A Complete History Of Dave Chappelle’s Terrible Chappelle’s Show Monologue Outfits

Show me someone who genuinely doesn't like Chappelle's Show, and I'll show you someone who has either never seen it or is a certifiable lunatic. When the show debuted on January 22, 2003 (yes, over 10 years ago), it instantly established itself as something special. Chappelle's trademark racial commentary and off-color humor was not hindered by the sketch format, but rather given a platform to come to life via hysterical original characters (Tryone Biggums) and A+ celebrity parodies (Lil Jon), all the while illuminating America's ever-present social issues. Part of the show's legacy stems from its controversial and highly-publicized ending, but in its short 25 episode run it earned a definitive spot on Television's comedy Mount Rushmore. Meanwhile, 9 years later, Comedy Central continues to struggle to find a sketch show even remotely as funny or intelligent (Kroll Show? Key & Peele? Nope).

And yet, like seemingly every comedian ever (minus maybe Aziz Ansari), when it came to style, Dave Chappelle's opening monologue fits were less than stellar. From giant pants to jackets that I honestly would otherwise have no idea existed, his looks were heavily influenced by oversized, men-should-not-care-about-clothes attitudes of the time. In essence, Dave looked straight out of a JCPenney catalog, and not the current, Nick Wooster-inspired kind. What this means for style as a concept is that in rare instances, a person's brilliance can overcome their horrible taste in clothing. Once in a while, a person is so good at something that it's accounts for all the swag they would ever need. Dave Chappelle is without a doubt one of the greatest comedians of all time, thus, we will remember him for his jokes, not his jeans—his once-in-a-generation decision to give up superstardom, not his regrettable collection of newsboy caps. So, in very un-Four Pins like manner, we aren't going to waste our time making jokes about Chappelle's outfits. Instead, for your viewing pleasure, we've simply cataloged each of his opening monologue outfits using kind-of-shitty-res images because Netflix is fucking up and no longer streams arguably the funniest show of the past 10 years.

  • booboobb

    this is great, i used to know if i watched an episode or not based of his outfits

  • Ghost

    An article based on his clothing being not that cool when this show is a decade old? Weak.

  • WAVY

    Rocking the Supreme Basquiat collection on slide 12 lol

  • Noah

    If you go from season 1 to season 2 you’ll notice a huge change in his looks. Everybody even remotely involved with hip-hop community was rocking baggy shit back then, but by season 2 he started wearing Supreme, Rogan, Stone Island, and Nice Collective amongst others. He also switched from those wack Diesel sneakers to retro Nikes. His stylist new she had to step it up.

  • ryan

    $50 Million buys a lot of denim

  • squatty

    here’s a better question: how did jake wolff dress ten years ago? fuck that fag.

  • squatty

    jake woolf: internet’s joan rivers

    • OK_ok

      ok you actually won

  • Sumidiho

    He was in style for that era …that’s over TEN years old

  • akabaloo

    And then Wayne Brady happened

  • tatsu

    it was considered stylish for the time, i’m pretty sure everyone went through this phase or something similar to it. And key & peele is hilarious.

  • KrayKray

    i always liked the way he dresses….

  • Class A Rando

    WAIT TILL YOU SEEM HIT WAIT TILL YOU SEEM HIT WAAIT TILL YOU SEEEEMM HIIIITTT