While attending high school at the Duke Ellington School of Arts, Chappelle started performing stand-up comedy. He was not old enough to enter most clubs by himself, so his mother had to go with him. As a teenager, he was always pushing people’s buttons and was even booed offstage during amateur night at the Apollo Theatre. He skipped college to focus on comedy full time, and in 1994 he became the youngest comedian to be featured on the HBO special Comic Relief VI. At the young age of 18, Chappelle was getting offers from TV networks to star in comedy pilots. None of the pilots were really successful, but that didn’t stop his blossoming career. He had appearances in multiple movies in the mid-to-late ‘90s, and then released his popular HBO comedy special, Killin’ Them Softly in 2000. The one-hour stand-up special was a massive hit and made him even more of a superstar in the comedy world. Dave Chappelle’s net worth was growing. And then in 2003, he landed his own sketch comedy show on Comedy Central called Chappelle’s Show. The show was insanely popular and Chappelle was reportedly offered a $50 million contract for two additional years. Dave Chappelle has become a household name like Beyonce and Jay Z. But just as the show was about to start filming its third season, Chappelle left and took a random trip to South Africa. He was unhappy with the show’s direction and had too much stress and pressure coming down from the execs at Comedy Central. He left the show and gave up his $50 million contract. Dave Chappelle’s net worth declined over the next two years, but it was not a significant drop. Once he returned from South Africa, he started living a quiet life in Ohio, only making a handful of appearances for several years until he made his comeback in 2013. He slowly started getting back on the comedy stage. It was rough at first. He even got booed a few times, but eventually he found his groove again. He made appearances on multiple late night shows in 2014 and in 2016, he made his hosting debut on Saturday Night Live. In November of 2016, Netflix announced that Chappelle would be releasing three comedy specials on their streaming service in 2017. He reportedly got $20 million for each special, which means he earned an insane $60 million. In January 2018, his comeback was complete as he won the award for Best Comedy Album at the 60th Grammy Awards for his first two specials on Netflix. According to the most recent reports, Chappelle’s net worth is around $42 million, thanks in large part to his record-breaking deal with Netflix.
