Brooks Wheelan sits at The Porthole located off Commercial Street in Portland, Maine, eating a lobster roll. This mucky waterfront eatery has been a Custom House Wharf mainstay since the 20s, and features a dock for cruise ships rolling in from the bay. Today it’s Casablanca Cruises, exiting a team of eager, hungry tourists.

A few blocks away is another area staple: the First Friday Art Walk is Maine’s largest free monthly cultural event. Taking place on the first Friday of every month, thousands of people drift into the city’s arts district to buy work from local artisans, take in live performances and stroll along city streets. Between the artists and merchants, and meandering guests, the Old Port area – especially here, circa MECA’s campus – is clustered. It’s summer in Maine.

Wheelan is in town for the third annual Portland Maine Comedy Festival, headlined by Maria Bamford. His show is located on the second floor of Empire; the first floor is a Chinese kitchen. There’s folding chairs and a few tables facing the stage. A group of overflow attendees are standing near the bathroom, so you have to weave your way through to use the toilet.

Four days earlier, across the country, a thief broke into Wheelan’s car, stealing his notebook of jokes and forcing him to rig up a slightly modified set. “The saddest part was it was the first book I was on the last page of, and I was so proud. I never fill them up,” he says.

It’s not his first visit to Portland. He previously performed at One Longfellow Square in the middle of his 2015 Oceans Rule tour. One Longfellow Square and Empire are similar, in keeping with the city’s hipster influence and (occasionally) ramshackle appearance. Established venues like the Improvs of the world come with built in audiences… as well as money guarantees. But playing at a place like Empire is more in Wheelan’s wheelhouse: they’re more intimate, no drink minimums, a genuine DIY aura.

“I love non-traditional comedy clubs more than anything.”

Wheelan opens with five minutes of material on navigating his way through First Friday during the walk over, before settling into his act. It’s a very loose atmosphere, enabling the former Saturday Night Live cast member to improvise. He doesn’t have his book, but he’s emboldened by the challenge. “A crowd at a place like this is very forgiving, and likes [spontaneity]. It allows me to be comfortable and tell jokes I hadn’t even thought of.”

Growing up, Wheelan got into open mics after his brother began bartending at one of the only comedy clubs in Iowa. His early influences included Mitch Hedberg’s Mitch All Together and Dane Cook’s Harmful If Swallowed, albums he wore out in his Geo Prizm. “Back when Comedy Central played half hour specials so constantly. I would absorb them.”

Now, several years removed from his stint on SNL, Wheelan’s association with the show feels like a footnote as he continues to branch out. There’s got to be a love/hate dynamic at play for a young comic looking to not be merely defined as an extension of Live From New York. “It can really launch you, or it could just be a stop on whatever career path you have. And I feel like that’s what it was for me… It gave me this career, in all honesty. People see those three letters and they’ll come see a show.”

As recently witnessed by Luke Null’s departure from the show, the modern iteration of SNL has a nasty habit of (perhaps) overstuffing its cast, hiring talented performers then letting them languish. For Wheelan, he’s clearly pivoted and moved on.

The first season will soon wrap on the Emmy-nominated Big Hero 6: The Series. Wheelan voices Fred on the Disney cartoon. (Former SNL alum who’ve also lent their voices to the show include Rob Riggle and Jon Rudinsky.) He also continues his podcast, Entry Level, which is about “all those jobs we’ve had that sucked.” Each episode Wheelan interviews a guest to “find out what garbage they had to put up.” Previous guests include Kyle Mooney, Sean Patton and Nick Rutherford.

“I have been fired from so many jobs, and I have quit so many jobs. And I have never cared about any job – ever. And I think a lot of comedians are the same way. Because we only ever wanted to do comedy. So I was like, let’s talk about that. Comedians are great storytellers, getting fired is a fun story, so let’s hear that.”

The prospects of landing a TV show persist as well. Based in LA, Wheelan has resumed writing (and pitching). “I moved to Los Angeles to make my own Always Sunny in Philadelphia, and the bump on the road was moving to New York to do SNL, so now I’m back there working on TV shows again.”

There’s no question, however, Wheelan’s most at home on stage… which sounds cliché, like PR boilerplate but it’s true. He shifts gears seamlessly: poignant one moment, then incisive the next. There’s this undercurrent of rage that boils up at strange, clever times as well, like when he lacerates the cartoon musical Pocahontas for not featuring talking animals. (Note: John Candy initially recorded dialogue as a talking turkey before his death.) It’s so specific and weird.

For the crowd of likeminded millennials, it’s a pitch-perfect rant.

“It’s my job. It’s the only thing I truly care about in this world… the only thing I want to go down as is being a great standup comedian. That’s the only thing that really matters.”

Wheelan’s closer is particularly fun: he walks off stage, before returning for a post-game conference – sweaty and wearing sunglasses – taking questions from the audience. It’s a great way to engage the crowd and acknowledge what worked and what didn’t. He’s playing a character, but the bit never comes off like a stunt or gimmick. It just works.

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