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How Comedian Ken Garr Traded It All For Stand Up


Comedian Ken Garr has finally seen his grind from both the Chicago and LA comedy scenes pay off with his first big special American Hero recently hitting Amazon
Prime and YouTube. Although every comic takes a big risk pursuing stand up, Garr gave up a life many wouldn’t have to chase his dream of being a full-time comic.

Ken was making good use of his finance degree from the University of Iowa. In his mid-30s, he found himself working as a managing director in sales with a major stock exchange’s Chicago office, pulling in a salary close to $200,000.

“It was like the dream job. I was meeting with the CEO and CFO of Fortune 500 companies. I would call the secretary of the CEO, and they would patch me through right away,” Garr, who recently returned from playing the Middle East and becoming the first american comedian to perform publicly in Saudi Arabia in 3 years, told me of his previous gig.

“I was keeping them [up to speed] on things that were happening in the market and things that were going on with their stock. I helped them to essentially draw investors to their companies, help them create a plan to do so. So it was a pretty high level job.”

“I loved my customers.” Garr added.

Then, in 2013, nine months after starting his “dream job” in finance, Ken had an epiphany and realized it wasn’t the career or life he wanted.

“I remember that I was sitting in the room with the CEO of Buffalo Wild Wings up in Minneapolis, and I just couldn’t stop thinking about doing an open mic that night.

“And I couldn’t stop thinking about— the fact that it was February, it was three degrees in Minneapolis, and I knew at that moment that I just wanted to do stand up full-time, and that I had this dream job that anybody in finance would kill for, and I just wanted to go do stand up. And so I put together a plan.”

After 13 years and a few jobs in finance, Ken decided he was going to quit his current role on August 1 of 2013 and pursue stand up full-time.

In a twist of fate fitting for a comic, his employment was terminated on July 31 after falling one sales contract short of his quota after his relationship with his supervisor had been deteriorating and the two weren’t seeing eye to eye as comedy’s call grew louder and louder for Garr. Regardless, it was time to make a run at his dream.

Ken already had nearly a decade of comedy experience under his belt before fully immersing himself in the new career. He had completed Second City Chicago’s conservatory program, was doing open mics all over the Chicago area, and was working paid gigs at small clubs.

Ahead of 2013, Garr was married, had a house and had a full-time job outside of comedy. He didn’t see that changing back then.

Ken and his then wife split up a year before he left finance for comedy.

“I remember sitting across at dinner from my first wife and saying, ‘Oh, I would never do stand up full-time. It’s not the life that I want to live. I want to have money. I want to have security. I want to have health insurance. I want all these things that you’re supposed to have in life,’” Garr recalled.

“And the thing is, the more I ended up doing it, and the better I got at it, I mean, the more I just loved it. And it’s not that she hated it. She was very supportive. But at the same time, it just felt like she wanted more of kind of a nine-to-five guy and more stability.

“And so we ended up splitting up. And I don’t know if I would say comedy was the number one reason for it, because I still had a full-time job when we split up.

“But I think it was that I wanted to spend every weekend and every vacation day doing stand up, and I think she wanted to have kind of a more normal life. And I never faulted her for that. … So I think ultimately we got divorced because we just wanted two very different lifestyles.”

The divorce wasn’t as tough as it was for most couples ending their marriage, according to Ken.

“We just moved on with our lives. And she’s happy and has a great life as well,” Garr said.

Before moving to LA, Ken got a taste of Tinsel Town in Chicago, working with national headliners that came to the local clubs. One day, he got a call from the Chicago Improv (located in Schaumburg, Illinois), asking if he’d open for comic and actor Brad Garrett (Everybody Loves Raymond, ‘Til Death, Fargo TV series) who’d end up having a major impact on Garr.

The two got along, talking poker before the first show at the club.

“And I remember the first show he did, he had an okay set. He does a lot of crowd work, and if the crowd’s not into it, then you can only get so much out of them. And so he came in and he sat down, and I sat down next to him and I go, ‘So when did you lose them?’ Ken recalled with a laugh. “He goes, ‘About two minutes in, Kenny.’ And from that point, we were really just kind of hit it off.

“And he was so nice to my family. They came in and then took pictures, and he took pictures with everybody, and was just so humble and so nice. And at the end of the weekend, I gave him a thank you note.

