Jimmy O’Brien on Making Funny Sports Videos, Not Being a Talk-Radio Blowhard and Why He’s a Proud Mama’s Boy

Jimmy O’Brien on Making Funny Sports Videos, Not Being a Talk-Radio Blowhard and Why He’s a Proud Mama’s Boy

I don’t like that (bad fans) are doing that, and then I don’t like that other people are allowing these 10 people to change the narrative on 40,000 people. If I have a voice and I can be someone that says, “This isn’t cool,” and I know a million people are going to watch, then I’ll grandstand that one time for that. Otherwise, I try to stay off my pedestal.

Are there certain players you think are especially funny?

Funny on purpose, or just funny to watch? Like, DJ LeMahieu is hilarious — it’s not on purpose. He’s just so intense and so boring in his answers that it cracks me up. They do those things where the Yankees players walk (into) spring training, and there’s a question on a whiteboard: “What’s your favorite Taylor Swift song?” And they all answer it. But DJ’s not appeared in one of them, or he just walks past silently — that’s hilarious. 

I think there’s some players out there that, physically, doing what they’re doing — Bartolo Colon swinging a bat, that’s hilarious. But on purpose being funny, I don’t think they get the avenue to do that much or to have a voice. Joey Votto is funny. I like when he throws the ball into the crowd, but doesn’t actually throw it, fakes them out. It’s fun when you can have a sense of humor and play with the crowd in those ways.

As Jomboy continues to grow, do you think of yourself as the face of this company? “What persona am I projecting? How do I represent this brand?”

I always say I have a lot of trouble not being me. I’m a shy person if you don’t know me. My wife got pretty frustrated the first time we hung out with her family and friends, ‘cause I was shy, and she was like, “What?” I’m like, “Oh, I guess you don’t know that about me.” I’m a wallflower in scenarios where I’m not around people I know really well. 

I try to be consistent in who I am on mic because that’s probably the best version of me — I’m more trying to be lighthearted and easygoing and stress-free. I’m not always stress-free — especially these days with the company and all that — but we’re not doing characters, we’re not being someone we’re not. It’s pretty nice to go into this interview — or a business meeting or hiring someone or on a mic — and I don’t have to think about, “Oh wait, get in the zone — you got to do this now.” It’s just who I am. We made it easy for ourselves that way.

A lot of sports media is built on “takes.” You don’t really do that.

That was bizarre to me when I would share a thought — people (would) respond, “That’s a bad take.” And I’m like, “Oh, I don’t even know if I stand by it — I was just thinking out loud to you guys here.” But because everyone wants everything to be a take that they can either disagree with or agree with — call you dumb or not — you’re not allowed to have thoughts anymore. Everything has to be stamped “final,” that’s your opinion. I’m like, “Wait, hold up, I just think, ‘Are the Rangers going to be good this year?’” I’m working through it in my head out loud on the show, or I’m just tweeting. 

Clearly, many on-air personalities have figured out that being loud and opinionated generates attention. 

I think it’s incredibly impressive to be able to formulate strong opinions on everything. I’m an opinionated person — growing up, people know, I’ll try to find my thought on something if you ask me. But yeah, some of those shows, do they really believe that? Or they just half-believe it and they’re hiding it? But the conviction in which they say it — and for every topic every day — I’m like, “Yes, it’s impressive.” Try to do it — you will get exhausted so quickly. 

Sign up for the Cracked Newsletter

Get the best of Cracked sent directly to your inbox!


Switch & Save With Liberty Mutual.

Share This Article