Dave Chapelle was a household name during the early 2000s due to Comedy Central’s hit show, Chappelle’s Show. Dave gained a cult-like following thanks to the comedian’s hilarious commentary on social issues, viral catchphrases, and witty skits. However, three years in, Dave rejected a $50 million deal to produce two more seasons, a decision he is said to have regretted a couple of years later. Dave cited that the way he used to push TV boundaries didn’t feel right and the emotional connection with the content he was creating was not there.