He’s a legend in his own right.

Chappelle has certainly come a long way from a young standup to a mega star.

It wasn’t always easy in New York.

Dave Chappelle

While in the Big Apple, Chappelle performed a comedy set during amateur night at the renowned Apollo Theater.

However, his set didn’t go as planned as the crowd booed him off the stage.

While he found few favors through the deal, things ultimately didn’t turn out as he had planned.

Dave Chappelle poses at event

That one hopeful series, ABC’s “Buddies,” was unfortunately canceled after only 13 episodes.

“I flew out there for the meeting,” Chappelle told CBS News.

For no other reason than they thought it would give the show a more universal appeal.

Dave Chappelle looking on

And so I quit."

Chappelle returned with another television special with 2004’s “Dave Chappelle: For What It’s Worth.”

“And the sum of the conversation was, ‘I’m completely at peace with this.

Dave Chappelle smiles

It’s edgy, it’s scary, it’s wild.'”

According toCelebrity Net Worth, Chappelle unexpectedly walked away from the show during the making of its third season.

After his infamous departure, the comedian made headlines when he took a trip to South Africa.

Chappelle at The Kennedy Center

“I felt like some kind of prostitute or something.

If I feel so bad, why keep on showing up to this place?

I’m going to Africa.”

Dave Chappelle

According toCelebrity Net Worth, Chappelle performed sporadically in various venues from 2005 to 2013.

Chappelle made his full comeback to the comedy scene in 2013.

In 2014, the comedian headlined 10 nights at Radio City Music Hall in New York City.

Portrait of Dave Chappelle

The contract was said to be one of the highest-paying deals for a comedian of all time.

Chappelle’s comeback specials were not only anticipated, they were widely successful.

Netflix laterannounceda fourth Chappelle standup special in December 2017.

Dave Chappelle at Netflix event

Emmy Awards aren’t the only accolades Chappelle has.

The legendary comedian alsowon Best Comedy Albumat the Grammy Awards for three consecutive years.

In 2019, Chappelle received the Mark Twain Prize for American Humor at the Kennedy Center in his hometown.

Dave Chappelle on awards stage

“I love my art form,” Chappelle said during his acceptance speech,The Washington Postreported.

“It saved my life.”