When Jordan Klepper went into comedy, he didn’t have a backup plan.
“This was not something I necessarily planned on doing, getting into this — this world of comedy and the world of entertainment,” says the 44-year-old Kalamazoo native and correspondent for Comedy Central’s The Daily Show, “but I never had a real strong backup plan, and I wouldn’t necessarily recommend that for someone.”
Actually Klepper, a 1997 graduate of Kalamazoo Central and the Kalamazoo Area Math and Science Center (KAMSC), did have a backup plan of sorts — math. As a Heyl scholar at Kalamazoo College, Klepper was a talented STEM student with opportunities to further his studies at Yale. To Klepper, though, who wasn’t so sure about a career in math, having a scholarship allowed him to pursue a double major. After attending a performance by Monkapult, K College’s student improv group, he knew what that second major would be — theater.
“K is really a place that you can jump in and be a part of something right away,” he says. “A mild interest in theater means you are on the stage in a week.”
Looking at Klepper’s career bio might make one think that his foray into comedy was as easy. He is an alum of Chicago’s Second City improv group and New York City’s Upright Citizens Brigade and in 2014 became a regular correspondent on The Daily Show. He even had his own short-lived late-night show, The Opposition, which aired on Comedy Central after The Daily Show.
But, despite an impressive resume, Klepper says he continuously tackled doubt during his rise.
“I think the imposter syndrome is something I think we all reckon with,” he says. “The arts are something that you’re constantly questioning whether it’s the right path. A benefit I’ve always had is that the world of improv is one where you fail a lot and fail often and you get comfortable in failure.
“There was never anything that I actually wanted to do more than what I was doing, so even if there was doubt, there wasn’t an option to get off the path that I was already on and more excited about.”
Even his parents, Mark and Betse Klepper, were on board. When their son performed a Michael Jackson lip sync battle with a friend for a talent show at K College, they were in the audience.
“When he came out, the place went nuts,” recalls Mark Klepper, the comedian’s father. “He blew us away. At that point, Betse said, ‘He could do this.’ He could play a role. He could act.”
At the time of this interview, in June, the Writers Guild of America strike had hobbled the entertainment industry, putting The Daily Show on hiatus. Klepper was using the break to return to Kalamazoo for his June 30 filled-to-capacity presentation, “Celebrating Books While They Are Still Legal!” at Miller Auditorium as part of the Kalamazoo Public Library’s 150th anniversary celebration. During the program, Klepper discussed his ties to Kalamazoo, but, in keeping with his comedy persona, found humor in the news and current events.
Comedy & current events
Current events have always been a mainstay of Klepper’s comedy, from his days doing improv with The Second City to his role on The Daily Show that supercharged his career, where he covered the Trump candidacy, Trump’s subsequent presidency and its aftermath. For his regular segment, “Fingers the Pulse,” Klepper attended political rallies and events, conducting person-on-the-street interviews to get to the root of the logic behind political viewpoints.
“I love interacting with people and finding comedy and humor out of that interaction. The best thing about The Daily Show is you get to go to places and talk to real people. When Trump ran, I found sort of a sweet spot going out and talking to people about that,” he says, acknowledging that he had “a real sense of curiosity.”
“I want to know why people believe or trust some of these things this former reality show host would say. That curiosity led me (to) a place where I also got to confront people with the frustrations I had and to actually engage with people and issues face-to-face.”
Klepper says he was astonished by the ingenuity and creativity some Americans showed in their ability to create realities at the drop of a hat. He recounts an interview he did with a woman at the time of the first Trump impeachment. She says she believed the then-president’s claim that he did not pressure Ukrainian president Volodymyr Zelenskyy to launch an investigation into Democrats, including his political opponent Joe Biden and Biden’s son Hunter, and Trump’s claim that Ukraine, not Russia, was behind the interference in the 2016 presidential election. She reasoned that Trump would not lie because he had nothing to hide. Klepper reasoned that if Trump were innocent, then he would want everybody to talk. When she concurred, Klepper pointed out that the president had not cooperated with Congress and had made threats over Twitter (now called X) to those who testified against him, in an attempt to intimidate them.
“The woman took a really long beat and she just said, ‘I don’t care.’ That left me speechless, because it was so truthful,” Klepper says. “The reality is she loves Donald Trump. It’s a part of her identity. She believes in this guy, and there’s no piece of information or debate that is going to change that.”
