Our Ten’s List: Best Movies Featuring Hip Hop Stars

Our Ten’s List:  Top Ten Movies Featuring Hip Hop Stars

The early 90’s was the heyday of two musical movements:  Rap and the music video.  Hip Hop as a genre thrived on pushing boundaries, and this naturally led to artists playing with the medium of music videos, often creating works that were closer to mini-movies than to traditional music videos.  Several performers made the jump from the small screen to the box office directly, starring in major motion pictures.  Here we’ve collected ten of the best films featuring rappers turned thespians.

10.  Training Day (2001)

Featuring:  Dr. Dre, Snoop Dogg, Macy Gray

10 trainingJake is a rookie cop who is assigned to shadow Alonzo, a decorated narcotics detective.  It turns out to be a day in hell for Jake as he witnesses Alonzo break every rule in the book in order to catch criminals.  Smoking PCP, raiding drug stashes, pistol whipping witnesses and stealing millions of dollars in drug money from very angry gang members is all part of the routine for Alonzo, who may in fact be the biggest criminal in the city, despite his sterling reputation with his co-workers.

Dre and Snoop’s roles in this film are marginal, but they do add some much needed levity to this award winning film which is almost completely morbid.  Denzel Washington plays against his good-guy type as the scheming Alonzo, and reminds us why he is one of the most versatile actors currently in the business.

Dre, seen here injecting levity into a project.
Dre, seen here injecting levity into a project.

9.  House Party (1990)

Featuring:  Kid ‘n Play

Shhh, don't mention House Party 2...or House Party 3!
Shhh, don’t mention House Party 2…or House Party 3!

Most of the films on this list are decidedly grim, taking an unflinching look at gang life.  House Party is refreshing break from gun battles and police brutality.  Two high school friends are attempting to end their school career with a bang by throwing the biggest house party the city has ever seen.  From the get go, things go hilariously wrong.  After a run in with a school bully, Kid gets grounded, and has to sneak out of his house just to make it to his own party.  The night only gets worse as he tries to cross town in time to make an appearance at Play’s house, and hopefully get the attention of Syndey, the prettiest girl in school.

House Party is lighthearted fun all through, and in retrospect, it feels like a movie length episode of The Fresh Prince of Bel Air.  Which reminds me, no Will Smith on this list until he stops trying to make us watch his horrible children.

Fuck you. Where's Jazzy Jeff?
Fuck you. Where’s Jazzy Jeff?

8.  Romeo Must Die (2000)

Featuring:  DMX, Aaliyah

Rappers and Kung Fu are like peas and carrots.  And just like peas and carrots, they can be pretty awful if not handled correctly.  I’m looking at you, The Rizza.  DMX has dabbled more than a few times in making action movies, to mixed results.  Exit Wounds was enjoyable if you mentally subtract Steven Seagal from the film.  Death Toll...had Lou Daimond Phillips in it…so that’s a thing.  Oh hey, who can forget Lockjaw: Rise of the Kulev Serpent?  Anyone else see that picture?  No?


10 romeoWell, DMX did manage to make two good films, both starring alongside Jet Li.  The best of those collaborations was Romeo Must Die, an interesting take on Shakespeare’s famous feuding families, where two rival gangs vie for control of the city, mostly by way of spectacular martial arts fights.  Jet Li is the good son of a Hong Kong Triad family which has set its eyes on buying up real estate in order to cash in on development deals.  They run afoul of the scion of a powerful gang who has interests in the neighborhood, and who is trying to clean up his criminal act by also using real estate to get out of the game.  When Jet Li’s brother is murdered after trying to work out a nonviolent deal, it looks like a gang war is inevitable…and that factions inside both family may be stoking the fires for personal gain.

Oh yeah, X gon give it to ya.
Oh yeah, X gon’ give it to ya.

