The Stern Show welcomed some help this week from talented writer, actor, comedian, impressionist, and Instagram star Kyle Dunnigan. On Wednesday morning, Howard brought him back into the studio for a chat about his life and the state of his career.
“I’m very stressed out,” Kyle joked upon entering the studio. “It’s fun, but it’ll be like, ‘Howard’s talking to about a guy who’s blind—be a guy who gets jizzed in the eye.’”
Considering Kyle’s atypical living situation, the Stern Show gig might not be the only source of stress in his life. He revealed he’s collaborating on a new Hulu series with his ex-girlfriend, superstar and repeat Stern Show guest Amy Schumer. The two are working so closely together he’s recently moved in with her and her husband, chef Chris Fischer.
“I’m living right now with her and her husband,” Kyle said, explaining he’s been at their New York penthouse for a month and a half and even has his own room. He assured Howard the living situation was less awkward than it sounded, thanks in part to the fact his and Amy’s romantic relationship was both brief and quite some time ago.
“The husband doesn’t mind?” Howard wondered.
“We’re bros,” Kyle said, revealing they sometimes play chess together and he often cooks them all delicious food.
“No kidding?” Howard said. “Maybe I’ll stop by because I love to play chess.”
“Eh, it’s kind of packed,” Dunnigan joked.
Schumer isn’t the only talented comedian Kyle has dated over the years. He’s also been in relationships with both Stern Show celebrity superfan Sarah Silverman and Jackie Tohn, who last year gifted Robin Quivers an unforgettable parody of the song “Shallow.”
Howard was impressed by Kyle’s high-profile romances. “May I say you’re almost like a Pete Davidson?” he said, later adding, “You got some résumé. You’re like the Derek Jeter of comedy.”
“Yeah, I date up,” Kyle agreed.
His career résumé is impressive, too. In addition to his stand-up successes and recent credits on shows like “Inside Amy Schumer,” “I Love You, America,” and “Lights Out with David Spade,” he’s also amassed over 600,000 followers on his Instagram account where he regularly posts comedy videos.
“It saved my career. I was dead,” Kyle said, explaining his social media stardom has helped ensure he won't be boxed in as just a TV writer.
His ascension hasn’t been hurdle free, however—he recalled a terrible experience he once had working as a cruise ship comic. “I did one cruise ship and I’ll never do it again,” he told Howard. “I thought, this is gonna be great—a paid vacation—and I was bombing every show.”
“It was mostly wheelchairs and I’m doing this younger material,” he added.
Kyle bombed so hard he even developed a reputation. “I became famous for being bad … and I went to the pool one day and I put on a disguise. I was so humiliated, like I’m O.J. [Simpson],” Kyle said.
He told Howard he managed to make only one friend while onboard, a woman who thought he looked exactly like her recently deceased son. “She wanted to go rock climbing with me and I can’t say no, so now I’m doing activities with her,” Kyle recalled. “And then I could tell, like, I wasn’t acting like her son and I was kind of pissing her off.”
Howard asked Kyle about a rumor regarding another woman he’d apparently rubbed the wrong way, Stern Show regular Whitney Cummings.
“We’re great friends now,” Kyle told him, revealing they’d once had a petty quarrel after she went on a podcast and implied he wasn’t her type. Later, during one of Kyle's visits to the Stern Show, he fired back and said he didn’t want to date Whitney either. Things got more awkward between them when they ran into each other at the gym, but they've since managed to sort everything out.
“She’s a really great person,” Kyle insisted, adding she once even gave him advice on how to dump his girlfriend. “She’s like, you have two lines you say … ‘I’ve decided,’ you put that in there, and then you leave the situation, you say, ‘I’m going to let you process.’”
“Wow,” Howard said. “Is that your plan to keep dating chicks and not actually commit?”
“No,” Kyle responded. “I’d like to get married by the end of this year. No matter who it is … I’ll marry the next person who kisses me.”