Lord Flacko. Jodye II. A$AP Rocky now has a new pseudonym he can add to the list: Yung Felon – the name of his character in upcoming crime thriller High and Low directed by Spike Lee. 

Spotted by paparazzi on the High and Low set last week, A$AP Rocky joins already-announced cast members Ice Spice and frequent Spike Lee collaborator Denzel Washington in a remake of Akira Kurosawa’s 1963 film of the same name. Kurosawa’s original follows businessman Kingo Gondo as he deals with the attempted kidnapping of his son, endangering a pivotal moment in his career.

This will not be A$AP’s first film foray, previously portraying drug dealer Dom in Dope and even cameoing as himself in Zoolander 2. Given the genre’s rapid rise to the mainstream in the early 90s, and rappers’ evident ability to deliver a line, hip hop and the big screen go way back, contributing not only to the rags to riches narrative that rap is known for, but also a wider diversification of cinema-at-large and the stories it aims to tell.

In light of this rich history, we pick ten of our favourite moments where rappers turn raconteur...

EMINEM IN 8 MILE

Right, shall we get it out of the way? Let’s get it out of the way. Eminem’s appearance in heavily fictionalised biopic 8 Mile is the elephant in the room – or, rather, the B Rabbit. Responsible for making every rap fan’s mom exclaim “I get it now!”, Em in 8 Mile in many ways set the benchmark for what a hip-hop-Hollywood crossover could achieve.

ICE T IN NEW JACK CITY

Long before 8 Mile introduced Middle America to mom’s spaghetti, Ice T was pioneering hip hop’s flirtation with headlines in tracks like 1992 release “Cop Killer”. At the same time, T was also extending the genre’s horizons when he became the first rapper to secure a leading role in a Hollywood production, ironically playing cop Scotty Appleton in New Jack City. With a stellar soundtrack drawing on hip hop, R&B and new jack swing, it’s hard to underestimate the film’s cultural impact, being endlessly referenced in rap lyrics to come and also providing the namesake for Birdman’s Cash Money Records.

TUPAC IN JUICE

The following year, Tupac made his debut on the big screen with Juice, one of the single best performances by a hip-hop artist in film to date. The lyrical Makavelli’s gangster background formed a match made in heaven for protagonist Bishop’s Machiavellian power plays, humanising his descent from innocent child to violent criminal.

MOS DEF IN THE WOODSMAN

Where Tupac, Em and even Ice T’s portrayals stay relatively close to their rap personas, Mos Def is particularly notable for breaching hip-hop typecasting in his film appearances. His role as Ford Prefect in Hitchhiker’s Guide to the Galaxy is about as far from hip-hop as you can get, but it was his portrayal of Sgt Lucas in The Woodsman that saw him awarded best actor at the Black Reel awards. The film features a haunting monologue from Def’s Lucas in the closing act, calling out convicted child molester Walter, played by Kevin Bacon. 

LAURYN HILL IN SISTER ACT 2: BACK IN THE HABIT

Way before the Fugees and The Miseducation of Lauryn Hill, Lauryn was being pretty well educated by Whoopi Goldberg in Sister Act 2. The film was a breakout moment for hip hop’s first lady, seeing her perform “His Eye on the Sparrow” and “Joyful, Joyful” on-screen. According to Atlantic Records exec Jerry Greenberg, she received an offer of a record deal by Michael Jackson for her performance in the film, which Hill allegedly turned down due to already working on The Fugees’ debut album Blunted on Reality.

DMX AND NAS IN BELLY

If New Jack City was hip hop getting its foot in the door, Belly blew its hinges off. Renowned music video director Hyper Williams’ only full length directorial credit, the film boasts an all-star hip-hop and R&B line-up, spanning Nas, DMX, Method Man, and T-Boz. Going on to direct the iconic music videos for “Gold Digger” and “All The Lights” later in his career, Williams’ eye for style and colour really shine through here, creating one of the best opening scenes in film history.

EVERYONE IN TOP BOY

Yes. That’s right. Everyone. With a cast that draws so heavily on the UK’s rap and grime lineage, it’s a bigger challenge pointing to someone in Top Boy that wasn’t spitting bars on pirate radio in the early 2000s. Over its five seasons, the series has seen appearances from Dave, Asher D, Little Simz, Bashy, Nolay, and Scorcher, to name a few, though it was Kano’s deeply emotive portrayal of tragic villain Sully that proved the biggest breakout star. The prince of grime has since said that he has “no interest in the industry of acting”. Big L.

AWKWAFINA IN SHANG CHI AND THE LEGEND OF THE TEN RINGS

The MCU might not be the first thing that comes to mind when you think of hip hop, but Shang Chi holds a very specific significance. With a soundtrack album produced entirely by Asian-American hip-hop and R&B label 88rising, and leading role filled by Asian-American rapper-actress Awkwafina (Nora Lum), the film notably platformed emerging Asian-American perspectives in media. Awkwafina first hit the public consciousness with her 2012 “My Vag” remix of Mickey Avalon’s “My Dick (Tribute to Nate)”, and subsequently appeared in Asian-American hip-hop documentary Bad Rap alongside forerunner Dumbfoundead, which highlights their struggle to be taken seriously in the creative industries. Meanwhile, 88rising self-identifies as “the Disney of Asian hip hop” and is credited for breaking stars Rich Brian, Joji and Higher Brothers, some of the East’s biggest names to date. With all-star Asian and Asian-American backing, Shang Chi managed to tie together various threads to deliver a superhero movie that does justice to the cultural lineage it is built upon.

METHOD MAN AND REDMAN IN HOW HIGH

Method Man and Redman (of loose Wu-Tang association) in an early 2000s stoner comedy about smoking the ashes of smart people to get into Harvard? Brilliant. How High’s 25 per cent approval rating on Rotten Tomatoes only serves to exemplify its execution of the mission. As low-hanging as its plot is, the film is also significant for moving away from the typical rapper typecasting in cinema – portraying the duo as lovable rogues, as opposed to the gangster-adjacent roles that stars had previously been confined to.

AFRO SAMURAI 

Whilst not directly featuring a rapper (unless you count Samuel L Jackson), Afro Samurai is about as hip-hop as you can get. Based on the dōjinshi (self-published) manga by Takashi Okazaki, the Afro Samurai anime series and subsequent film were built around a “creative collaboration” between Wu-Tang member and series soundtrack producer RZA, Samuel L Jackson, Okazaki and director Gonzo. More than anything, the series stands as a celebration of the extensive reciprocal love affair between hip-hop, anime, and Eastern culture, stretching all the way back to Wu Tang’s formative martial arts philosophy in the 90s.