Patton Oswalt is a comedian I genuinely respect, one who seems to work insanely hard based on the number of things he shows up in on top of his stand-up tours. He’s in a lot of things I love, such as A.P. Bio and the MST3K reboot, so these days, he’s probably up there in “favorite comedian” status.

I was supposed to see him on tour at in March of 2020, but because of some stuff in the news you might have heard about, that was delayed until last fall. (I actually got a personal apology for the rescheduling on Twitter, which I guess is cool.) But despite the rescheduling, I still made it a year and a half later.

On top of that, he has generally stood up for others with his work and public profile. His comedy has generally avoided punching down for the sake of a good joke, and one gets the feeling that he’s not BSing you when he emphasizes his efforts to grow as a person. 

Over the weekend he had a bit of an incident where some of those things came into question, in part because of an old friendship with a comedian who had a very eventful (and controversial) 2021.

See, Oswalt grew up with Dave Chappelle, a comic with whom he shares a deep history, as both started their careers in the D.C. area and did many early performances together. While Chappelle is the bigger star, both have managed to become some of the most popular comedians of their generation.

However, Chappelle’s controversial anti-transgender jokes have not sat well with a lot of people, have drawn scores of protest, and ultimately could leave a permanent stain on his legacy. (They arguably already have for Netflix.) It’s a strange time for a fellow comedian to be highlighting his relationship with Chappelle, but that’s what Oswalt did over the weekend, by doing a surprise set at a New Year’s Eve event for the comic. Both were in the same city performing shows.

“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,” he wrote.

But the association between Oswalt and Chappelle highlights something complicated that I think a lot of folks with public profiles have had to learn how to navigate in recent years: when someone you know does something controversial, do you stand by them?

In a follow-up Instagram post, Oswalt emphasized that just because he showed up on Chappelle’s stage doesn’t mean he supports everything about him.

But he also made it clear he was struggling with this call, emphasizing Chappelle was a “seeker” who could still evolve on the issue. He also had broader issues at play beyond Chappelle:

I don’t think Oswalt made the right move by choosing to publicly emphasize that friendship with that person, at that time, in that way. But I understand why he wanted to, and can appreciate the thought process. Being on the other side of a personal relationship with someone who is facing controversy is not fun, and it tests your loyalties in important ways. I’ve seen this myself in the journalism space, and it led to some tough decisions about how close I stayed with some people. So I understand it.

Sometimes the call is harder than it looks, even if it means shouldering the weight of that controversy yourself.

Time limit given ⏲: 30 minutes

Time left on clock ⏲: 35 seconds

If you like this, be sure to check out more of my writing at Tedium: The Dull Side of the Internet.

Dig this issue? Let me know! (And make sure you tell others about MidRange!)