“I don’t know if I’d ever done this before, but I just said, ‘Thank you for being so nice with my family. And if you ever need an opener in the Midwest, I would love to work with you again. You’re a genuinely great person.’

“And then six weeks later, I got a call from his booker and said, ‘Yeah, Brad Garrett wanted me to book you for his room in the Tropicana in Las Vegas.’ And I was like, ‘What?’ I mean, I didn’t even know he had a room. I had no idea. So I went out there, I did the week. I mean, up to that point, it was the coolest thing I’d ever done. Your name on a billboard.”

Ken went on to play Garrett’s room at the Tropicana and his current one at the MGM Grand countless times. Brad later set Ken up with his acting coach.

In the late summer of 2013, Ken arrived in LA, ready to implement his plan no matter what it took.

“I moved to California with the clothes on my back and $60,000 in the bank. So for me, it was like, ‘You can try anything for a year.’ And I knew that I didn’t want to be in corporate America,” Garr said. … “I really wanted to give this a try. And so, yeah, I saved up a bunch of money and I traded in my Lexus SUV for a Honda Civic, all the managers at the dealership came in, they’re like, ‘We got to ask you, what are you doing?’

“I minimized my life. I sold my house in Tinley Park (southwestern suburb of Chicago). I got rid of essentially everything that I owned, and I moved into a small, tiny one bedroom apartment in Burbank, California, paying almost the same as what I paid for my mortgage.”

Ken was cast in an Ed Asner movie within the first week of the move, but soon learned how scarce big projects can be to Hollywood newcomers.

Although he was working steadily as a comic on LA stages and on the road, passing at the prestigious Hollywood Improv, Ken began driving an Uber
around 2016, which fit his schedule around auditions and stand up shows, so he could earn enough money to stay in California.

“So I started Ubering, and it’s kind of funny because I would— I try not to be that Uber guy that talks to people, you know what I mean? I just kind of kept quiet, but every once in a while, they’d strike up a conversation,” recalled Garr. “And I remember this one time I picked up a financial advisor, and I was like, ‘Oh, how are the markets?’

“He’s like, ‘Oh, they’re pretty good.’ … I go, ‘But keep an eye on the price of concrete in China.’ I’m like, ‘If that goes down, that means they’re in a recession. We’re going to be in one too.’ And he was like, ‘Who are you?’ But I knew the language.”

Ken picked up more notable show business work and mingled with more top level stand ups as a few years went by and quit driving for Uber right before the pandemic began.

He was the head writer for former first lady Michelle Obama’s “Why We Vote” telethon, which was filmed at YouTube Studios and carried by Comedy Central and Ellen Degeneres’ production company. It was broadcasted to millions of people and gave him the opportunity to work closely with A-list stars, writing for actors like Charlize Theron and Natalie Portman.

At LA clubs like the Hollywood Improv, Garr has shared the stage with such comedy legends as Adam Sandler and David Spade.

Ken met his current wife, Jennifer, the night he got divorced when he performed in a show at Riddles Comedy Club in Alsip, Illinois. He learned dating right after a divorce could be tricky. Garr and “Jen” dated for only a month after meeting but formed a close friendship that lasted six years.

She later married another person and got divorced.

“And when she got divorced, I think we both realized that we were supposed to be together and we were meant to be together,” Ken said. “I literally met her the day I got divorced, and six years later, we started dating [seriously]. And eight years later, we got married. And we’ve been married for two years now.”

Garr’s comic lifestyle works for Jennifer, who only ever knew Ken as a comedian.

“I think she loves the enthusiasm and the passion that I have toward it, and I bring it into other areas of my life, including our marriage,” Garr said.

Ken has a much different perspective on life now after seeing his gamble on comedy, LA, and himself payoff.

“I think my biggest accomplishment here in Los Angeles was having a belief in myself that I can actually do this. And really, kind of, it’s funny because you kind of redefine what success means,” he stated.

“So for me, when I moved here, I was like, ‘I want to be on The Tonight Show. I want to be on Letterman. I want to do this….” And now, having been here for a while, it’s like, ‘I want to pay my bills, and I want to have a happy wife,’ you know what I mean?

“So all these accolades that I think that are important for people, they became less important for me, and what became most important for me was the work, that I can say that we had the highest voter turnout in history, and I played a little bit of a part in that.”

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