Emily Winter may have just moved back to Madison last fall, but she wears her love for the community literally on her sleeve. On her left forearm is a tattoo of a red cardinal, a homage to her time as editor-in-chief of the Daily Cardinal at UW-Madison.
Winter left Madison for an internship on Comedy Central’s “The Colbert Report,” and embarked on a career in comedy that included writing for The New Yorker and The New York Times and performing standup shows around the country.
When she and her husband, fellow comedian Chris Calogero, moved to Madison in October, they began looking for a place to host a monthly comedy/variety show. They found it in an unlikely place — a train car. “TrainCar Comedy” is held in a stationary railcar/event space called the Local Motive, located on the rails next to The Harvey House off E. Washington Avenue.
Last month’s inaugural show sold out, and the upcoming show on Feb. 26 will feature sets from both Winter and Calogero, as well as Milwaukee comedians Dana Erhmann and Simba Soto, Madison comedian Charlie Kojis, and Madison musician Nell Blevins.
Over coffee at the Colectivo on Williamson Street, the couple talked about the pros and cons of doing comedy in a train car, how to design the perfect comedy show, and their favorite places to eat and drink in town:
How are you finding the comedy scene in Madison?
Winter: I've been really excited just with our little train show. I promote these giant traveling shows, and when we found the train, it was like a perfect small place to try out some new jokes. Like if I’m writing something I want to submit to The New Yorker, let’s try it out and see how the audience reacts, and I can record it and listen so I can make it better. One thing about Madison is that people are smart.
Calogero: People are really nice and open to recommending you for things, and people are throwing their own shows. Madison has this big town/small town feel, which is very cool. Everybody’s been very welcoming. There’s no ego about it.
Why did you decide to start the monthly train car shows?
Calogero: Emily is always very on top of wanting to throw a show when we're in a new place, because it does give you some cachet in the scene. For us personally, it allows us to control a modicum of stage time, and if we aspire to have repeat customers, it forces us to write new jokes. It’s a good give-and-take for us and for the comedians. We’re introducing you to comedians, maybe some different variety acts. So it just works out for everybody.
Winter: I was just scouring venues online, and I came across this place, and the owner was super receptive to the idea. It’s so cute and classy, and the cocktails are way too cheap. They have the best martini I’ve ever had.
What’s it like to do comedy in a train car?
Winter: It's both good and challenging. Comedy loves low ceilings, getting people squished together, nice and tight, when there's not too many distractions. So in that regard, it's the perfect comedy space. But then again, it is a tube, so you kind of want there to be like more people sitting across. But it is dark, and so hopefully people feel comfortable to laugh and enjoy themselves and not feel self-conscious.
Comedians Chris Calogero and Sasha Rosser perform at the first TrainCar Comedy show in January. (Photo by Emily Winter)
How do you build a successful comedy show?
Winter: I love producing live comedy. I had a podcast miniseries called “How To Produce Live Comedy” from 2018 that I still get young kids writing me about. I think there are a few things. One is that the perfect length of a comedy show is 75 minutes. If you go over 90, you’re going into really treacherous territory. And if you go 45 minutes, people are like, “Oh, it’s over?”
Having a variety of voices is good, and one thing I like to see is a variety of ages and experience levels. Sometimes you can give a new person a chance if you see their potential.
Where do you like to eat in Madison?
Winter: I could live and die at the Crystal Corner. We've been walking our dog now into Green Room, and going to Ideal, Mickey’s Tavern for brunch. We get Ha Long Bay all the time.
So basically you just go up and down Willy Street.
Winter: I’ve almost bought the Ace Hardware “We’ve been 100 Years on Willy Street” T-shirt like three times.
