Eddie Pepitone on Denver, a Comic's Comedy and Finding Despair in Success

Eddie Pepitone is a hero to a certain stripe of comedy nerd, so his debut in the Mile High City would be newsworthy on its own. But rather than appearing at a club or theater, he's headlining a local showcase produced by homegrown Denver comics Matt Monroe and Stephen Agyei. Monroe may now divide his time between Denver and Portland, but he intends to return to town every month to co-host the show, which often sells out weeks in advance. The April lineup includes Michelle Biloon (Chelsea Lately) and Colorado favorite John "Hippieman" Novosad opening for the Underground Comedy show's biggest guest to date. With a lengthy IMDB resume that includes appearances in comedy classics such as Conan, Chapelle's Show, Old School and Bob's Burgers, Eddie Pepitone also has a new special, In Ruins, that sprinkles moments of cathartic hilarity into an apoplectic doomsday sermon. It's little wonder, then, that the documentary Pepitone inspired is called The Bitter Buddha, and that his fan base sometimes borders on the devotional. Westword caught up with Pepitone in advance of the April 29 show to discuss his impressions of the Denver scene as a first-time visitor, his status as a comic's comic, and his ability to find despair in success.

Westword: This show marks your first visit to Denver. What impressions, if any, do you have of the local comedy scene?

Eddie Pepitone: My impression of the Denver comedy scene is just word of mouth. And the buzz is that it's really a great city with great audiences, maybe the best in the country right now. Hungry for comedy and not yet jaded.

You're appearing on shows produced by Denver-based comedians; was that a deliberate move on your end or just happenstance?

Matt Monroe contacted me, so it was happenstance. But I've always been connected more to comics than clubs. I'm a comedian that comedians remember! Ha!

Where do you like to go to work out new material?

Honestly, the warmer the audience, the better. When I have a more accepting and giving audience, that is when new material happens. I work out new material anywhere I feel like people are ready for it. New material is about trusting yourself, trusting that you can talk about your latest thoughts.

How do those initial rants take shape to the point where they're ready for an album or special?

Basically, the rants come out as accumulated rage, and if the audience really responds the first time I do it, I know I have a winner. Then I keep doing it and add on to it and tweak it, and then it's ready to be recorded.

Are you working toward a new special now?

I am working out like a nag with an eye toward a new special right now. It's been a bit of a slow process because I've been so busy. I guess that's good, but a special needs focus, so I'm devoting the second half of the year to recording one. I'll probably rent out a theater for four nights and go nuts on stage and take the best of. I like to improvise a lot, and if I set up a chunk of time to do it, I believe I will have plenty for a special.

Throughout your career, you've eschewed easy laughs and frivolous premises. How do you strike a balance between rigorous honesty and punchline structure?

That's a great question. Honesty drives my standup, so I err on that side. I feel the punchline is life itself: The more honest I am, the more the intrinsic absurdity of life comes out. Again, it's about trusting that honesty will lead to the funny.

What makes you abandon a new joke? Do you remember anything in particular that you just couldn't make work for an audience?

I'll abandon something I believe in when it fails for like the seventh time. Then I'll be like, okay, it's just not funny.

The Long Shot Podcast is still going strong. Do you think that the heyday of podcasts is beginning to taper off? What's your take on the current state of the podcast marketplace?

Long live Long Shot! I think the podcast market is glutted, sure, but it's still a great place to be. You just have to know who and what you're looking for. No matter what, podcasts will still be a great thing for any artist who wants to produce unedited content.

You've been the subject of a documentary, your specials are gospel to a certain stripe of comedy nerd, and your imdb page is essentially a "greatest hits" collection of film and television comedy. Does success diminish some of the innate despair that fuels your act?

No, success engenders more despair. You keep wanting to get better also. There really is never a finish line as an artist. It just morphs into different things. It's a great challenge to stay relevant.

Do you have any projects in the works that you want to plug here?

I will be doing a nice part in a Netflix movie written and starring Jeff Garlin. Filming that at the end it the month! 

Doors open at 7 for the 8 p.m. show on Friday, April 29, at the Soiled Dove Underground; admission is $10 via TicketFly.