I have a weird relationship with Dave Chappelle ... I never found him very funny. I think us senior GenXers are just outside of the Chappelle window... we had SNL and SCTV, while the younger of my generation had Kids In The Hall, Almost Live, In Living Color, Up All Night, etc., and I never really liked that era of comedy. Which is where people like Chappelle and Chris Rock and the Wayans brothers came up.

So I missed that boat.

But Dave Letterman's new show, "My Next Guest Needs No Introduction" is a long-form interview format where Dave just sits and talks with someone he likes/respects very much.

His interview with Dave Chappelle was fascinating and made me love Chappelle, and what he has done with his life. The little town he lives in. The way he lives with his family and friends, and the community he has created around him as he has matured and mellowed over time.

... then this trans-phobic dude comes out of Chappelle's skin, and starts saying really stupid, ill-informed shit about an entire class of people who are finally getting some liberty and recognition, and not being ground under the boot of white American culture-leaders... and Chappelle takes the ENTIRELY wrong position.

And doubles-down on it. Again and again.

I have a hard time squaring the quiet, respectful, community-building family-man I saw Dave Letterman interview, with the on-stage dipshittery of Dave Chappelle's "comedy" show?!?

I'm not losing anything by tuning out Dave Chappelle, and I will happily continue to do so. But I wonder where the split is in his brain, where he fails to apply his worldview and generosity equally, and especially in the case of an abused minority, like trans people.

It's weird that he doesn't see it.