Comedian Jamie Lissow On His Career, Working With Legends, & His Upcoming Shows At The Comedy Castle

Comedian Jamie Lissow is coming to Mark Ridley's Comedy Castle for a weekend of laughs on April 24th, 25th, and 26th. He was nice enough to hop on Zoom and speak with me a couple of weeks back.

It's been a while since he's played the famous local venue, and he's excited to get back after selling it out the last time around. "And so we decided to come back and do a weekend. But before that show last year, I probably had not been there in about 15 years. But absolutely legendary club if you talk to comedians."

Yes, he'll have two shows each day. "So I think it's like 7 and 9, which I'll be honest with you, a little bit late for me these days. I've been doing the earlier shows. I just did Naples, Florida. They do a midnight show at 6 p.m."

And, yes, Jamie does live in Alaska. I had to ask him how he manages his career from so far away. "I honestly ask myself that question every 30 minutes or so. And it's not the easiest. It's an ex-wife situation. She's from there." He says they co-parent and are in constant contact. "I still talk to my ex-wife all the time. She actually texted me right before I came on with you. I'm not even kidding. It says, F you!"

Jamie's personal life is a big part of his stand-up routine. But as he explained to me, each year he creates a different show. " So I do, I do like a new hour year to year, depending on where I am with my life. Like last year was like the divorced dad, a little more bitter, making fun of my ex. This is more about like blending families and kids and stuff.
But I would say every show, even if you came to two shows in the same weekend at, uh, Comedy Castle, they won't be the same. That's for sure."

Jamie grew up outside of Rochester, N.Y., "I tried standup in Rochester, and then I went to the University of Buffalo law school for two weeks. And I dropped out to try comedy." It was an idea his dad was behind. "I remember when I decided to drop out, I talked to my dad about this, he was like reading the newspaper, and I go, dad, I go, I'm thinking about dropping out of law school for at least a year and trying standup comedy. And he puts the newspaper down, and he goes, "I love this idea. I love this idea". And he drove me to school and got all my stuff. And I, I think back on that. And I think that's terrible parenting!"

He hasn't looked back, playing comedy festivals and night-time comedy shows like Jay Leno. Some don't know, but those shows are very restrictive of what jokes the comedians tell. "Not only that, back then you had to, they would ascribe your set, like every single word, and they would go, don't say this word, say this word instead. It's all very not fun." He went on, "Like they want to make sure like it worked everywhere at five at night, at 10 at night. They, they had me running at all these different places to make sure, like, it would get a laugh in front of everybody. And then they do that running up to your set. You do about two weeks of that."

Jamie has had the chance to work with comics and radio legends throughout his career. From working with Brother Wease, the king of Rochester, New York radio, to guys like Norm McDonald, Rob Schneider, Adam Sandler, and more. In the interview, he told some great stories about these guys. Watch above.

Go see Jamie this April at the Comedy Castle in Royal Oak. "If people want to get tickets, I know my name is not a household name. So if you want to go to, um, my website is a Rob Schneider's friend.com."

Actually, you can click the link here.