But Klepper doesn’t just roam the streets for interviews. He has also proven he can sit behind the host’s desk. Klepper filled in for The Daily Show host Trevor Noah in October 2016 and then again for a week in April after Noah left the show. During the April stint, Klepper traveled to Kalamazoo to interview Michigan Gov. Gretchen Whitmer over a beer at Bell’s Eccentric Cafe.
“When her folks said, ‘What if we do it in Bell’s?’ I was like, ‘Are you kidding me? I get to fly back to Bell’s and talk to Governor Whitmer about politics for The Daily Show? Like, at my hometown brewery where my son took his first steps? Oh, wow!’” Klepper recalls. “That was a special week in so many ways for me — to host a show that I loved, and for four days I really got to enjoy getting to do this thing that I loved so much. A big part of that was literally coming home and talking about things I care about in a place that is special to me.”
Klepper’s week behind the desk was also an audition of sorts to fill the host spot, which has been vacant since December 2022. But with the show on hiatus due to the writers’ strike, the announcement of Noah’s replacement has yet to be made.
“It’s exhausting and takes a toll on your life, but it is a dream job,” Klepper says. “I’d love to be part of The Daily Show in some way. But wherever it goes, I hope whoever gets that job takes it seriously and has fun because it’s a really lucky seat to sit in.”
If he were given the spot, he says, he’d tell his parents first. “I have to say that partially because my dad’s here right now,” he says with a laugh, nodding to his father, who sits a few seats away.
Nonetheless, Klepper keeps an eye out for new projects. Every month, he hosts “Shit Show,” a monthly live show at The Bell House, in Brooklyn, that mimics a British news panel.
“We invite friends from The Daily Show, writers for all the late-night shows, and other comedians who are in town, and (we) get into the news stories of the week. We riff, we have fun, and we kind of celebrate them in a room with an audience who kind of is also up on the news and wants to talk about stuff,” Klepper explains. “It started as a chance to connect with an audience post-Covid, and now in a time when writers are striking, nobody is making TV. It’s become a chance for late-night writers and all creative types who are out of work in New York City to kind of come onto a stage and have a moment of catharsis.”
Klepper is also working on a narrative show that utilizes his skill set from The Daily Show in a documentary style to portray conversations and interesting storylines that are in the news but a little outside The Daily Show’s content realm.
“It’s been a strange, funny time that, I will say, I didn’t expect — being an improviser and to now suddenly be interacting with very serious people and very silly people all in the same breath,” he says. “It’s an exciting place to be working in.”
Klepper is a New Yorker now, living there with his wife, Laura Grey, who is also a comedian — he met her while performing with The Second City — and their three-year-old son. But that doesn’t mean Klepper doesn’t miss his hometown. When home, he says, he loves going to The Stamped Robin, Bell’s Eccentric Cafe and the Kalamazoo Nature Center and to revisit the K College campus as well as give directions to strangers in true Kalamazoo fashion, based on where businesses used to be.
“My sister (Caycee) and I laugh about how the directions in Kalamazoo are always like, ‘Go up, take a left to where Burdick’s used to be, or take a right where Olde Peninsula was. We’re triangulating everything based on the things as they once were.”
Host with the most?
When Klepper does return, he visits his cousins, sister and parents and works on teaching his young son to not be afraid of birdsong.
“When we came back to Kalamazoo, we found my son is scared of bird sounds. My son is growing up in New York, and birds are scary. But the sirens he’s totally cool with.”
As Klepper’s stardom continues to rise and he rubs elbows with more and more celebrities, he admits he still gets starstruck from time to time.
“On The Daily Show, you would see people all the time. You’re like, ‘Wow, that’s Jerry Seinfeld, that’s Keegan-Michael Key, or that’s Tom Cruise.’ It’s always really fun to see that. But the more time you spend with them, you realize the people you respect most and still hold on those pedestals are folks who work super-hard all the time. And Jon (Stewart) is a great example of someone who became a boss and a mentor and still holds a really high place in my heart because, beyond all of that, he’s just a super-hard worker who put on a really hard show every day.”
Now, as he himself might be an idol on a pedestal for young comedians, Klepper acknowledges both the good and the bad about fame. The good: It’s easier to get dinner reservations and meet nice people wherever you go. The bad: There’s potential for self-centeredness.
But mostly Klepper is grateful for the amount of fame he has. “I benefit from the fact that I’m not that famous and there are many younger, more attractive, famous people than me, so I have a beautiful level of fame. It’s mostly just I get to talk about things I love and get an occasional good reservation here or there.”