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An Interview with David Montgomery

Updated: Apr 16, 2019

David Montgomery's comedy is a rare mix of snark and heart. The stand-up comedian weaves in uplifting anecdotes about his first grade teaching job and poignant tales of his troubled childhood into his self deprecating routines. It's no surprise his imaginative style has earned him several Moth Storyslam wins-- his humor stems from the specific but has universal relatability. It's a winning combination of personal narratives with sarcastic undertones drawing on experiences we've all had, and genuinely raw observations about the resiliency of the human spirit. His podcast, 2 Gays, No Girls, At A Pizza Place used the same approach applied to a different medium, offering punchy yet well-mannered interviews strung together by rip-roaring reflections on life. Although I was originally intrigued by the ironic tone of David's work, I stayed for its powerful testament to human connection, and the healing power of the Spice Girls, duh.

What work are you most proud of?

It sounds silly, but the first solo show I ever did really meant a lot to me. I did it for the fringe Festival in Pittsburgh a few years ago called “How the Queen Found His Crown” and won some awards for it. I remember when I found out that I got the slot to perform, and I was so excited. Then I realize that I have to write an hour long solo show, and memorize it, and perform it!  It came together so much more quickly than I thought it would, because I have done so much separate work with storytelling already. It was just about piecing some of the stories together and finding an appropriate emotional arc.  I received the most stunning feedback from strangers on the show, and I found that to be really healing. It helped me as a writer and as a performer in the long run, realizing that if I can have a real emotional through line to the audience, rather than only being funny, it has a more lasting and meaningful impression on people.

How did you get your start in comedy?

I always wrote just for fun, as a creative outlet. I’ve always been a consumer of comedy, but never shared it with anybody. I was teaching first grade for a very long time. And then one day a stranger asked me to do a storytelling show, and it was in front of 30 people. And I was sick to my stomach all day long about it. I kept thinking, what if they don’t like me? What if they boo? What if they don’t laugh?

Thankfully, it went pretty well. And I was recommended to put my name in the hat for the open mic version of a storytelling show called The Moth. I didn’t know was a competition until the host started telling the audience the rules of the show. And I panicked a little. I ended up winning that first night with a story and had to deal with my family and my career. I found it really validating right away. Slowly but surely I realize that my specific voice in comedy was most present when I was telling my own truth.

I write some fiction, but the majority of my paperwork comes through comedic storytelling.

What projects are you working on right now? Too many to count! I’m recording a live album due out in 2019 called “David Montgomery: queen of small town gossip.“ and I just put the finishing touches on my memoir. I hope that gets to come out in 2019. There are a couple of TV and movie projects that I can’t quite talk about just yet. But exciting things are coming in the new year!

What advice would you give to your younger self?

You are worth it. Don’t listen to one negative person. You are great and you are worthy of love.

Who are your inspirations?

Tina Fey is a God. Jerry Seinfeld broke the mold for a lot of the comedy that we see on television today. Amy Poehler is the improv genius. Paul F Tompkins and Scott Aukerman are two of the weirdest and funniest people are alive on the planet today. There are so many up-and-coming talent that I see a lot in Los Angeles that are destined for great mess as well. Hillary Matthews Was part of an ensemble that didn’t show called “best friends club” that was possibly the most inspiring 30 minutes of live comedy I’ve seen in years.

How would you describe your comedy? Silly, self-deprecating, sarcastic, and true.

What are your plans for the future?

I think my most immediate one is making sure that this upcoming memoir is a huge success. I’m still shopping it to publishers at the moment, but keep your eyes peeled for “Here’s the Story from A to Z.” 

Images used in collage via @buymeahotdog


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