I don't know but he was doing tv & film before Chappelle SHow and it was with A List talent. You can't convince me Dave wasn't a millionaire before 03.
At 19, he made his film debut as "Ahchoo" in Mel Brooks' Robin Hood: Men in Tights. He also appeared on
Star Search three times but lost to competing comedian
Lester Barrie; Chappelle later joked about becoming more successful than Barrie.
The same year, Chappelle was offered the role of Benjamin Buford "Bubba" Blue in Forrest Gump. Concerned the character was demeaning and the movie would bomb, he turned down the part.[20][21] He parodied the film in the 1997 short
Bowl of Pork, where a dim-witted black man is responsible for the
Rodney King beating, the
LA riots and
O. J. Simpson's being accused of murder.
[22] Chappelle played another supporting role in an early
Doug Liman film,
Getting In, in 1994.
[23] At age 19, he was the opening act for R&B soul singer
Aretha Franklin.
[24]
Chappelle attracted the attention of television network executives and developed numerous
pilots but none were picked up for development into a series.
[12][25] In 1995, he made a guest appearance on an episode of ABC's popular
sitcom Home Improvement.
He later appeared as a stand-up insult comic who targets patrons of a nightclub in the 1
996 comedy The Nutty Professor starring Eddie Murphy, one of his major comedic influences.
[28] He had a minor role in
1997's Con Air.[29] At the beginning of 1998, he did a stand-up performance for
HBO Comedy Half-Hour. That same year, he appeared in "Pilots and Pens Lost", an episode of
The Larry Sanders Show's sixth season, in which he and the executives of the show's unnamed
television network satirize the treatment that scriptwriters and show creators were subjected to, as well as the executives' knee-jerk tendencies toward
racial stereotypes.
[30]
He and
Neal Brennan co-wrote the 1998
cult stoner film Half Baked, Chappelle's first starring role, about a group of
marijuana-smoking friends trying to get their other friend out of jail. It made money at the box office and remains a classic "stoner" film, a genre that includes the
Cheech & Chong films as well as more recent fare like
Judd Apatow's
Pineapple Express.
[31][32] In December 1998, Chappelle appeared as
Tom Hanks' character's friend and confidant in
You've Got Mail.
[33] In 1999, he appeared in the
Martin Lawrence film
Blue Streak.[34]
In 2000, Chappelle recorded his first hour-long HBO special, Dave Chappelle: Killin' Them Softly, in
Washington, D.C. He also starred alongside
Norm Macdonald in the 2000 comedy film
Screwed.
[35] He followed this with an appearance as "Conspiracy Brother" in the 2002 racial satire
Undercover Brother.
[36] During the early 2000s, Chappelle was a member of the
Spitkicker artist collective, along with many
hip-hop artists like
De La Soul and
Talib Kweli.
[37]