It started with one post where Oswalt explained he performed a recent show with Chappelle, Oswalt took to social media with a note saying that Chappelle had texted him to come visit and do a guest set at the arena he was performing in next door.
“Why not? I waved good-bye to this hell-year with a genius that I started comedy with 34 years ago. He works an arena like he’s talking to one person and charming their skin off. Anyway, I ended the year with a real friend and a deep laugh. can’t ask for much more,” Oswalt wrote.
After some backlash, Oswalt wrote a follow-up post, saying he’s been friends with Chappelle since they were teenagers and hadn’t seen each other in a long time.
“He’s a fellow comedian, the funniest I’ve ever met. I wanted to post a pic & an IG story about it — so I did. The friend is Dave Chappelle. Thirty four YEARS we’ve been friends,” he wrote. “We’ve done bad & good gigs, open mikes & TV tapings.”
Oswalt also addressed Chappelle’s latest standup special, “The Closer,” and the fallout after its release in which some Netflix employees had walked out over the streamer’s decision to run the special. Oswalt wrote, “we 100% disagree about transgender rights & representation. I support trans peoples’ rights — ANYONE’S rights — to live safely in the world as their fullest selves.”
He added that he will “always disagree” with Chappelle’s stance on LGBTQ+ lives, he doesn’t “believe a seeker like him is done evolving, learning.”
“You know someone that long, see the struggles and changes, it’s impossible to cut them off. Impossible not to be hopeful and open and cheer them on,” Oswalt wrote. “I’m an LGBTQ ally. I’m a loyal friend. There’s friction in those traits that I need to reconcile myself, and not let cause feels of betrayal in ANYONE else.”
He added that he’d been “carrying a lot of guilt” after cutting off friends who behaved in ways he couldn’t live with.