In 2021, in that weird netherspace between vaccination distribution and the widespread sense that being inside was cool again, Dylan Reiff, the Artistic Director of Kickstand Comedy was looking for a way to get Portland’s robust comedy scene back up and performing again. 

“We knew that there were opportunities to do something outside that was safe, and fun and that was hopefully something the community needed," remembers Reiff. "So we started to look around at a bunch of places and spaces, alternative venues that were outside. Parking lots, Drive-In Theaters. Thanks to the Portland Parks Department, we were able to start looking at starting a show in Laurelhurst Park.”

The first show had about seventy-five people: Respectable for a local comedy show, but not, like, obscene. Then, it grew. And grew and grew and grew to the point where, every Friday during the summer in Laurelhurst Park, there are routinely 4.000 people attending a local comedy show in a park in Southeast Portland. 

Comedy In the Park is a relatively new Portland tradition. It's an inexplicable thing in the middle of the summer—simultaneously a great opportunity to hear local artists to perform in front of an audience size that they would never even dream about, and a good excuse to whip out the picnic blanket, bring the kids—since No Cussin’ rules are in play in the park—and just get your laugh on. 

Julia Corral  Photo: Corbin Smith

“It’s kind of like a Fourth of July Parade,” says Julia Corral, a local comedian who has hosted the show for the last three years, currently co-hosting with fellow comedian Rachelle Cochran. “Now, this is what people do on Fridays in the summer.” 

A crowd of 4,000 at a comedy show can be a little stressful, but Corral thinks Portland audiences are uniquely suited to creating a good environment at a big event. 

“There’s so many activities that are this big," she said. "I feel like we have a really good etiquette on how to act. I remember the first time I went to a concert at Edgefield, and my friend was like ‘Just leave your blanket, it’s fine, no one's gonna move it,’ I was like, ‘What?’ I feel like Portland is really awesome like that. We all collectively decide to be neighbors to each other, in a friendly manner.”

Stand-up comedy is traditionally developed and performed in theaters and little dark rooms,  so it's an odd match for a gigantic park. Corral explains, “I think performing on the outside is different because the sound travels differently,” says Corral. “Usually, when you perform inside, you hear the laughs, but you don’t see the people because the lights are dimmed. But when you perform outside you see all the people, but you don’t hear the laughs.” 

Corral says she's used to it by now, but some people find it a little alien. “A lot of my job as host of the show is to really encourage people to walk around the park so they hear the laughs," she says. "Because it does shake some people, where they don’t feel like they’re being funny. But it’s just the way it’s hitting the audience.” 

“The first one I did was extremely hot,” relates Sam Whiteley, a comedian from Tualtin. “I've had better luck with the weather on the last two, but the first one was pushing triple digits. I remember being thankful to be irritated about the heat, because it took away some of the nerves of performing in front of such a vast group of people.” 

“I try not to take it for granted,” Whiteley says. “It’s cool that it's accessible to as many local comics as it is. Like, 30-45 people is a pretty good crowd for a weekly show in a bar, and it’s literally, thirty or forty times that.”

Matt Braunger Photo: Corbin Smith

Comedy in the Park remains firmly rooted in the local comedy scene, but as it's gotten bigger and bigger, a few national acts have strolled through. Sean Jordan and Kyle Kinane, national touring guys who live in the area, make it out every year or so. Ian Karmel, Portland’s favorite son, dropped by this year, along with Matt Braunger, Brandie Posey, and Ron Funches, of The Great North fame. 

Reiff is hoping to get some of that firepower for the first ever Comedy In the Park Fest, a two-day event spanning a standard show on the Friday evening of September 6 and the first-ever Saturday show on September 7. Mum’s the word on specific performers as of yet, but I did get Dylan to drop some pretty big names off the record. Whoever is there though, expect a good time, immaculate vibes, and big laughs.

Kickstand's Comedy in the Park takes place at Laurelhurst Park, SE Stark & Cesar E. Chavez, every Friday at 6 pm through Friday Sep 6, free, all ages. The first-ever Comedy in the Park Fest kicks off Sat Sept 7, 3–8 pm, free, all ages. Some material may venture into PG-13, R-rated territory.