Mason Williams
A man wearing referee's shirt and a green trucker cap and a woman are on a stage each with their own microphone.
Chris Calogero, left, and Emily Winter have many comedic irons in the fire.
2026 is going to be a busy, busy year for Chris Calogero and Emily Winter, Madison-based multi-genre creatives.
Between producing and hosting local shows; touring with live comedy shows on the East Coast; writing a Wisconsin-based novel; creating an independent short film; and writing and recording stand-up albums, this power couple can’t stop entertaining the masses — regardless of the medium. Isthmus chatted with the duo over Zoom to discuss comedy writing, live shows, and short filmmaking.
After getting her journalism degree at UW-Madison, Winter, 41, born in Illinois, went on to write, perform and produce comedy in both New York City and Los Angeles. Calogero, 43, was born in New Jersey and has been doing stand-up for 18 years, going back and forth between New York City, Los Angeles — and now both of them are in Madison as of October 2025. The pair met in the Big Apple and married in 2019. Now, they’re tackling multiple creative endeavors simultaneously.
Winter knew she wanted to use Madison’s train-car bar, Local Motive, as a stage space and as an area to foster creative, off-the-wall shows with local talent. “I went to look at it…and I was so charmed by it,” she says. “The owners put so much love and care into making it very classy, but very fun,” she says, “like a place where you can get drunk, so you don't feel like it's not so classy that you're afraid to get drunk.” Thus TrainCar Comedy, a monthly comedic variety show, was born. Winter loves that the train car “is a place that feels like a creative haven…so that we can focus on what we're doing, rather than filling it up.”
TrainCar Comedy allows for wackier approaches than less intimate venues. In one show, Winter used the audience as a litmus test for jokes she was writing for a different comedian. “I explained [the concept] to the audience, and I let them decide which ones they liked the best, and they were very honest with their feedback,” she says, laughing. TrainCar Comedy allows them to “be a little bit experimental.”
The two both perform and host. This week Winter hosts, alongside Madison comedians Lizzie Kirch and Chuky Razo, and Calogero will perform.
Calogero says Local Motive’s owners and managers have been very supportive: “That's been really a boon to have the venue and the people running it on your side.”
For Calogero, his film, Gimme a Call, is on the front burner for 2026. The script reflects his self described status as a “big old movie nerd.”
“I have a lot of ideas about what I want from movies and what kind of movie that I aspire to be in,” he says. As an actor, he’s interested in “having a character that's not you, that can say jokes that maybe wouldn't work for you on stage.”
His Gimme a Call (logline: “A loveable but absent-minded criminal realizes he’s made one too many mistakes and must face the dire consequences. But not before a final call home”) is on the front burner for 2026. With a director picked, an excited agent, and the initial stage of financing secured, Calogero is ready to put PDF to MP4.
Winter is continuing to work on her novel, Dear Albert. It’s “about a high school nerd with a debilitating stutter who writes a funny advice column for his student newspaper under a pseudonym, and everyone loves it,” she says. It takes place in 2010, which is when she started writing it as a regular series for her former job as editorial director of SparkNotes and its teen blog; she retained the rights when she left the company.
“I hope [Gimme a Call] gets picked up and for zillions of dollars so we can buy a tiny little house on Jenifer Street,” says Winter.
The next TrainCar Comedy takes place at Local Motive on March 26. Winter has teamed with local artisan cheesemonger Fromagination to present “something weird” at the beginning of the show: a cheese Expert! Audience members will try the cheeses while learning about the cultural significance of Wisconsin’s golden product.
Winter will also be hosting a fundraiser for The Badger Project, an independent news nonprofit, at Roxxy on May 7. This spring, Winter’s taking her other show, One Liner Madness, on tour along the East Coast. On May 9, Winter plans on doing an “adult show-and-tell” at Aubergine, on Willy Street. She also teased hosting a “a female Elvis impersonator” at a future show, Austin Butler be damned.
Ultimately, Winter and Calogero want to make something lasting in Madison. “Build the show,” says Calogero. “Get the word of mouth out. Make it a scene. Make people understand that when they come here, they're going to see good comedy. …And we are on board for however long that takes.”
