Every Dave Chappelle Movie, Ranked

Ranker Film
Updated August 1, 2023 688 votes 235 voters 53.2K views
Over 200 Ranker voters have come together to rank this list of Every Dave Chappelle Movie, Ranked
Voting Rules
Vote for your favorite Dave Chappelle movies, regardless of critic reviews or how big the role was.

More than 200 movie fans have come together to cast their votes for the best Dave Chappelle movies. From his iconic standup specials to his hilarious skits on Chappelle's Show, Dave Chappelle has been making us laugh for decades.

His signature brand of humor, which often combines edgy satire with insightful social commentary, has earned him legions of fans all around the world. Among these fans, there is no shortage of debate about which of Dave's movies is truly the best. Some may argue that it's his classic Half Baked and You've Got Mail, while others might point to cult classics such as The Nutty Professor as proof that he can do just about anything in front of a camera.

No matter your opinion on the subject, one thing is certain: this list showcases some of Chappelle’s greatest hits and will help you decide what titles should be at the top your watchlist next time you want a good laugh. So make sure to check out our rankings and vote up your favorite Dave Chappelle films today.

Ranked by
  • Half Baked
    1

    Half Baked

    Dave Chappelle, Guillermo Díaz, Jim Breuer
    74 votes
    • Released: 1998
    • Directed by: Tamra Davis
    In the comedic realm, Half Baked stands as an emblem of stoner humor. The story orbits around three hapless New York City friends - Thurgood (Dave Chappelle), Scarface (Guillermo Diaz), and Brian (Jim Breuer) who hatch a half-baked plan to free their fellow pot-lover, Kenny (Harland Williams), from prison. Their scheme? Sell marijuana stolen from a top-secret laboratory. Navigating a maze of madcap adventures and hilarious mishaps, this quartet of misfits stumbles through NYC's underbelly, engaging with an array of eccentric characters. A comedy of highs and lows, Half Baked is a cult classic that paints a vibrant picture of friendship in the face of adversity.

    Available On:

    subscription

    free

  • Con Air
    2

    Con Air

    Nicolas Cage, John Cusack, John Malkovich
    24 votes
    • Released: 1997
    • Directed by: Simon West
    In Con Air, Cameron Poe (Nicolas Cage), a newly released ex-con and former U.S. Ranger, finds himself trapped on a prisoner transport plane when the passengers seize control. Among them is Cyrus 'The Virus' Grissom (John Malkovich), a cunning and ruthless criminal mastermind. With help from U.S. Marshal Vince Larkin (John Cusack), Poe must thwart their deadly plans, save his friend Baby-O (Mykelti Williamson) and get home to his daughter. This action-packed thriller, directed by Simon West, blends high-stakes tension with explosive spectacle, delivering a wild ride in the sky.

    Available On:

    subscription

  • Undercover Brother
    3

    Undercover Brother

    Eddie Griffin, Chris Kattan, Denise Richards
    41 votes
    • Released: 2002
    • Directed by: Malcolm D. Lee
    Blasted from the past and ready to take care of business, "Undercover Brother" is recruited to infiltrate a sinister underground movement headed by The Man. Partnered with the sassy, stunning Sistah Girl (Aunjanue Ellis), our hero must first undergo the ultimate attitude adjustment and trade in his 'fro and platforms for tennis sweaters and penny loafers. Once the transformation is complete, he's ready to take on the evil perpetrators of Operation Whitewash.

    Available On:

    subscription

  • Blue Streak
    4

    Blue Streak

    Martin Lawrence, Luke Wilson, Peter Greene
    30 votes
    • Released: 1999
    • Directed by: Les Mayfield
    When a heist goes wrong, thief Miles (Martin Lawrence) hides a diamond at a construction site before he's arrested. After serving two years, Miles returns to the location of his treasure and finds it is now a police station. Disguising himself as a recently transferred officer to infiltrate the building, Miles stops an escaping thief while trying to retrieve the jewel. Impressed by his quick action, superior Rizzo (Graham Beckel) partners him with the bumbling detective Casey (Luke Wilson).

    Available On:

    subscription

  • Robin Hood: Men in Tights
    5

    Robin Hood: Men in Tights

    Cary Elwes, Richard Lewis, Roger Rees
    29 votes
    • Released: 1993
    • Directed by: Mel Brooks
    Unleashing a volley of humor in the classic vein of slapstick, Robin Hood: Men in Tights is a parody that reimagines the legendary tale of the bow-wielding hero. Robin of Loxley (Cary Elwes) returns to England after fighting in the Crusades, only to find his home ravaged by the dastardly Sheriff of Rottingham (Roger Rees). Aided by his band of merry men - including Blinkin (Mark Blankfield), Ahchoo (Dave Chappelle), and Little John (Eric Allan Kramer) - Robin sets out to reclaim his land and win the heart of Maid Marian (Amy Yasbeck). This comic romp, directed by Mel Brooks, skewers everything from the original folklore to modern pop culture, adding a unique layer to this timeless story.

    Available On:

    subscription

  • Dave Chappelle: Killin' Them Softly
    6

    Dave Chappelle: Killin' Them Softly

    Dave Chappelle, Albert Precourt
    29 votes
    • Released: 2000
    • Directed by: Stan Lathan
    Dave Chappelle: Killin' Them Softly is a 2000 comedy documentary film written by Dave Chappelle and directed by Stan Lathan.