The word “surreal” pops up frequently when Emma Willmann, who plays Laugh Boston next week, talks about her appearance on “The Late Show With Stephen Colbert” in September. The night the Maine native was originally slated to tape her standup spot, there was only one other guest on the show: Bruce Springsteen. The show sent a car to pick her up, and she was greeted with a throng of fans at the Ed Sullivan Theater, who were immediately disappointed when she stepped out of the car and was not The Boss. She thought they were booing her, but realized later, they were just yelling “Bruce!”
She taped her spot, but got bumped from the broadcast when Colbert and Springsteen talked for the whole show. This was going to be her network TV debut, but she wasn’t disappointed when she found out it wouldn’t air. “I was really, really, really relieved,” she says, “because it was a totally jarring start to the whole thing.”
Willmann was also relieved when they told her she’d be back on the following Monday, and she’d be doing her spot live. She wasn’t used to the fancy treatment of the CBS green room and all the perks. “Normally you’re at a comedy club and it’s very different from being at the Ed Sullivan Theater. It was just surreal.”
Nor was she ready for how time seemed suspended when she was doing her act on live TV. “Five minutes goes by very quickly.”
Willmann has been rising steadily in just a few short, strange years, but her career thus far has been a seemingly random series of ups and downs. In the past two years, she has been featured in the New Faces lineup at the Just for Laughs Festival in Montreal and landed a job hosting a standup show called “The Check Spot” on SiriusXM satellite radio. She’ll be headlining at Laugh Boston on Nov. 30 and Dec. 4, and appearing at Carly Aquilino’s shows Dec. 2-3.
The Blue Hill, Maine, native started performing comedy in Boston in 2010 after she saw another woman doing it at a party. Intrigued, Willmann went from trying standup at a friend’s queer poetry open mike to the Comedy Riots competition at Dick Doherty’s Beantown Comedy Vault, which was only her fourth or fifth time trying standup. “That was when I was like, oh my God, this is hard.”
She left Boston and went to grad school at New York City’s New School, and then came back to Boston and quit doing comedy for a year. “I promised myself and my parents that I would try to get interested in something else,” she says. She tried being an agent, but never landed a job, and when she moved back to New York and started standup again, she wound up signing with the agency that had rejected her as an agent.
Then came acting auditions. She was enthusiastic about adding to her resume, and wound up doing reenactments on the true crime show “Deadly Affairs” on the Investigation Discovery channel. “I got this thing playing a rugby coach, a murderer, and a detective, and this tiny line in a Sprint commercial,” she says. “That was all the first year I was going on auditions. Then I took a couple of acting classes. Now I’ve not gotten any roles. Do not take acting classes.”
That became problematic when she was working the college standup circuit, showing bookers her resume. “Then they’d pull up my reel and it’s just me being a murderer,” she says. “And they’d be, like, ‘Do you have anything else we can show our student activities board?’ ”
Still, she established herself at The Comedy Cellar in New York and got the SiriusXM and Just for Laughs gigs.
Explaining the break that got her on “Colbert,” Willmann says the show’s booker just happened to see her at the Cellar doing a set when she was “super loose,” despite a disastrous day coming back from a college gig in upstate New York. “I was really tired, I had just gotten this whopping speeding ticket. The car ride was supposed to be four hours but it was eight hours,” she says. “I know that doesn’t sound like the ingredients for a good set, but for whatever reason, it was.”
The booker immediately started working with Willmann on her set; it was a revelation to her. She had always talked about being gay in her act, but she was hesitant to go into too much detail about it. She wanted to be relatable. Then she did a routine about her mother finding her sex toys, and the Colbert booker encouraged her to explore topics like that more. “Now I’ve noticed the more open I am about like the weirdest stuff, the stuff I think no one could relate to, that’s actually oddly what people will react to more,” she says. “Someone might not be able to relate to the specific story, but everyone can relate to being embarrassed.”
More often lately, Willmann is discovering how much her identity as a gay woman is intertwined with her sense of humor. “Especially with the recent election, I’m not going to shy away from anything,” she says. “I used to always be, ‘Oh, I don’t want to be threatening, I don’t want to be too gay.’ I’m very friendly. If someone’s threatened by me, that’s crazy. Because I’m, like, an idiot.”
At Laugh Boston, Nov. 30 at 8 p.m. and Dec. 4 at 7 p.m. Tickets: $20,
Nick A. Zaino III can be reached at firstname.lastname@example.org.