakur also contributed the beloved “Pain” to the movie’s tracklist.

4. Gridlock'd

Tupac is at his best when he’s playing characters who are a little burned out but still trying. In Gridlock’d, he plays Stretch, a heroin addict who decides — mostly by accident — to get clean with his best friend, played by Tim Roth. However, it turns out the system doesn’t make it simple. He’s just trying to make it through the day, people.

“This movie is really about friendship and what unconditional friendship means,” Tupac said about the part. “I did it basically because it was funny, and I’ve never really got to be funny.”

5. Bullet

Tupac, sadly, died a year before Bullet hit theaters, making it his first posthumous release. He’s introduced as Tank, a drug dealer who spent much of the film trying to settle the score with Mickey Rourke’s recently paroled Butch. Considering Butch was the reason Tank wears an eye patch, his anger — and eventual fate — was arguably justified. The “Hit ‘Em Up” rapper was great at playing villains, and Bullet definitely gave him that chance.

6. “A Different World”

The late artist was a great fit as Piccolo, Lena’s charming and slightly problematic ex in “A Different World.” He only appeared in one episode, though the way he and Jada Pinkett Smith play off each other is great, to say the least. It’s a shame they didn’t explore his character more.

“I didn’t have to lobby to get him on. I think it was a suggestion, and everyone was like, ‘Yes!’ We kind of did that for each other. We were always trying to look for opportunities to work together,” Jada Pinkett Smith explained to Entertainment Weekly, noting that Tupac was the reason she landed a role in Menace II Society. She added, “We were always looking out for each other.”

7. Gang Related

Shakur entered Gang Related like he’s been living in its crooked world for years. As Detective Rodriguez, he played a corrupt cop trying to cover up a murder he helped commit. Yes, the rapper’s character and Detective Divinci (James Belushi) were in far deeper than they could ever handle, which is probably why their attempts to fix things just make it worse. The movie goes through all that drama just to have Shakur’s character murdered over a gambling debt, of all things.

8. Nothing But Trouble

Everyone has to start somewhere. For Shakur, that meant a minutes-long cameo in Nothing But Trouble, where he appeared with Digital Underground during a courtroom performance of “Same Song.” There’s nothing particularly groundbreaking about the role itself, but it’s technically his first movie appearance.

9. “Drexell's Class”

Tupac isn’t in much of the quickly canceled “Drexell’s Class,” and for that, he can probably be grateful. The show only lasted one season, with the musician making his introduction with Digital Underground. At least he had more fun than the adults paid to stick around.