Dave Chappelle has always had a connection with hip-hop that resurfaces in the media every few years. From his history of hilarious rapper-driven sketches to his recent appearance on Saturday Night Live alongside A Tribe Called Quest, the comedian has relations in the hip-hop world of the upper echelon that many don't come by often. Kanye West once even performed for Dave at Radio City Music Hall for free—Not many can get that out of 'Ye.

Over the past decade, Dave Chappelle has maintained an array of top tier rapper relations in efforts to fuse the worlds of comedy and hip-hop to his liking. In 2006, Dave actually released a film, Dave Chappelle's Block Party, in which the comedian invited a slew of rappers to perform in the movie including The Fugees, Kanye West and Mos Def. The film was an instant hit in the rap world garnering tens of millions at the box office—not to mention the soundtrack to the film was dedicated to J Dilla.

While Dave Chappelle's connection with hip-hop is fresh in everyone's mind following his appearance on Saturday Night Live alongside A Tribe Called Quest over the weekend, XXL got to thinking about all the hip-hop moments with Dave witnessed over the years. While many moments come to mind, XXL picked out some of the most memorable in the list below.

  • 1

    When Dave Chappelle Hosted SNL With Musical Guests A Tribe Called Quest

  • 2

    When Dave Chappelle Hosted G-Unit's Bulletproof Mixtape

  • 3

    When Dave Chappelle Was Featured on The Roots' "In Love With the Mic"

  • 4

    When Dave Chappelle Was Featured on Talib Kweli & Hi-Tek's Reflection Eternal Album

  • 5

    When Dave Chappelle Joked About Ja Rule's Feelings on 9/11

  • 6

    When Dave Chappelle Did the "Rick James (Interlude)" on 213's The Hard Way Album

  • 7

    When Dave Chappelle Played Rapper Sir Smoke-A-Lot in Half Baked

  • 8

    When Dave Chappelle Said He Knew Kanye West Would Be a Star

  • 9

    When Dave Chappelle's Threw a Hip-Hop Block Party

  • 10

    When Dave Chapelle Reenacted Eminem's 8 Mile

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