Standup comedian probably isn't the first profession that comes to mind when you see Cy Amundson. On the surface, the 27-year-old Acme regular looks more like the self-assured jock you used to brush by every morning in high school rather than the late-night funnyman that had you convulsing with laughter the night before.
Of course, even standup comedy has its exceptions.
Over the last six years, Amundson's uncanny penchant for joke writing, coupled with his affable stage persona, has made him one of the most gifted and successful fixtures in the Minneapolis comedy scene.
The Worthington, MN, native will be making his television debut tonight with an appearance on TBS's Conan. Cy Amundson recently took a moment to talk with City Pages about Conan O'Brien, his recent success, and why comedy doesn't have to come from tragedy.
A lot of the comics coming up today were raised on guys like Conan O'Brien. Is he someone you idolized at a young age?
You know, I grew up watching Letterman. One of my earliest comedy memories is of Chris Elliott on Letterman. He'd do all these characters and all this ridiculous stuff. My older brother and I would stay up and watch Letterman, and that was one of the first things I remember thinking was really funny. Now, he's one of the guests on the night that I'm on Conan, so I'm losing my shit about that a little bit.
As I got older and actually started to develop a sense of humor of my own, then of course I was into Conan. The great thing about him is his willingness to do anything and everything regardless of how it might look. There seems to be no fear with the things they do on that show, and I love that.
Do you remember what prompted you to pursue standup?
When you grow up in small town Minnesota you don't conceptualize that as a real career possibility. You don't know anyone who's done it. You're just so far removed from it. My family members are all farmers and teachers, all hard working blue-collar types.
When I moved to the cities, I was living with my sister and my brother-in-law John really pushed me to try standup. I had done some sketch stuff, but he knew how much I liked comedy and standup. He pushed me about the Funniest Person in the Twin Cities contest that Acme runs, and kind of forced me into the contest. I went down and I did a set. It didn't go great, but I was hooked from there.
Were your parents supportive early on or has it taken a while for them to get on board?
I did get a degree, so I had a back-up plan. I was very rational about it. Like, I always said that if by  I didn't see this being a legitimate career possibility, then I would hang it up and use my education. But from pretty much day one my entire family has been super supportive -- which is crazy for a comic.
Do you still find yourself questioning your career?
Things have started to go really, really well the last couple of years. I can definitely see a possibility of it going where I want it to go, but I think everyone questions it. Standup is wonderfully rewarding, but it's also a difficult career. Nobody wants to sit in Toledo, OH, on a Saturday night when all their friends are back home having fun together.
Your career took off pretty quickly. Did you ever feel intimidated at any point? Did you ever feel like things were moving too fast?
No. That might sound cocky and dick-ish but in the comedy community I was raised in at Acme I've learned to be more than ready. I was always working my ass off in case the cards started to fall in order.
A guy I learned a lot from is a local comic named Mike Brody. Mike told me very early on to take everything you get -- don't be cocky or anything like that -- but expect your success. That doesn't mean you have to be an asshole about it, but if you expect your success, then you're driven to work hard for it and you won't be intimidated when it comes. I come from a sports background, so I love this shit. I love the pressure and all that.
Do you think the high-pressure environment that comes with being an athlete helped prepare you for standup?
When I started doing standup full time, I had to give up basketball because I had started a coaching career in the cities. Basketball was a pretty huge part of my life, and that whole preparation and competition aspect of that world has prepared me immensely for the standup world -- and anything else that I choose to do. There is a lot of pressure in standup and acting, but when you're used to that you kind of enjoy it.
The preconception people generally have about comics is that they're all saddled with personal problems. But on the surface, you don't seem to fit that bill. Have you ever feel out of place because of this?
I'm one of five non-drinking, non-drug addicted comics that have ever existed. I didn't ever have a problem with it; it's just a choice I made early on. I've been given shit about it a bunch of times, but there's a number of people who have their shit together. I wouldn't say I feel out of place because I'm pretty confident in myself.
I remember when I first started doing comedy, Darlene Westgor followed me onstage -- I was hosting -- and she walked up and said, 'Keep it going for Cy Amundson. Look at him, most of us comics are all screwed up. Cy, what the fuck are you doing comedy for? Get out of here.' I love Darlene with all my heart, and she's been a very positive influence. But this idea that comedy has to come from a specific place -- I've never bought into that.
So you reject the idea that it's a pre-requisite.
I think comedy can come from so many different places. You can have the lovable loser, you can have the cocky but likable winner, you can have someone whose been through everything. And then there's guys like Brian Reagan, who is one of the best standups of all time, and he's just fun and silly. Comedy doesn't have to come from guys spinning the propeller on their beanie, but it also doesn't have to come from the depths of depression either. I respect people if that's their process, but I think it can come from all different angles.
Check out the clip below: