Tim Ferrell sits at Blue, the live music and events venue, at 650 Congress Street. The venue also hosts live storytelling events and stand up shows, where students in Ferrell's comedy workshop classes perform. (Portland Phoenix/Evan Edmonds)
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Despite what some think, being funny is actually coachable. But Tim Ferrell doesn’t want you to know that.

The longtime Portland comic, comedy instructor and public speaking coach firmly believes that comedy doesn’t want to appear constructed or rehearsed — even when it is.

“What it wants to be is a live conversation,” Ferrell said. “Granted it’s one-sided, but that’s the trick, that’s the smoke and mirrors. Audiences want to believe you’re making it up on the spot as you go along. And if you’re good, that’s what it looks like.”

Ferrell, 67, spent his more than 20-year career immersed in the business of comedy, performance and presentation. He’s spent a lot of that time helping comics and public speakers seem naturally gifted. That is, uncoached.

Prior to coaching, Ferrell got his start in New York City, where he spent eight years in an off-Broadway production of “Naked Lunch,” an original play Ferrell wrote that re-stages the 1965 obscenity trial of Williams Burroughs’ novel. Somewhere in that time, he started teaching stand-up comedy — on a dare.

“No one was teaching or coaching standup. It seemed pretty pretentious. But I had the space and I started offering comedy workshops,” he said.

Two of his most recognizable students came from Ferrell’s time in New York, when he coached Jon Stewart, longtime host of The Daily Show on Comedy Central, and a then 15-year-old Chris Rock.

After years in the big city and on the road, Ferrell chose Portland as his long-term destination. That led to the Comedy Connection, but when it closed in 2012, Portland held even more opportunities for him to dive into.

There’s a “zillion” different ways to approach comedy, Ferrell said, whether it’s delivery style, content, physical behavior on stage or something else. Whether it’s stand-up or any form of public performance, Ferrell’s advise is to stay concise, start strong, and close strong. 

“If you think for a second that it’s not a coachable thing,” he says, grinning — “that’s what I want you to think!”

Ferrell’s career went all over before he touched down in Maine, but it was here in Portland where it was a “dream come true,” running the Portland Comedy Connection. In its heyday, the 156-seat venue on Custom House Wharfhosted multiple shows a week, bringing in local comics and outside talent. Ferrell also got the chance to help develop local comics while running the club.

“We were hitting on all cylinders,” Ferrell said. “I could run these workshops [for local talent], but it didn’t mean you were going to be on stage at the comedy club. It was an opportunity perhaps, to come up through the ranks, which is what’s missing now in Portland.”

The club closed in 2012 after a nearly 20-year run, but as Portland’s comedy scene continues to grow, Ferrell remains a constant in the equation. He thinks Portland could definitely support a full-time club again, but what it takes to run one is enormous.

“I guarantee you, somebody’s eventually gonna do it — and they will win. They’re gonna come out on top,” he said.

Now, more than a decade later, Portland still lacks a dedicated comedy club, though some groups are hosting recurring spaces for it, in spots like neighborhood breweries or established venues. 

One of those is Marcus Cardona, a Buxton-based comic who founded the Maine House of Comedy, a recurring feature night inside the Free Street Restaurant & Bar. Cardona’s operation launched in 2022, holding bi-weekly shows and weekly open mics, with the occasional pop-up night at Empire Live, the venue above the Congress Street restaurant.

Cardona and fellow comics have catered to Maine’s younger generation, with booking headliners like Gastor Almonte, who debuted his latest show “The Sugar” in New York City and Portland, and Maine comedian Lucas O’Neil, who’s set to perform in Edinburgh, Scotland in August.

The goal has been to make sure Portland has its own recognizable scene. Booking recognizable names that are “blowing up” in other cities along with Portland, according to Cardona, is one way to do that.

While Maine comics like Cardona who are setting the stage for the comedy scene to grow again in Portland, Tim Ferrell continues to cultivate local comics in the background.

Ferrell remains present for local comics seeking guidance. His next seven-week comedy workshop begins September 25 at the Hutchins School in South Portland, with another storytelling one on the way too.

He’s not selling the career itself — because “that’s insane” — but Portland is a good place to test the waters.

On top of all that, he and two other comedians are working on a show which they’ve jokingly labeled “Project X.” It’s been in the works for three years and he’s incredibly excited about it, but Ferrell said there wasn’t anymore he could share on that just yet.

“I think we’re gonna make a couple of theaters fight over it,” he said with a laugh.














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