The first time Derek Kaill took the stage as a comic, he was already 36 years old.
“Ya I was nervous, I would say pretty much everyone gets nervous their first several times,” he said. “It’s so important to get expressions and timing right. When you’re really working on a joke, you have to make sure you have all the ingredients.”
A career in comedy had always been something Kaill had considered, even as a kid immersing himself in the performances of classic comedians.
“I loved stand-up comedy as a youth, George Carlin and Steve Martin were gods to me,” he explained. “They were originators and so important to the progress of comedy. They broke barriers.”
But as with most things, life can sometimes get in the way and that dream had been indefinitely put on hold. And though he had dabbled a bit here and there, it wasn’t until Big League Comedy opened in London that aspiring funny man really got his feet wet.
Taking part in the venue’s amateur nights, Kaill found himself as part of a group of guys looking to break into the business.
“We each started doing sets of five or 10 minutes, whatever they’d give us there, in front of a crowd of between 20 and 40 people,” he remembered. “About 10 or 12 of us got really into it and we thought — hey, this is really great to have somewhere giving us the opportunity to do this.”
Unfortunately, it didn’t last.
“In less than two years the club shut down and there were all these people used to being on stage at least once a month, some guys were doing it every week,” said Kaill. “So four of us got together at Victoria Park to talk about what we were going to do.”
They called themselves the Offenders of Comedy, a group of guys trying to make their own way, approaching local bars in an attempt to just get a foot in the door.
“We were pretty green at the time,” Kaill said with a laugh. “So we decided to do it together, since we had no idea what we were doing.”
The group scored a two-show slot at the Roxbury, and continued to chip away, one show after the other. But when Kaill scored himself a regular spot at Wit’s End Pub, things started to change.
“The other guys told me to go it on my own, and I started doing shows there,” he said. “But I wanted to bring in big names. I’d have a Toronto act come in and do 45 minutes, supported by the Offenders of Comedy. The guy at Wit’s End asked me to start putting shows together regularly.”
These days, after a much-needed shift in careers, Kaill produces, books and promotes comedy shows at various bars and theatres across the Forest City under the moniker Dr. Feelfunny.
Besides promoting his monthly comedy show at the Grinning Gator, Kaill has brought some big names to London, including Ari Shaffir and Gilbert Gottfried.
"Shaffir was way beyond anything I had done before in terms of success. I took that money and put it into bringing Gilbert Gottfried to the London Music Hall. We had over 400 people, so it was also very successful.”
Hoping to continue to build on that success Kaill’s next big headliner, Andy Kindler, takes over the Roxbury stage on Sunday, Oct. 4. “He’s a really big deal,” said the promoter of the Everybody Loves Raymond and Bob's Burgers alum. “It’s going to be a really big show.”
Though Kaill still performs at the occasional roast, the doctor is content away from the spotlight. What started out as a hobby, and a way to get some amateur stage time, had turned into a full-time job.
“I’ve just had so much fun with it,” said Kaill. “I really like the work of getting out there and talking to people. I’m doing what I love.”