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Jimmy Flynn: Don’t Take Yourself Too Seriously

Jimmy Flynn is a natural on the radio. Before his recent graduation in June 2018, Jimmy was the editor-in-chief of The Santa Clara student newspaper, and he produced his own radio segment on KSCU, the Santa Clara student radio station. This past year, Jimmy and his friend Riley McShane created a movie titled “Ego Death: A Mockumentary Inside a Mockumentary,” which is a comedic take on their experiences running music and art events during their time at Santa Clara. In this interview, we discuss how Jimmy got started with stand-up comedy, his filmmaking process, what he’s learned from being editor at the newspaper, and his plans for a creative future.

Interview Highlights

Gavin Cosgrave: What was the inspiration for your recent movie?


Jimmy Flynn: Even though I was the editor-in-chief of the newspaper, I never really saw myself as a journalist. I always loved comedy and film above everything else. My latest movie is called “Ego Death: A Mockumentary Inside a Mockumentary,” and it’s based on the lives of myself and my friend Riley McShane who’s a musician. Together at Santa Clara, we put on seven shows called “Show Broncos” with music and comedy. We were just trying to bring arts, culture and live performance to Santa Clara.


Last year, we had the idea to make a “mockumentary” about our experiences making the show. I thought that if we did it too realistically, it would be self-indulgent, so I tried to exaggerate certain character aspects. My character is self-destructive and has bad drug problems, and Riley’s character is incredibly lazy. For purposes of comedy and drama we accentuated those.


I want a career in the filmmaking industry someday, and I figure that the best way to do that is to just start making movies. We made the movie on an iPhone 6 and I edited it with iMovie. I also wanted to show that you don’t need big-money resources to make a movie, you can just do it yourself.


GC: When did you first get into stand-up comedy? That seems like most people’s worst nightmare.


JF: I’ve always been a very performative person. A less polite way of putting it would be that I love attention. My two strengths as a person are writing and performing. I got into it about two and a half years ago and it happened through the newspaper. I interviewed a guy Dean Garcia doing stand-up on campus. He would do classroom performances in the Kennedy Commons, which they’ve torn down since. He said that I could open for him and do five minutes. We did a few shows, I met Riley McShane and I felt really good about it. Stand-up is something I’d always wanted to do.


A lot of the people I look up to are comedians. They are able to take sad situations and show them in a more humorous light, and do social commentary in a way that’s funny, and I think that’s a noble thing. If you look at it from a Jesuit perspective, you’re serving others and providing laughter. Personally, I think comedy is timeless and we’ll always need comedy.


GC: What have you learned from being the editor-in-chief at The Santa Clara newspaper?

JF: It’s definitely made my writing better. Journalism is so different from any other type of writing. It’s so punchy and to-the-point; if it’s not, no one will read it. It made me faster, more creative, and it helped other types of writing I was doing as well. It made my jokes punchier, and I would incorporate the idea of a lead, or hook. With a joke, you can say something immediately that hooks people in, then allow yourself to expand upon an idea before you hit the punch line.

Being the editor-in-chief taught me how to better relate to people, empathize and it really taught me to listen. You have to listen to and trust your employees.


GC: How did you get involved in radio?


JF: I started radio towards the end of my first year, and I didn’t want to go and play music like everyone else. I wanted to do talk radio. I was a huge Howard Stern fan as well as Marc Maron and the WTF podcast. My show was called Amateur Hour, and all my friends would come on the show. It’s an experience unlike any other. I would ask them goofy questions to try to get good stories out of them.


At one point we did a roast, and I invited all my guests to roast me. There were 25 or 30 people and they took turns taking shots at me. I’m someone who believes you should really laugh at yourself.


The one regret I had is that I wanted to set a record for the longest radio show ever and do an overnight 10-hour show that students could try to break in the future.


GC: What are your plans after graduating?


JF: This summer I’m going to be teaching a creative writing class at a summer program. I get to create my own curriculum, and I want to teach 5h and 6h graders the creative writing they wouldn’t learn in school. Maybe even how to write basic jokes. The other thing I want to emphasize is public speaking. There’s a stereotype that our generation is so involved in social media and technology that we can’t even hold a conversation. People are terrified of public speaking, so I think that’s a good lesson to learn early.


Looking forward, my goal is to move down to LA with my brother and have a career in film and television. Right now, I’m pitching to a company that works with Paramount with a TV series script we’ve written. This is what I love to do and I want to do it as long as I can.


GC: Is any part of that scary?


JF: There’s definitely an element of risk. I’ve always really enjoyed pressure, writing my own rules and dictating my own path. That’s why a career in entertainment is really attractive to me. Even people in the industry don’t really know how it work, everyone is kind of flying by the seat of their pants. Just doing something that’s creative and allows me to express myself.


One professor I had named Steven Carrol said, “You have been successful your whole life, and I know that you are sitting here right now. Just because you graduate and have a diploma, doesn’t mean you’re going to stop being successful.” I’ve always tried my best to create new stuff and be innovative, and I’m taking a bet on myself that that’s going to continue.


GC: If you could send a message to everyone in the US, what would you say?


JF: I would probably say, “listen, don’t take things too seriously, and you have to laugh at yourself.”

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