7.  Hustle and Flo (2005)

Featuring:  Ludacris, Juicy J, DJ Paul, Haystack, Al Kapone, I-20

10 hustleDJay is a pimp and drug dealer who dreams of getting out of the thug life.  When he comes across an old friend who is working in the recording industry, he fools around with making a hip-hop track, and turns out to have a solid talent for rapping.  He experiences minor success getting his tracks played locally, but needs a boost if he’s going to be able to quit his day job of pimping.  When a notorious rapper and his posse come to town, DJay thinks he can make it big if he can just get noticed by a national act.  His dream becomes a nightmare, as his hero turns out to be less than enthusiastic about helping a fledgling artist.

Ludacris, not the nurturing type, apparently.
Ludacris, not the nurturing type, apparently.

The deft touch of John Singleton keeps Hustle and Flo from becoming a farce.  The stereotypes in this movie verge on blaxploitation levels…the main character is a pimp who is literally named DJ.  This film could have ended very badly for all involved, but the earnest nature of the drama carries it over the rapids, and the final act is a sober look at the nature of struggling to make it in the music business, especially when that avenue is often the only means of escape for many urban kids trying to avoid crime and poverty.

6.  Be Kind, Rewind (2008)

Featuring:  Mos Def, MC Paul Barman

10 rewindBe Kind, Rewind is a quirky comedy from the creator of Eternal Sunshine of the Spotless Mind.  Mos Def plays Mike, a hard working clerk at a VHS rental store who becomes an accidental star.  He is friends with a walking disaster named Jerry (Jack Black) who accidentally erases all of the magnetic tapes after nearly electrocuting himself.   In order to keep his job, Mike and Jerry try to re-record all of the movies, using a camcorder and their own incomplete memories of the films.  Their efforts become more popular than the original movies, with people coming from far and wide to watch their new “sweded” versions of iconic movies like Ghostbusters, Robo Cop, and Rush Hour 2.  The pair hope that new films will revitalize the failing business in time to avoid the city’s plan to demolish the building.

Be Kind, Rewind is one of those comedies that manages to be ground breaking without being ludicrous.  Jack Black, usually a manic tornado of insufferable energy, is lovable and low-key as a mentally confused Jerry, and Mos Def’s Mike is charming and engaging.  Supported by the talents of Danny Glover, Sigourney Weaver, and Mia Farrow, this bizarre film is every bit as wonderful as the “sweded” flicks that Mike and Jerry pass off as classics.

Better than the reboot...
Better than the reboot…

5.  Juice (1992)

Featuring:  Tupac Shakur, Queen Latifah

10 juiceTupac Shakur had a sterling resume of films under his belt before his tragic and untimely passing.  The best of these was Juice, a gritty and violent look at four young men trying to survive in Harlem.  Shakur plays Bishop, the charismatic and deadly center of the group who plots to gain fame and wealth through a series of robberies.  His friends are reluctant, but Bishop uses charm and force in order to get his way.  When the robberies go awry and people wind up dead, the four youths watch their friendship shatter, and find themselves in the cross-hairs of a desperate Bishop who is willing to go to any lengths to get rich and avoid jail time.

Juice is powerful and mesmerizing, due in large part to Shakur’s screen presence as Bishop.  The film feels like a Coen Brother’s piece, where normal people are confronted with a devil’s bargain, and end up becoming devils themselves in order to avoid the consequences of their actions.

4.  Friday (1995)

Featuring:  Ice Cube, DJ Pooh, WC

10 fridayBefore Ice Cube became the center of a movie empire, he made Friday, a surreal slice-of-life comedy centered around two likable losers who are having a rough day.  Cube plays Craig, a hard working but bitter young man living in South Central.  On the day in question, he gets fired from his lousy job for a bullshit offense, gets cussed out by his dad, runs afoul of the local bully Deebo, and gets pulled into a botched drug deal by his perpetually stoned friend, Smokey (Chris Tucker, in one of the few times his shrill style is actually funny.)  Craig and Smokey experience every “typical” aspect of inner city life…all in one very atypical day.

Cube's reaction after reading the script for XXX: State of the Union.
Cube’s reaction after reading the script for XXX: State of the Union.

