Dave Chappelle is no stranger to controversy. Twelve years ago, at the height of his career, Chappelle walked away from his hit television show and a $50 million deal with Comedy Central. So many Chappelle’s Show segments—and not just the ones he did about Rick James, Charlie Murphy, and Prince—have already become the stuff of legend, and the show is rightfully credited for dramatically changing the way American audiences think, talk, and laugh about race.

For several years he stayed out of the public eye, but Chappelle has gradually raised his profile back to its previously lofty heights, most notably as host of Saturday Night Live the weekend after President Donald Trump’s election. Still, it was Tuesday’s release of two new comedy specials—filmed at Austin City Limits Live in April 2015 and at the Hollywood Palladium in March 2016, part of a three-special deal he signed with Netflix for a reported $60 million—that was supposed to mark the legendary comic’s triumphant return. To say anticipation has been running high is no small understatement.

I watched both specials back to back. I laughed, a lot. But I cringed more times than I should have. You can forgive a ballsy comedian like Chappelle a couple of lame LGBT jokes—pushing buttons is what he does, and goodness knows PC culture deserves some skewering every now and then. But Chappelle spends an awful lot of time in these specials discussing LGBT issues. They are easily the least funny parts, mostly because they showcase a man who seems stuck in a time warp, hung up about things he really shouldn’t be hung up about.

This is hardly the first time Chappelle’s material has been called homophobic. Just this past November, a gig he did at The Cutting Room in New York City left many progressives cold (while winning over many on the right). Why does Chapelle feel so compelled to return again and again to these topics, especially if he’s not going to offer a fresh perspective on them?

Chappelle’s go-to voice for every gay man in his two specials—high-pitched, over-enunciated, effete—is one that most people will recognize from comedians and television shows from the 1980s and 90s. His riff on how gays “always have some kind of political argument” comes with a curious example about how he had argued with a gay man who was petitioning to remove the words “husband” and “wife” from marriage licenses. “Nigga please, save me the semantics,” Chappelle says. “Take your chips out of the casino, you’re about to crap out. Go outside, talk it over amongst yourselves, and whichever one of you is gayer, that’s the wife.”