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In only three short seasons, Dave Chappelle and his half hour comedy show Chappelle’s Show set the standard for all other variety shows to come. The comedian gave us some of the most memorable skits and characters in TV history, introduced the world to groundbreaking musicians, provided unprecedented social commentary on what it meant to be black in America, and showed us a very different side of Wayne Brady.

The series, which aired for two full seasons and one shortened third season, featured a number of then-underground Hip Hop and R ‘n B acts that had previously experienced little or no television presence. Performing on Chappelle’s Show helped build the careers by providing a wider mainstream audience for artists like Common, Talib Kweli, Mos Def, The Roots, Erykah Badu, Cee Lo Green, and Ludacris.

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While Chappelle broke ground as one of the first black comedians on a mainstream channel to tackle race and identity, the comedian cited viewers’ misconceptions as one of the reasons he famously walked away from his $55 million pay cheque.

With Chappelle set to host Saturday Night Live this week, we can’t think of a better time to revisit Chappelle’s Show, which originally aired from 2003 to 2006. In three seasons, Chapelle changed pop culture in a show that was so funny it sent Charlie Sheen to the hospital. Seriously.

Playa Haters Ball

Before we sent haters to the left, haters to the back, and were told to shake off the haters, Dave Chappelle was throwing the Annual Playa Haters Ball. The skit paved the way for the word ‘haters’ to become an integral part of North American slang and gave Ice Cube a break from playing a detective on Law and Order: SVU.

The Dark Side Of Wayne Brady

In 2004, comedian Wayne Brady was best known for his lighting speed wit on the family-friendly improv comedy series Whose Line Is It Anyway, and as the host of the variety series The Wayne Brady Show. The world saw a whole new, hilarious side of the G-rated Brady when he appeared as himself on Chappelle’s Show, albeit a version of himself who was a violent pimp. So, really just the name was the same. The sketch, written by Brady, Chappelle, and comedy writer Neal Brennan, earned a spot in the Television Museum of History and has gone on to largely define Brady’s impressive career.

Kanye West’s First TV Performance

In Season 2 of Chappelle’s Show, musical guest Kanye West had only just released his first album The College Dropout a month before, with the rapper still a virtual unknown. Taking the advice of his friend, musician Common, Chappelle booked the then-unknown West as the musical guest for his show, marking West’s first-ever TV performance. His life was dope and he did dope shit.

John Mayer’s New Gig

In 2004, John Mayer seemed like just another bland, indistinguishable Dave Matthews clone. Years before his sexual napalm comments and high profile relationships, Chappelle booked the singer/songwriter on his show and included him in a skit that put Mayer in a whole new light – guy with a sense of humour.

A Moment In The Life of Lil Jon

Thanks to his trademark ‘YEAH’ and ‘WHAT,’ rapper Lil Jon became a favourite character for Chappelle, who used only those two phrases when playing the rapper in his ongoing ‘A Moment In The Life Of Lil Jon’ skits. And yes, that’s Susan Sarandon.

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Rick James, Bitch

In the first installment of True Hollywood Stories on Chappelle’s Show, Chappelle invited actor Eddie Murphy’s older brother Charlie to recall some of the duo’s wilder moments in Hollywood. The first legendary skit was courtesy of Murphy’s story about his time fighting Rick James, with a hilarious impression of James by Chappelle. What made the skit even more iconic was the addition of an interview with the actual Rick James, who confirmed Murphy’s story. The skit gave the world the legendary line “I’m Rick James, bitch!”

Shooting Hoops With Prince

Chappelle again enlisted Charlie Murphy to re-create the time that Murphy played basketball with Prince. The famous skit even found a fan in Prince, who used an image of Chappelle in his Prince outfit on the cover of his album. The skit resulted in a friendship between Prince and Chappelle and following Prince’s death earlier this year, the skit was viewed over 600,000 times on YouTube. Legendary.

Starting November 25, you can stream all three seasons of Chapelle’s Show on CraveTV.