Hollywood has a long and problematic history with race. From the blackface prevalent in comedies and cartoons, to the stereotypical roles for even the most accomplished Black actors, Tinseltown has never been as progressive as it wants to believe--especially not when it comes to race. In 1987, a young filmmaker named Robert Townsend took aim at Hollywood in his very first feature film. Townsend would deliver the classic comedy Hollywood Shuffle, a smart and skewering look at what it meant to be Black in Hollywood in the 1980s. As should be expected, much of the movie's biting wit and social commentary still hold true today.

Long before #OscarsSoWhite or Spike Lee's Bamboozled, up-and-coming filmmaker and actor/comedian Townsend teamed with his friend, fellow then-unknown funnyman Keenan Ivory Wayans, and hammered out a script that took aim at everything--including racist stereotypes, selfish Black stars and Hollywood's love affair with the then-red hot Eddie Murphy. Written and produced independently, they funded the movie themselves using credit cards. Townsend was committed, having appeared in a few films previously, he decided his directorial debut would satire the experience of being a young Black actor.

"This movie came out of pain and frustration," Townsend told the New York Times in 1987. "I don't want to be bitter, but I had to get it out of my gut. If you look at the movie, it's a showcase for a lot of black talent. It's not just a minstrel show. We're talented comedians. If you look at one dimension of this movie, you miss the whole show."

It's been thirty years since Robert Townsend released his classic comedy. We ranked our five favorite scenes from Hollywood Shuffle. 

 

  • 5

    "NAACP Uncle Tom protest"

    Feeling the pressure of the kinds of roles that he's being offered, Bobby Taylor (Townsend) ponders what it would be like to become a major star--but a sell-out. A mob of angry protestors gather outside of his house, as various personalities (including Paul Mooney as President of the Hollywood branch of the NAACP) give hilarious commentary on his downfall.

  • 4

    "Winky Dinky Dog!"

    Bobby Taylor has to make ends meet by working at Winky Dinky Dog, with two inept coworkers and an overbearing boss, Mr. Jones (played by the always-funny John Witherspoon.) When Bobby complains about not being able to use his creativity, Mr. Jones explains that he's creative at Winky Dinky Dog, and rattles off his unique creations--which include the Winky Dinky Ho Cake.

  • 3

    "Gimme my activator, man!"

    Fantasizing about life as a Private Eye, Bobby confronts the tough guy Jheri Curl. But to get him to talk about the day Cookiehead Jenkins was killed, Bobby has to take the thing Jheri Curl loves the most and hold it hostage. Demanding to know the details, Bobby questions Jheri Curl (played by Keenan Ivory Wayans) as the would-be tough guy tearfully pleads for his activator.

  • 2

    "Eddie Murphy"

    It takes some nerve to spoof the biggest Black actor in Hollywood, but Townsend and Co. did just that with this hilarious parody of narrow-minded casting calls. While having a nightmare about an audition, Townsend's Bobby dreams of being surrounded by an army of Eddie Murphy wannabes. (The jokes are even funnier if you know that Saturday Night Live execs passed on Townsend in favor of Murphy back in 1981.)

  • 1

    "Black Acting School"

    The movie's defining moment, this pointedly funny sketch features Townsend as a former house slave fleeing the "Massa" who reveals himself to actually be a classically trained actor who runs a very specified school for Black thespians. It helps them learn how to effectively play slaves, pimps and addicts. Burn Hollywood, burn.