The Art of the Punchline
Behind the Scenes with LA Comedian Courtney Cronin
If you’ve ever seen comedian Courtney Cronin perform, you know this much.
She has the funny gene.
She sees humor, sometimes clean, sometimes not so clean, in just about everything.
This isn’t a new development.
It’s something she says she discovered very early on.
“I guess, like most comedians, I was a goofy, nerdy kid,” says Cronin. “I was always drawn to comedy.”
“When I was younger, at sleepovers, my girlfriends would want to rent rom-coms and things like that. I wanted to rent comedy specials. I was watching comedy, and I always thought it was so hard. I wondered, ‘How do they come up with that?’”
But unlike many comics who describe themselves as class clowns, Courtney says her humor came more from curiosity and an endless fascination with the people around her.
“I’ve always enjoyed that connection, I guess. I’m chatty. I like connecting with people.”
Her father recently reminded her that she’d been doing exactly that since she first started forming complete sentences.
“I would be two years old and just talking to people all the time.”
Comedy wasn’t necessarily the goal at first.
In fact, it almost happened by accident.
At age 13, there was an acting competition.
Yep.
An acting “competition.”
There was only one problem.
She needed a comedy monologue for the audition.
“I was like, ‘Oh my God, I don’t know where to find a monologue.’ So I wrote one.”
She apparently wrote a really good one.
The judges loved it.
Before she knew it, she was competing in comedy categories throughout high school.
“That’s how it all kind of got rolling.”
Courtney Behind the Curtain
During my recent 40-plus-minute conversation with Courtney, I quickly discovered that the Boston-born comedy writer, stand-up comic, and Emmy-nominated television writer definitely loves comedy, but she doesn’t have to be front and center on stage to find joy in it.
She’s perfectly content behind the scenes helping others shine.
She spends hours crafting jokes, sharpening punchlines, and helping everyone from television hosts and comedians to rock stars find their funny.
She’s written for comedy veterans like Wayne Brady, Chelsea Handler, Jay Mohr, Ken Jeong, Dee Snider, Donald Faison, and dozens more.
She’s also written jokes for the likes of Chet Roberts of 3 Doors Down fame and Raelyn Nelson—yes, Willie Nelson’s granddaughter—for her popular passion project known as Punchlines & Backlines, a live show where rock musicians attempt stand-up comedy for the first time.
The concept grew out of an uncomfortable experience while producing celebrity roasts.
After witnessing one performer leave a comedy roast genuinely hurt, Courtney began wondering if there was a better way.
“How do we make this as fun as a roast, with the jokes and everything... but not mean?”
The answer became a format where musicians could tell stories, share personal experiences, and connect with fans through comedy.
Cronin laughed when talking about how she and Don Jamieson helped Chet Roberts bring a funny story to life with punchy lines about the time Chet literally messed his pants but still posed for photos with fans before heading back to his hotel room to change.
“Chet gave us so much to work with.”
She says, “Don and I are writing partners on this, and we both agree 100% on loving a good sh*t-your-pants story. Because who cannot relate to that, whether they want to admit it or not?
“And it’s funny. We joke that in your 20s, sh*tting your pants is mortifying and horrible, but in your 50s, it’s a minor inconvenience.
“We had so much fun coming up with all the stupid ways to say ‘sh*t your pants.’ We were like, ‘Shart my shorts,’ and ‘I got a dingle dangler in my Wranglers!’ ‘3 Doors Brown!’
Having been in the crowd that night, believe me when I say those lines hit hard.
The Punchlines & Backlines show has become a staple of the Monsters of Rock Cruise and continues to expand across the country.
“We used to have to beg people to do the show.”
Not anymore.
“I have to thank Kip Winger for that,” says Cronin. “Because Kip agreed to do the show early on. Once people saw that Kip said yes and that he trusted us, people were like, ‘Oh, I want to do it!’”
Courtney has worked on more than 45 television pilots and countless comedy projects, yet she still talks about comedy the way a fan talks about their favorite band.
Like many aspiring entertainers in LA, Courtney has more than paid her dues.
The road to her writing career included countless hours waiting tables.
Lots of them.
“I waited tables for a really long time,” she said. “I worked during the day. I did comedy four or five nights a week.”
For six years, she balanced work and comedy before landing her first professional writing job at age 28.
“I’ve been writing professionally ever since.”
Ask Courtney about her favorite writing accomplishment, and she doesn’t hesitate.
The answer comes immediately.
“I got to write a sketch for Kermit and Miss Piggy with Wayne Brady.”
The sketch featured Miss Piggy, Kermit, and Wayne Brady performing “Brick House.”
What made it even sweeter?
“It’s one of the only scripts I’ve ever gotten back that said, ‘No notes.’”
She still has it framed.
“No notes,” she says. “That never happens.”
Monsters of Rock Cruise
I asked Courtney to tell me more about the Monsters of Rock Cruise, and I’m glad I did.
She calls it “the most glorious event.”
She lights up when discussing it.
“It’s like all those things we loved as young people. All those posters on our wall have come together on one boat.”
She believes it’s impossible for music fans to fully appreciate the cruise until they’ve experienced it themselves.
“All those concerts we traveled around to see for 20 years are all in one place.”
The cruise has also become the perfect environment for her comedy shows.
“The audiences love deep, weird references. They love it.”
What people may not know about Courtney is how deeply she cares about the people she works with.
I mentioned that I noticed how carefully she introduced guests and how much effort she put into making first-time performers feel comfortable.
She genuinely wants every performer to succeed.
“I love the show. I want everybody to kill it.”
That generosity extends far beyond the stage.
When she talks about her friends, fellow comics, musicians, and collaborators, she leaves her ego at the door and somehow manages to fit 10 pounds of enthusiasm into a 5-pound bag.
And Then There’s Rainy
Of course, no profile of Courtney would be complete without discussing the true star of the household.
Rainy.
A rescue dog she saved from what she described as deplorable conditions.
The dog that was once brutally neglected is now the undisputed king of the castle.
She says she and her husband take Rainy kayaking and make sure his life is filled with adventure.
“It’s obscene what we do with this dog.”
Ol’ Rainy apparently has female admirers, too.
I wondered who received more attention—Rainy or her husband.
The answer didn’t take long.
“Oh, Rainy,” she deadpanned.
Toward the end of our conversation, I asked Courtney what she hopes people will say about her career ten years from now.
Her answer was straightforward and to the point.
“I hope people think that I never bullsh*tted them.”
That’s probably the simplest way to explain Courtney Cronin.
Whether she’s writing television, helping rock stars tell jokes, producing live comedy shows, or standing on stage herself, authenticity matters.
She cares.
And she wants the people she works with to know it.
“I spend weeks on my set so that people notice that I’m taking the time because I care.”
That’s no joke.
That’s who Courtney Cronin is.
Follow Courtney
“Please go to my Instagram because I need some heat, y’all,” she joked. “I am tepid as a Mofo on there.”
That may be the funniest thing she said all day.
You can find Courtney at courtneycronincomedy.com and on Instagram at @courtcrodold, where you’ll find upcoming dates, comedy appearances, Punchlines & Backlines events, and—if you’re lucky—a few photos of Rainy stealing the spotlight.