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The recent release of the official trailer for the upcoming Jimi Hendrix biopic All Is By My Side, starring Andre 3000, reminds us of all the glorious and often hilarious moments in which the world of hip-hop collided with the world of film.

Speaking generally, the meeting of these two worlds hasn’t always gone smoothly, though there have been many gems. Either way, it looks like rappers aren’t leaving Hollywood anytime soon. Perhaps a glance at the lessons of the past will help give context to Andre 3000’s highly anticipated performance. And so, here are the ten on-screen performances by rappers that impressed us most. We’ll have to wait and see whether or not Andre 3000 makes it onto the list.

1. Eminem in 8 Mile (2002)

Who could forget Rabbit throwing up his mom’s spaghetti in the bathroom in the opening sequence before his rap battle? Slim’s performance inspired a whole generation of underdog rappers to step up and own the Papa Doc’s in their own lives. He also won an Academy Award for Best Original Song with his single “Lose Yourself.” Hard to beat that.

2. Queen Latifah in Chicago (2002)

Few ’90s babies even know that Queen Latifah had bars back in the day. Most will recognize her from trashy comedies like Bringing Down The House (2003). But her best on-screen performance by far was as Matron “Mama” Morton in the musical-turned-to-film, Chicago. She received an Academy Award nomination for Best Supporting Actress. Sadly, Mama hasn’t been that good to us since.

3. 2Pac in Juice (1992)

Pac’s career as a rapper was just taking off when he took on the role of Bishop in the movie Juice. Though Omar Epps starred as the film’s noble protagonist, 2Pac’s good-kid-gone-haywire ultimately stole the show, and made Juice into an outstanding urban tragedy.

4. Ludacris in Crash (2004)

Who knew Luda had those acting skills? The Grammy-Winning Atlanta rapper surprised everyone with his performance in Crash, portraying an angry, paranoid car-jacker who eventually changes his ways. He received a nomination for Outstanding Supporting Actor in a Motion Picture at the NAACP Image Awards. Hard to believe it was the same Ludacris acting in Fred Claus.

5. Will Smith in Ali (2001)

Yet another actor whose rapping career is pretty much totally unknown to ’90s babies. Smith’s portrayal of the legendary boxer, Muhammad Ali, in this 2001 biopic earned him an Academy Award nomination for Best Actor. For those who knew him best for his TV Series The Fresh Prince of Bel-Air, and for cool but mostly comedic roles in movies like Men In Black and Independence Day, it was a thrilling experience to see him take on a more serious role.

6. Ice Cube in Boyz N The Hood (1991)

Before starring in fluffy family-friendly comedies like Are We There Yet?, Cube used to be as gangsta on-screen as he was on record. The NWA veteran rapper’s first appearance on film was a total success. Though his acting skills weren’t really incredible, his role as “Doughboy” gave cohesion to the classic, heart-wrenching ‘growing up in the hood’-drama.

7. Ice-T in New Jack City (1991)

Of course, it would be Wesley Snipes’ character, the ruthless drug-kingpin, Nino Brown, that would go on to catch countless references in countless mafioso-rap songs. Ice-T was the only actual rapper in the movie (except for a brief appearance from Flavor Flav). And though most know at least one Nino monologue word for word, we were all rooting for Detective Appleton in the final fight between him and Nino. For better or worse, the film remains an integral part of hip-hop culture.

8. 50 Cent in All Things Fall Apart (2011)

Though the film’s box office success pales in comparison to his kind-of-biopic, crime-drama Get Rich Or Die Tryin’ (2005), 50 Cent’s dedication to his role in All Things Fall Apart was truly something to behold. The Queens rapper lost 54 pounds in order to play his role as an ex-football player suffering from terminal cancer. The performance did not even come close to meriting an Oscar, but certainly an A+ for effort at the very least.

9. Run-DMC in Krush Groove (1985)

The long-forgotten Russell Simmons-produced movie is a treasure trove of old school hip-hop nostalgia, starring The Fat Boys, Beastie Boys, LL Cool J, and most importantly, Run-DMC. This is another movie that made the list, not due to a particularly stellar acting performance, but because it is an iconic hip-hop movie about the conception of one of hip-hop’s most important labels, Def Jam Records. Run-DMC brought charisma and coolness to the table and they’re one of the best rap groups of all time. End of story.

10. Mos Def  in Something The Lord Made (2004)

Ali was a jump for Will Smith from his usual roles– though, Ali’s charisma and braggadocio attitude still made for a fairly safe role for an ex-rapper to play. Now, Mos Def playing a pioneering heart surgeon– that was miles away from the world of hip-hop. Nevertheless, Yasiin Bey proved his worth as an actor, masterfully taking on the role of Doctor Vivien Thomas. Though the movie never made it to the big screen, its premiere on TV was still relatively successful, winning 9 Emmy Awards.

Honorable Mention:

#11. Ice Cube in Friday (1995)

Once again, nothing particularly amazing about this movie. It is simply a treasure trove of hilarious catch phrases that will be used in rap lyrics and in everyday conversation forever. Most notably, perhaps…

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