Chappelle's fans have been waiting for his return to television ever since.
The comic is now back with not one, but two stand up specials releasing on Netflix Tuesday -- part of a three-show deal Chappelle inked with the streaming giant last fall.
In honor of his return, here are a few facts about the comedian you may not know:
While much is being made of Chappelle being back in the spotlight, he never really left.
He popped up at various comedy venues from time to time and told People
in 2014, "I never stopped being on stage."
"What I did was step off of the main stage," he said. "Because those lights were hot, and I was trying to do other things with my life."
Chappelle stays far from Hollywood
Some folks were surprised when the performer recently showed up at a village council meeting in Yellow Springs, Ohio.
But Chappelle lives in the area and spoke out as a citizen to offer his thoughts on local policing.
"In this Trump era, there's an opportunity to show everybody that local politics reigns supreme," he said. "We can make our corner of the world outstanding."
Chappelle lives on a 65-acre farm with his wife, Elaine and their three children.
Residing in Ohio, according to Chappelle, is a nice balance to being a celeb.
"I still travel all the time, but it's still nice to have 65 acres to just chill out," the "Half Baked" star told MTV
Yes, he walked away from $50 million, however
Chappelle attributed his decision to leave his wildly popular "Chappelle's Show" to fatigue, a loss of creative control and discomfort with the material.
"I was doing sketches that were funny, but socially irresponsible," he told Oprah Winfrey during a 2006 interview. "I feel like I was deliberately being encouraged and I was overwhelmed."
Chappelle doesn't hate "Key & Peele"
Over the years, Chappelle has made some discouraging comments about the duo, whose Comedy Central show was viewed -- by some -- as the heir to Chappelle's.
The star told "CBS This Morning" that he liked "Key & Peele," but felt their comedic format and brand of humor mimicked his.
"At the end of the show, it says created by Key and Peele," Chappelle said. "That hurts my feelings."