BySean Gallen, writer at
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Sean Gallen

This year marked the 20th anniversary of the untimely passing of a hip-hop legend, Tupac Shakur. The rapper was shot down by gang members at the ripe age of 25 but he left behind a huge legacy of seminal albums that helped push hip-hop to the mainstream. This anniversary is made a little less somber by the news of two upcoming biopics about the rapper's life: one about his final days, All Eyez On Me, and another, Labyrinth, about the officer responsible for tracking down whoever killed Tupac.

Check out the trailer for All Eyez on Me below:

Fans and filmmakers alike focus so much on Tupac's music because it was so provocative and influential, his acting career is often overlooked; but the rapper was prolific in '90s cinema and dedicated himself to depicting black life in America in the films he chose. We take a look back at some of his finest performances and moments in film.

1. Juice - The Iconic Monologue

Juice is usually heralded as Tupac's finest performance because of his fiery attitude but also because the script was bursting with quotable dialogue that would be sampled by other rappers, re-hashed, printed on t-shirts and repeated by rebellious teenagers everywhere. The story follows four young teens in a troubled neighborhood who go down the dark and dangerous path of crime when they get their hands on a pistol. Tupac brought the violent and anarchistic energy from his music to this performance which is on display in this iconic monologue as he threatens his former friend.

2. Above The Rim - Tupac The Ruthless Gangster

Shakur was often cast as the villain who threatened the safety of all around him. Early on in his career he played either the gangster or the drug dealer who looked out only for himself. Tupac was raised by two black nationalists and was brought up to be aware and critical of how black people are perceived in America. His critical thinking would have an effect on these gangster roles as the characters he chose were always foiled by the system or their own violent behavior. In Above the Rim he plays Birdie, the ruthless drug dealer who terrorizes the neighborhood into submission. In this scene, we see the lengths he's willing to go to protect his reputation.

3. Poetic Justice - Janet And Tupac's Undeniable Chemistry

Poetic Justice pitted two huge personalities in Janet Jackson and Tupac against each other and watched the sparks fly. The duo are constantly clashing with each other but eventually open up to each other when they are forced to travel across the country together. The chemistry between the two is irresistible as they go back and forth and the dialogue is scintillating but also written in a distinctly black voice (the poetry Janet recites was written by Maya Angelou herself). In this scene, we see Tupac like never before, as a ne'er do well postman down on his luck. He makes the mistake of trying his luck with Justice (Janet) who shoots him down in the most beautiful fashion.

4. Gridlock'd - Tim Roth And Tupac Have No Respect

Tupac was always interested in showing the nitty-gritty details of the people forgotten by society: drug dealers, gangsters, drug users. In Gridlock'd he teamed up with Tim Roth and Thandie Newton to tell the story of three junkies drifting around Detroit with only each other to rely on. Many still question his acting ability to this day, but seeing him alongside Tim Roth, he definitely holds his own bringing this harrowing story to life. In this scene, the two strung-out heroin users have been in the police station all day, shifted from department to department. Spoon (Shakur) shows his total lack of respect for the law when the black officer tries to talk down to him.

5. Gang Related - Roles Reversed

Gang Related is another standard buddy cop drama of the ilk that was pervasive in the '90s, but what made it stand out was Tupac's performance on the other end of the long arm of the law. The story follows an odd couple, Frank Divinci (James Belushi), a shaggy, crooked cop looking to make some money to retire on, and Jake Rodriguez (Tupac), who gullibly follows him down the dark path of corruption. The partners begin dabbling in drug trafficking and are forced to gun down a local dealer only to find out he was an undercover DEA agent. Tupac shows his versatility by abandoning the gangster role to play the role of a young police office who started with the best intentions but is inevitably corrupted by the sleazy Divinci who seduces him with the promise of easy money.

What's your favorite Tupac moment in film?


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