Timothy Olyphant Was A Failed Stand Up Comedian Before He Was A Star

Those who only know Timothy Olyphant from television series like Deadwood and Justified, or movies like Hitman or even the upcoming Quentin Tarantino joint, Once Upon a Time in Hollywood, may not realize how screamingly funny the actor can be. There’s plenty of evidence of it, however, from his guest stint on The League, three seasons of Santa Clarita Diet (RIP), or his many appearances on Conan O’Brien or Seth Meyers. In addition to being a dashing, charming, and talented actor, Olyphant is also very funny.

That makes more sense when one realizes that, before his big break in movies like Scream 2 and Go back in the late 1990s, Olyphant dabbled in the world of stand up for a year or two. In fact, though Marc Maron doesn’t remember him, Olyphant and he were in the “same gang” of comedians at the Boston Comedy Club in the early ’90s, which is also where Sarah Silverman got her start as a barker. In fact, years later, Sarah Silverman approached Olyphant at a party to say how much he loved his work, and he said, “Sarah, don’t you remember me” (She did not).

Talking with Maron on the WTF Podcast this week, Olyphant recalled that he was doing open mics there at the same time as other notable comedians were getting started at the Boston Comedy Club, like future SNL cast member Jay Mohr (with whom Olyphant co-starred in Go), Dave Atell, and Louis C.K.

Olyphant, in fact, got his start at The Boston the way so many other stand-up comedians had before: By handing out flyers to passersby in exchange for time on stage (the practice, in fact, is documented in Pete Holmes’ HBO series Crashing). Stand-up initially came easy to the actor. “I’d always heard that you’re just going to bomb for a while,” he told Maron on the WTF podcast. “I felt like I had a couple of shows right out of the gate where I was like, ‘This is easy. This is great.’ And then the bombing started.”

Olyphant, who was a fine arts major in college, took inspiration from Steve Martin on stage, doing oddball stuff where he’d come out “and start singing ‘If You’re Happy and You Know It (Clap Your Hands),’ and I would continue to sing it with enthusiasm no matter what the response was. I thought it was conceptually awesome.” Olyphant also said that he felt like he had one smart joke. It was about art and pornography, and about the difference between the two. Basically, he took a serious-minded, well-spoken quote from a famous artist about the purpose of pornography — to titillate, etc., — and just added at the end of the quote, “And it matches your furniture.”

“That was the closest thing I came to a ‘smart’ joke,” Olyphant said, “and then I just did an M.C. Hammer joke about the song “Can’t Touch This,” and how Olyphant “didn’t want to touch it. I don’t want to touch it.”

Ultimately, Olyphant abandoned his stand-up comedy ambitions for a couple of reasons. He couldn’t handle the “awful” schedule of a stand-up comic, and also because “hanging out with [other] comics was not so fun.” Olyphant was also concerned that he might eventually be good enough as a stand-up that he’d land a sitcom making a lot of money and “end up one note … and this will all be over before I’m 30.”

Olyphant almost certainly made the right decision in his career, given the longevity of it, although he is still very funny. To wit: He and his wife have been together since college, they have three kids, and his oldest daughter is attending college at the same school where Felicity Huffman and Lori Loughin’s children attend. “It’s funny,” Olyphant told Maron. “I gotta kid in college on a tennis scholarship, and it never occurred to me she never even had to play. It’s f**cked up. We even got her the lessons and everything. We just weren’t thinking creatively enough.”

He’s still got it.

Olyphant can currently be found in HBO’s fantastic Deadwood movie.