Friday is pretty much a classic, and established Ice Cube as a bankable actor.  He’d played hard-assed characters before, essentially using the same persona as his rap career, but Friday showed that he had the chops for comedy as well.  Three Friday movies, four Barber Shop movies, and who knows how many Are We There Yets later, Ice Cube has made himself a neat fortune playing upon the “tough guy having a bad day” comedy routine he perfected in Friday.

3.  New Jack City (1991)

Featuring:  Ice T, Flavor Flav

10 new jackNew Jack City attempted to do for crack dealers what Scar Face did for Colombian cocaine traffickers.  Wesley Snipes is a ruthless drug lord in New York with a death grip on nearly every lucrative crime in the boroughs.  Ice T plays an undercover cop from the streets who goes undercover in an attempt to break up the burgeoning crack rock empire.  While the film has this police drama as a skeleton, the real meat of the movie is Snipes as the gorgeously sadistic Nino.  Great dialogue and excellent work by Snipes makes Nino a villain that is great fun to watch.  The message of crack’s danger gets blurred by the excitement and glamour of gang life, but it manages to be so relentlessly entertaining, you forgive the film for turning slinging rock into a sexy profession.

2.  Menace II Society (1993)

Featuring:  MC Eiht

10 menaceOur top two picks feature cautionary tales about the struggles of inner city life and the harsh conditions that drive young people into criminal life styles.  Menace II Society tells the story of a trio of friends, Caine, O Dog and A-Wax, who get caught up in a life of crime and poverty in South Central.  Caine is the child of violence and drug use, with his father a drug dealer who was murdered and his mother was an addict.  He is raised by his grandparents, but his ties to the street keep him from rising above his surroundings.  Despite a relationship with a girl named Ronnie who offers to take him out of LA, Caine can’t seem to break his ties and be free.  He follows the lead of his friends and ends up participating in robberies, murders, carjackings, and other criminal offenses.  When his grandparents kick him out for being a thug, Caine has a change of heart…but it may be too late for him to escape his past.

Cradle to the grave.
Cradle to the grave.

Menace is one of those films that leaves you physically shaken after watching it.  The violence and depravity are not glamorized, and the life of a criminal is not presented as sexy or exciting.  Every crime feels like another shovel of dirt on the casket of Caine and his friends, and you watch helplessly as a terrible environment slowly but surely creates a “monster” out of these young men.  It’s a harrowing and necessary film.

1.  Boys n Tha Hood (1991)

Featuring:  Ice Cube

10 boysBoys n Tha Hood is John Singleton’s magnum opus.  Like Menace II Society, it takes an unflinching look at inner city crime and the cycle of violence it creates.  Unlike Menace, Boys n Tha Hood leaves a small glimmer of hope for audiences to clutch at, despite much of the film being dark and foreboding.

Tre (Cuba Gooding Jr.) is a smart young man who is losing his way in the projects.  His mother sends him to live with his estranged father, hoping that a male influence will counter-act the allure of gang life.  Tre’s childhood friend, Doughboy (Ice Cube,) is a member of the Crips, and his lifestyle is starting to rub off on Tre.  Several of their mutual friends are shot or killed in the height of the Bloods and Crips rivalry, and Doughboy is intent on seeking revenge.  Tre is pulled by his desire to escape the city and follow his dreams of attending college, but also by his loyalty to Doughboy.  When another friend, who likewise had a strong chance of making it out of the city on a scholarship, is killed by gang warfare, the two halves of Tre’s life are torn apart.  Now he has to decide which life he wants to lead, knowing that the choice will force him to abandon either his friends or his future.

Go ahead, make an "Are We There Yet?" joke. I dare you.
Go ahead, make an “Are We There Yet?” joke. I dare you.

Singleton has dominated this genre, alongside Spike Lee, for good reason.  His characters are solid and multifaceted, his narratives are gripping and remind one of a Greek tragedy, and his films all feel grounded in their settings.  Boys n Tha Hood is his best piece, and showed Ice Cube as a rising star capable of carrying a dramatic lead.

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