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Whitmer Thomas serves standup with a beat

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During one of his witty pop songs, Whitmer Thomas drops the line “Cynicism isn’t nice, but it’s (bleeping) funny!” These are words that the 33-year-old songwriter and comedian tries to live by.

“I can’t allow myself to process things without turning it into a joke,” he said by phone this week. “That’s something I grapple with a little bit in the show I’m doing– I want to be more ticked off, more of a bitter and angry person. But thanks to the way I was raised, I don’t really have the skills to do that.”

Thomas was an indie rocker before he did standup, but for him the two things have always flowed together. His show at O’Brien’s in Allston Nov. 8 will be unusual in that he’s playing a rock venue instead of a theater. But the show will still be largely spoken-word, with songs inserted at the right dramatic moments. He’ll be dealing with painful childhood memories, family alcoholism, lingering self-doubt, and other things that you wouldn’t usually expect to laugh at.

“I feel that grief is a pretty untapped vein in comedy. And really, there’s nothing better than talking to a group of people who have dead parents, or who’ve also lost friends– It’s a cathartic experience to be around comedians because they’ll make fun of that person in a loving kind of way. The truth is that I’m always trying to be as funny as I can, but there are times in the show where I say ‘Damn it, I have to be serious now’. I hope the stories are silly enough that I don’t have to force laughter in the serious parts.”

As a songwriter, he brings to mind sensitive and self-deprecating types like Paul Westerberg and Elliott Smith, and he says he’s a fan of both. “I tried doing just music but could never get anywhere with it. I was in a band that was way too goofy for LA — We came from small towns [Thomas is from Gulf Shores, Alabama], and we talked too much onstage — so we just dropped the instruments and wound up doing sketch comedy. Then I recorded a very serious, hyper-sincere record and I was so embarrassed by it that I started changing the words, if there was a line that was almost poetic I’d make fun of it.” One of his most intense songs, about his mother’s alcoholism, wound up spawning a comic routine. “I just started singing “My Mommy partied to death,’ and it was so aggressive that people laughed at it. I think it’s healthy to be stupid and silly about his kind of stuff, but my therapist probably doesn’t.”

He dealt with family history in his first one-man show, “The Golden One,” which became an HBO special. The current sequel, “The Older I Get the Funnier I Was,” picks up from his adolescence. “My dream would be to be a comic who people think is relatable, and whose jokes get shared on TikTok. But I don’t know if I’ll ever break into the mainstream, because it’s always going to be very specific people who find me funny. Every time I try to do a broader observational joke, I find it really hard because people have done so many.”

And now that he’s done childhood and adolescence, what’s next? “I’ll probably have to start my own family. Either that or retire.”

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