Uncut with Jay Cutler: Comedian Dane Cook Talks About His Early Life and the Start of His Stand-Up Comedy Career

by Chris Haney

This week on Uncut with Jay Cutler, we’ve got another funny one for you as comedian Dane Cook joins the show to talk about his life, career, and new stand-up special Above It All that releases on October 5.

The 50-year-old comedian has had a rollercoaster ride of a career over the last couple of decades. It took him 10 years to finally find success with his stand-up career. Yet once he did, Cook blew up and was one of the biggest comedians in the world for a time. That led to movie roles and even a failed TV show, but drama surrounding the comedian derailed his career in the early 2010s.

During his Uncut with Jay Cutler appearance, Dane Cook spoke candidly about some of the drama, which included filing charges against his brother that eventually put him in jail. Cook also opens up about the early years of his career and how he was the first comedian to utilize social media to promote himself and his comedy. He chats about working gigs in the Northeast with fellow comedians Bill Burr and Robert Kelly. Cook also explains his transition from Boston to New York City and then to Los Angeles and how he adapted to each comedy scene.

Dane Cook opens up about his new material and how it came about. He also talks about finally getting back on the stand-up stage once again after years away. He chats further about his new special and shares what’s next as he resets his stand-up career. We’ve got that and a lot more this week with comedian Dane Cook on Uncut with Jay Cutler.

Dane Cook on His Youth and Breaking Out of His Shell Through Stand-Up Comedy

Believe it or not, Dane Cook wasn’t the outgoing, funny guy most people think he would’ve been in grade school when growing up in Arlington, Massachusetts. Cook admitted he had anxiety and was the furthest thing from the class clown when he was a young man. However, when he’d get home, he was much more comfortable around his family and used them as his audience. With an older half-brother and two sisters in the household, he had plenty of family members to test out his comedy on as a teenager.

Yet he finally started to come out of his shell a bit during his junior year of high school. He performed in a few school plays and began working on his stand-up routines he’d been writing since middle school. Following high school, he knew he wanted to give stand-up a real shot. College was a back-up plan at the time. Cook credits his mother and her unwavering support for his early days of getting on stage.

“More than anyone, it was my mom,” Dane Cook shared on Uncut with Jay Cutler. “I think she really wanted to see me overcome the anxiety that I had as a kid. And so telling her I’m gonna go in front of thousands of people and make them laugh when she knew I had problems even walking out the front door for school I was getting worked up and having anxious moments. She was like my first champion. She was also the first person I would bomb in front of as well. So, she’d be like, ‘Honey, that’s… don’t do that.'”

Like almost every other famous comedian, it took years of gigs with no fans before Cook finally got anywhere with his comedy. Repeatedly getting on stage though and facing his anxiety helped Cook move forward not only in comedy but in his personal life as well.

“It’s crazy. You were still getting up on stage in front of random people and trying to make them laugh. Which I think is one of the hardest jobs out there. It’s hard to make people laugh, it’s hard to be authentically funny,” host Jay Cutler said.

“It was tricky,” Dane Cook admitted. “It was definitely like a puzzle that I was interested in continuing to lean into. But to put it simply, even if I had a bad show, a bad set, nothing felt as bad as how I felt just in my regular life thinking, ‘Man, am I an insignificant person?’ But when I go on stage, even if I’m not doing great, there’s something significant about being in that moment. I didn’t want to give up on that.”

Dane Cook Chats About His Early Years As a Stand-Up Comedian

As mentioned, Dane Cook grew up in Arlington, which is only about 30 minutes north of Boston, Massachusetts. Therefore it was only natural that Cook started his budding stand-up career in the Boston comedy scene.

While there in the early 1990s, he rubbed elbows with a couple of up-and-coming comedians you might know, including Robert Kelly and Bill Burr. After Boston, he moved to New York City where he worked with comedian Bill Burr once again. Of course, Burr would go on to become one of the biggest comedians of his generation.

In fact, Burr drove Cook to his first apartment in NYC. Bill was still a dental assistant while they both worked for next to nothing in random comedy clubs at night. Needless to say, the early years of any comedian’s career is far from glamorous.

“Me and Burr were humpin’ around in little s**t box cars from gig to gig,” Dane Cook recalled.

“It’s amazing that small circle of comedians that find each other and have obviously kinda taken over the comedian world the last 20 years. What year was that?” Jay Cutler asked.

“It was fun. It was great. That was like ’94,” Cook answered. “We both started together in Boston right around ’90, ’91. And then there was a good little group of us, man. We were just doin’ stand-up all over the place and trying to figure out how do we win this thing.”

Our host talks to Dane Cook about that and much more on the newest episode of Uncut with Jay Cutler. Make sure to check out his new stand-up special, Above It All, on October 5th releasing on social media platform Moment. You can also watch our entire interview with Dane Cook in the video above, or tune in and listen on Spotify, Apple, or wherever else you listen to your favorite podcasts.