Growing up in Trumbull, Bridgeport-born Robert Dean knew he needed something to separate himself from the crowd and considered several options.
“I needed some sort of identity, so in high school, I decided being a comedian would be the way to go,” he said. “I was never really the class clown but I certainly loved making people laugh. By the time I was 16, I fell in love with comedy as a whole — stand-up specifically, and it became what defined me.”
Dean recently went through his old high school yearbook and his quotes, and laughed about how pretentious he was back then about his craft. Everything he wrote was geared around his being a comedian, but it proved that he was serious about pursuing it as a career even back then.
“Initially, it was all about ‘that looks like fun and I want to do that,’ but the more I learned and opened up, I realized comedy could be pretty much anything as long as it was funny,” he said. “That artistic freedom really excited me and I wanted to get more serious about it.”
After high school, he went to Fairfield University and started doing open mics at the Acoustic Café and other local venues.
“I had never met another comedian because I was performing between usually two acoustic guitarists,” he said. “I decided when I was 22 to move to New York, and that was a shock. All of a sudden, here are all these other people pursuing comedy.”
He slowed down a bit, doing approximately one open mic a week, but he worked hard and eventually was doing his routine almost every night.
“It was hard, but I was on stage and I was happy,” Dean said. “After so many years of wanting to do it and kind of dabbling in it, finally I was pursuing it. From the get-go, I was happy. I was doing the thing I wanted to do.”
It didn’t take long for Dean to develop a strong following, and things have really picked up for him recently. He was named a “Comic to Watch” by Comedy Central, and his new comedy album will be released on April 12. The next day, he’ll headline at the Fairfield Comedy Club.
“It feels good to have this hometown return. I love coming back, and I can talk about my experience growing up here and relate to everyone,” he said. “What doesn’t excite me as much is my entire family coming out. The fact that I get paid to do comedy where there wasn’t really any place to watch it when I was a child is cool. I’m excited there are opportunities now.”
His album “(It’s Not Easy) Being Dean,” on Sure Thing Records, is something he hopes will propel him to the next step of his career.
“I spent the last six years of my life in a windowless basement here in New York working on this,” he said. “These are my jokes from my entire career — my favorite things. It kind of feels like to get this done, it is capturing me at where I am now and I am only going to get better. This is capturing someone who has been going for comedy for 10 years and I want people to enjoy it and I hope they will.”
Reflecting on his decade-plus career, Dean is also excited about being profiled in this paper, and said if his grandmother were alive, she’d be thrilled because she read it every day.
“My grandfather owned a candy store in downtown Bridgeport, so this town is a part of who I am,” Dean said. “I did the Robert Dean Museum last year, which was an incredible experience. Every little step feels like the top and excites me because my career is expanding.”
Dean described his act as being observational comedy, and said if you like his live show, you’ll love the album, and vice versa.
“It’s wacky, but very slice-of-life. It’s personal and biographically but kind of silly,” he said. “I do what I do and I’ve been writing and working for so long now. What this album is and how I perform is just me and what I find funny. That can go from talking about someone who eats Tic Tacs to my own personal paranoia in life.”
When not doing comedy, Dean works in various fields and is currently selling furniture as his “day job.” Although eventually he’s sure the job will find its way into his routine, for now, he tries to keep both jobs separate.
“There’s something about being entertaining and charming that works universally in all jobs, but I usually don’t bring it into my act until after the fact because I need distance,” he said. “There’s something about being direct, and it’s always easier to say, ‘This is what I used to do,’ rather than ‘This is what I’m doing.’”
With the album now completed, Dean is already hard at work on new jokes and new insights and hopes to go out on tour later this year.
“I’m inspired by a combination of things I overhear or notice, and I’ll pull the string and see how far it goes,” he said. “Where I am now will always be a treasure trove of material and observations about life. The more mundane something is to me, the better. It’s fun for me to point out things that people don’t notice. My job is to obsess about things and spend my time writing it and working on it until the whole world sees it and laughs at it.”