Q&A: Emmy Winner Kyle Dunnigan on Almost Dying on the Freedom Trail

Kyle Dunnigan

Taking a stroll down Boston’s famous Freedom Trail can be a dangerous journey, well, at least according to comedian Kyle Dunnigan.

The Inside Amy Schumer writer and recent Emmy winner, who performs at the Brighton Music Hall this weekend, admits that the historic path nearly got the best of him during a visit to the city as a kid.

“We walked the entire Freedom Trail and I almost died,” Dunnigan says. “It was a lot longer than it looked on a little map.”

Check out what else the comic had to say about his experiences in Boston, how New England has made him “edgeless” as a comedian, and more.

You’re coming to Boston and are no stranger to the area. Tell us about your New England roots?

I went to UConn and grew up in Connecticut. My sister lives in Massachusetts. I grew up in Weston. My mother lives in Westport now, which is basically where I grew up. It’s southern Connecticut.

Have you traveled to Boston a lot over the years?

I love Boston! As a kid, twice I skipped school with a friend to go up to Boston. We walked the entire Freedom Trail and I almost died. It was a lot longer than it looked on a little map. I think I’ve performed in Boston maybe three times. Our podcast was out there about two years ago. I love the Boston crowd.

Did growing up in the New England area have any influence on what you find funny?

I grew up in a very middle class, comfortable environment. A lot of comedian friends of mine had tough upbringings. I really didn’t have that. I’m sure it’s had some influence on what I do. I think a lot of what I do is silly. I like silly humor. I’m like the opposite of a Lenny Bruce or something like that. But to sum up, New England has made me edgeless.

You recently took home an Emmy for that hilarious music video featuring a boy band parody song on Inside Amy Schumer. How’d you come up with it?

Kurt Metzger came up with the concept and I loved the idea. I asked Amy if I could write the music for it because I, as a hobby, write music and it’s usually pretty cheesy. I felt it fit the boy band type of music. All the writers pitched lines, almost every writer got a line in the song, which was cool. It was a very group effort. I just wrote the music and kind of edited it down and made it more musical.

From New Kids on the Block to One Direction, there have been so many boy bands throughout the decades. Which ones had the biggest influence on this song?

I downloaded like four boy band songs. “Bye Bye Bye” by NSYNC, that Backstreet Boys song, “Tell me why”—that one. And then One Direction I really stole their style. It was just more current.

Overall, how would you describe your experience working on the show and with a superstar like Amy?

I’ve been there since the beginning, so it’s been really fun to watch her steadily climb every year. It’s always been the same writers room. It’s very collaborative. Amy is definitely the quarterback and in charge. Jesse Klein is another brilliant head writer. It’s a very nice room. It’s a comforting sort of room. I wish I had more gossip. It’s the greatest job I’ve ever had. It doesn’t feel like a job. A lot of laughing and there’s no competitive edge to the room, which is nice. It’s like one brain.

Kyle Dunnigan performs at the Brighton Music Hall on Saturday, October 10.