Kansas City Entertainment

Move over, Jason Sudeikis? Up and coming KC comedian is hosting charity show of his own

Caleb Hearon will never be confused with Jason Sudeikis (although Josh Gad is another matter). But there are some remarkable similarities between their careers.

Like Ted Lasso himself, Hearon is a funny guy who got his start in professional comedy doing improv in Chicago and who now writes and stars on TV shows and in movies. Moreover, like Sudeikis, he is proud of his ties to Kansas City, is a huge Chiefs fan and uses his talents to give back to the community.

Sudeikis has his annual Big Slick and Thundergong! charity events, and Hearon has followed suit with Yeehaw. He serves as emcee for the variety show, a benefit for Kansas City Tenants. The 2024 show is Saturday, Nov. 23, at the Midland.

“It will be a big fun night of music and comedy and being with the community,” Hearon said in a recent phone interview. “It’s nice that I get to do the thing I love, and it helps me to do something that actually matters.”

This is the third year for Yeehaw, which he and friends started as a last-minute gathering at The Ship before moving to The Truman last year and now to the Midland.

Hearon grew up in Chillicothe and Brookfield in northeast Missouri, then attended Missouri State University, where he belonged to a fraternity and was even its homecoming king candidate one year.

“It was as hilarious as you would imagine,” Hearon said. “But I had a good time.”

He found comedy at Missouri State, joining an improv club. From there, it was onto Chicago, then Los Angeles and now New York, all while maintaining roots in Kansas City. His mother lives here, and he got his own place a couple of years ago.

“I pretty much split my time between there and New York,” he said.

What started as a comedy career — he had a tryout for “Saturday Night Live” in 2019, and Variety named him one of its “Top Comics to Watch” in 2020 — has blossomed into an acting career. You might have seen him in small roles in the TV shows “Mr. & Mrs. Smith” or “Fargo” (Season 4, Episode 4 during the 2020 season set in Kansas City) or the movie “Jurassic World Dominion.”

“It’s pretty cool,” Hearon said. “I started doing improv in college, and then was doing stand-up and characters and stuff in Chicago. I didn’t study acting or theater or anything growing up, so I just walk into getting to act, and it’s such a fun thing to do.”

Now he has what could be a breakout part in the Max movie “Sweethearts,” a rom-com premiering on Thanksgiving, Nov. 28, about two college freshmen who make a pact to break up with their high school sweethearts over Thanksgiving break.

Hearon, who is gay, plays the gay best friend of the lead characters.

You don’t need to remind him that the gay best friend is an almost required element of 21st century rom-coms. Even he can joke about it, which he did at the movie’s world premiere earlier this month in Georgia.

“One of the co-writers of the movie, a really sweet guy and really talented writer, he laughed at the joke and then he was like, ‘But I think we wrote the character with some depth, right?’” Hearon said, laughing. “It’s not a dirty phrase to me. I like the gay best friend.”

He almost didn’t play this one, however, because the character is a college freshman and he is a decade removed from that time in his life. Hearon said he got in “just under the wire” to play a teenager — he won’t turn 30 until January.

“I originally refused to audition for it because it said a teenager, and I was like ‘Let’s not waste anybody’s time.’ I look my age,” said Hearon, who praised the movie’s makeup artists.

“Hopefully, it’s close to passing. But they tell me it doesn’t really matter in movies. I’m hopeful people online aren’t too mean to me about it.”

Meanwhile, he is starting to get recognized more often, even if some people mistake him for actor/singer Josh Gad of “Frozen” fame.

“People do think I’m Josh sometimes, which is a compliment,” he said.

One of those people was a door man at Largo, a comedy spot in Los Angeles.

“I walked up, and … I say, ‘Hey, man, I’m on the list. I need to grab my ticket.’ And he goes, ‘Oh, I got you. Gad, right? Josh Gad?’ And I was like, ‘Brother, my bank account wishes, but no.’”

Hearon is doing OK in his own right, however.

In addition to writing for the animated Netflix series “Human Resources,” he hosts the podcast “So True with Caleb Hearon” and has several other projects in the works. They include the Missouri-set movie “Trash Mountain,” which is loosely based on his experiences after his father died. Hearon, who wrote it and aims to play the lead character, said he hopes to make “Trash Mountain” in 2025.

“That’s all fun and good,” he said. “But the real treat genuinely is to get to do stuff like the benefit for KC Tenants and to get to give back to a place that I care a lot about.”

When and where is Yeehaw?

Doors will open at 7 p.m. Friday, Nov. 23, with the show scheduled to start at 8 p.m. at The Midland, 1228 Main St.

Who will perform?

Caleb Hearon and Katie Crutchfield, the Alabama-born and Kansas City-based singer-songwriter who performs as Waxahatchee, will host. Other musical acts appearing will be Briston Maroney, Samia and The Salvation Choir, along with comedians Jay Jergen and Beth Stelling.

Who does Yeehaw benefit?

Kansas City Tenants, which supports renters and working-class people in the city

How much does it cost?

Tickets are $30-$60.

Where can I get more information?

midlandkc.com

Dan Kelly
The Kansas City Star
Dan Kelly has been covering entertainment and arts news at The Star since 2009. He previously worked at the Columbia Daily Tribune, The Miami Herald and The Louisville Courier-Journal. He also was on the University of Missouri School of Journalism faculty for six years, and he has written two books, most recently “The Girl with the Agate Eyes: The Untold Story of Mattie Howard, Kansas City’s Queen of the Underworld.”
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