Comedian Tommy Brennan proves you don’t need to have a horrible childhood to be funny

By Erin Kalejs

While comedian Tommy Brennan may look like the spitting image of a midwestern boy next door, his comedy both cleverly plays upon this image and transcends it. His standup is notable for poking fun at midwestern life and sharing crazy stories about growing up in a large family that included six sisters.

Back in 2017, he luckily managed to escape the everyday boredom of his corporate sales job to instead pursue his passion for comedy.

While Brennan was telling me about the risk he took I couldn’t help but think of a quote from the inimitable comic Jim Carrey, “you can fail at what you don’t want, so you might as well take a chance on doing what you love.”

From the first moment Brennan got up on stage and started performing improv and stand up in Chicago he “fell in love with it” and instantly knew “there was no looking back.”

In the first episode of The Curve Magazine’s new podcast, Small Talk, Brennan candidly spoke to me about his worst gig, the inspiration behind his podcast and sketch show; ‘Roommates in Law‘ which he created with fellow comic Tim Smith.

We also discussed his life changing relationship with his mentor and friend, the late and legendary comic Louie Anderson. A lightly edited transcript from a portion of our conversation follows.

The Curve: Were you a funny kid growing up, when did you realise you were funny?

Tommy Brennan: I was definitely an attention whore as a kid, but I wasn’t always the funny guy. I forget who it is who says this quote but like “the comedian isn’t the class clown, it’s the person who puts the class clown up to it.”

So it’s not the guy who streaks on the field but it’s the guy who convinces him to do it.

I would say I played more that role, I wasn’t the kid making fart noises in class and that kind of stuff but I really loved being the centre of attention and performing.

I really loved school plays and all live entertainment and that has been true for as long as I can remember.

There was something about seeing any sort of show, I loved going to stuff like that because I think a piece of me knew ‘I gotta be doing something like that!’

TC: When doing stand up you’re obviously getting a live audience reaction and therefore improvising and not always sticking to your script. However, do you think stand up comedy is a form of acting?

Tommy: Well, there’s an element of acting within stand up. There’s a reason why stand up comics call their performance their “act” because it is an act.

It’s a lot less scripted than doing a play but it is pretty scripted and you of course react to what’s happening with the audience.

It also depends on the comic. Some comics are pretty dry, they just have their set up and punch line so a lot of comics are reliant on fully acting out a “bit.”

For me, there’s definitely some acting required in my act but it’s nothing crazy but yeah you’re doing a version of yourself up there.

Brennan and hilarious fellow comic Kelsey Cook, who he regularly tours with.

TC: So then would you primarily consider yourself an actor or comedian?

Tommy: Comedian, for sure! Ideally I would love a mix of the two, acting is such a fun way to pay the bills and the acting can help the stand up and sell tickets and allow you to tour.

So I would love to do both and from the performance side I really do miss acting but I also do a lot of sketch comedy which scratches that itch.

Definitely later on down the road, I would love to get back into acting.

TC: What do you prefer doing, stand up or sketch comedy if you could only do one?

Tommy: Stand up, but sketch comedy was my way into stand up. I was doing sketch comedy first in improv through Second City and what I didn’t love about it was I was impatient about relying on other people to rehearse or plan a show.

With stand up you can go and do it every night, multiple times a night so I really like that it’s on you and no one can take it away.

Doing stand up is a skill I’ve developed over the last six years and not a lot of people can say that they’ve done that.

TC: What was the inspiration behind your podcast/sketch show “Roommates in Law”

Tommy: That came out of being bored during the pandemic.

Tim and I were both in Chicago, living about six blocks away from each other and took a virtual acting class together and started riffing on some ideas that we could film together. 

The first idea was just one sketch, we didn’t have any ideas about starting a web series right away. I would go over to his house and we would riff, drink and talk for hours and come up with some more ideas.

Finally we were like “let’s film some of these and come up with a web series.” 

The first few weeks we shot three or four of them and only used one of them because they were so bad at first, we just didn’t know what we were doing. We just had so much free time to make it better.

That was the beauty of the pandemic even though it was so horrible for most people but that was a huge silver lining, being able to sit down and make something. 

“I had a really big insecurity about starting stand up because I thought I didn’t have a hard enough life to be a stand up comedian. I had this illusion that all stand up comedians have horrific childhoods.”

TC: Who are your biggest comedic influences?

Tommy: John Mulaney is my idol. I saw him live for the first time at a pivotal moment where I had just started doing stand up but was still mostly doing improv and sketch.

I had a really big insecurity about starting stand up because I thought I didn’t have a hard enough life to be a stand up comedian.

I had this illusion that all stand up comedians have horrific childhoods and seeing Mulaney at that time come up with this hour of comedy about his life and he had a good childhood, but I was still crying with laughter.

I realised you don’t have to be some really messed up person to be able to do this and that changed my perspective.

My other big influences are comedians who are huge now but kind of came up when I was starting out, like Joe List, Sam Morril, Taylor Tomlinson, Kelsey Cook is another comic I really love and get to tour with.

TC: You first met the late Louie Anderson when you were hosting a show for him back in 2019, at the Chicago Improv Club and he eventually became your mentor and friend. What was the best advice he ever gave you?

Tommy: Louie was such a good mentor to me. It was amazing, sometimes I forget how cool that was, that I got to become friends with him at that point in his life. It was a great four year friendship and I think about him a lot.

The best advice he gave me was to write about yourself. He used to make me do this thing where he would tell me to journal three pages about a memory or time in my life, like any starting point and then just write.

I have a 60 page word document and it’s called “Louie’s Thing” and it’s just random memories that I’ve written two or three pages about.

We would hop on the phone and I would read through it with him he’d tell me what he thought was funny. 

He knew that a joke about yourself or your family was timeless and no one else can tell it, that was his big thing.

He also always used to tell me “you need to be bombing more!” Because he was a firm believer in if you’re not bombing enough it means you’re not trying enough.

Brennan posing with Louie Anderson at the Chicago Improv Club on the night they first met.

For much more with Brennan, including how he deals with hecklers, listen to the full episode.

To hear more in depth interviews with fascinating people from the world of arts and entertainment— from actors and directors to artists — check out Small Talk on Spotify.

You can follow Brennan’s comedy here:

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