A trans woman, a lesbian, an Indian American man, and a black man walk into a bar in Portland, and turn about 100 white people various shades of uncomfortable.

At least, that’s what emanated from the Analog Theater last night during W. Kamau Bell and Friends, a showcase for the host of the lamentably canceled TV show Totally Biased and a few of his funny friends. You could feel the air shift in the room at various times throughout the evening when discussions of class, gender, and racial issues forced these so-called progressive comedy fans to ask some difficult questions of themselves.

The best example was when trans comic Natasha Muse announced that she and her wife had a baby recently. Usually, that’s a line that would warrant a bit of applause from the audience. Instead, it was greeted with near silence. Were folks still trying to come to terms with the idea that she married a woman? Or wondering how the wife got impregnated? Muse took it in stride and instead turned to her realizing that, in spite of her early insistence that she wouldn’t talk to her baby in a sing-song voice, she soon found out the alternative is much creepier. Try reading these lines in a flat monotone you’ll see what she means: “Who’s a good girl? Are you a good girl? Who’s a dirty girl?”

And so it went through most of the evening. The crowd would veer from awkward silences to gales of laughter. Bell and one of his former cohorts on Totally Biased, Hari Kondabolu, had to deal with the biggest shifts in mood. Folks seemed a little weirded out by Bell’s impression of gun nuts jerking off all over their arsenal of weapons but loved his impression of a conservative forced to applaud the gay Latino who came to Gabrielle Giffords aid right after she was shot in 2011. Too, Kondabolu’s jabs at Portland were welcome, but no one was willing to jibe with his brilliant feminist dick joke (I won’t spell it out for you here; find it on his recently released album Waiting for 2042).

I’m hoping that what came out of last night’s show was what Bell has long wanted from his standup and his TV work: to get people to have those awkward conversations about race, gender, class inequality, etc. Maybe those odd silences and bits of scattered laughter that came along at the more cutting jokes are were the seeds of those discussions being planted. One can only hope. But, hey, at least everyone in the room agreed on one thing Bell pointed out: putting Baron Vaughn’s New Negroes showcase on the MailChimp Stage was maybe not the best decision by Bridgetown organizers.