Quick answer: Madison, Wisconsin has 8 verified upcoming comedy shows at 3 venues from December 3, 2026 to November 11, 2027. Standouts: Brian Regan and Jordan Jensen at the Barrymore Theatre in December, Rosebud Baker at the Majestic Theatre in January and Eric Andre at the Orpheum Theater in July.
Updated November 11, 2026
Madison comedy shows are lined up from early December all the way to next November, and today the whole country is pausing for Veterans Day. National parks are free to enter today, and plenty of restaurants are thanking veterans with free meals. If someone in your life served, putting a night of laughs on the calendar together is a pretty good thank-you too.
Locally, Madison, Wisconsin is getting into the holiday spirit. Holiday Fantasy in Lights switches on at Olin Park on November 14 and runs through New Year’s Eve, and it is free to drive through after dark. The first Madison Cocktail Festival pops up at Garver Feed Mill on November 14, and Flannel Fest takes over the Barrymore Theatre on November 20.
What’s the mood in Madison right now?
Puffy coats are out, the lakes are getting colder and everybody is pretending they have not started a holiday shopping list. That is the right moment to save one night that is just for you. Nobody has to wear flannel to a comedy show, but nobody is going to stop you either.
The shows below are spread across the Barrymore Theatre on the east side, plus the Orpheum Theater Madison on State Street and the Majestic Theatre on King Street downtown, so you can pick a neighborhood night or a downtown dinner and a show.
What comedy shows are coming up in Madison?
Every date and time below comes from structured ComedyCalendar.com event data, and every link goes to a ComedyCalendar.com event page. Times are Central Time.
| Date | Time | Comedian | Venue | Neighborhood or Area |
|---|---|---|---|---|
| Thu, Dec 3, 2026 | 8:00 PM CST | Brian Regan
|
Barrymore Theatre | East Side, Atwood Avenue |
| Thu, Dec 10, 2026 | 8:00 PM CST | Jordan Jensen
|
Barrymore Theatre | East Side, Atwood Avenue |
| Fri, Jan 29, 2027 | 8:00 PM CST | Michael Kosta
|
Barrymore Theatre | East Side, Atwood Avenue |
| Sat, Jan 30, 2027 | 7:00 PM CST | Rosebud Baker
|
Majestic Theatre | Downtown, King Street |
| Sun, Mar 7, 2027 | 8:00 PM CST | Jeff Arcuri
|
Orpheum Theater Madison | Downtown, State Street |
| Sun, Mar 14, 2027 | 3:00 PM CDT | Bored Teachers
|
Barrymore Theatre | East Side, Atwood Avenue |
| Sat, Jul 10, 2027 | 8:00 PM CDT | Eric Andre
|
Orpheum Theater Madison | Downtown, State Street |
| Thu, Nov 11, 2027 | 7:00 PM CST | Iliza Shlesinger
|
Orpheum Theater Madison | Downtown, State Street |
Brian Regan
Thursday, December 3 at 8:00 PM CST
Barrymore Theatre in Madison
Brian Regan plays the Barrymore Theatre on Atwood Avenue on a Thursday in early December. Big physical bits about the small, everyday stuff that drives everybody a little nuts. An easy pick for taking your parents, your coworkers or a first date.
Jordan Jensen
Thursday, December 10 at 8:00 PM CST
Barrymore Theatre in Madison
Jordan Jensen brings The Wet Hug Tour to the Barrymore one week later, on another Thursday in December. Sharp, honest and quick. Bring the friend who says they are too tired to go out and then has the best time of anyone.
Michael Kosta
Friday, January 29 at 8:00 PM CST
Barrymore Theatre in Madison
Michael Kosta brings Big Dad Energy to the Barrymore on a Friday at the end of January. Dry, confident and happy to poke at whatever everybody is arguing about. A good fix for the long, cold stretch after the holidays.
Rosebud Baker
Saturday, January 30 at 7:00 PM CST
Majestic Theatre in Madison
Rosebud Baker plays the Majestic Theatre on King Street the next night, a Saturday. Dark, smart and fast. Make it a downtown weekend and grab dinner near the Capitol before the show.
Jeff Arcuri
Sunday, March 7 at 8:00 PM CST
Orpheum Theater Madison in Madison
Jeff Arcuri brings The Road Trip Tour to the Orpheum Theater on State Street for the late show on a Sunday in March. Laid-back crowd work and stories that wander off in the best way.
Bored Teachers
Sunday, March 14 at 3:00 PM CDT
Barrymore Theatre in Madison
The Bored Teachers "Is It Friday Yet?!" Comedy Tour takes over the Barrymore on a Sunday afternoon in March. Made for teachers, parents and anyone who has ever survived a group project.
Eric Andre
Saturday, July 10 at 8:00 PM CDT
Orpheum Theater Madison in Madison
Eric Andre brings Subtle to the Orpheum Theater on a Saturday in July. Loud, strange and nothing like a normal summer weekend on State Street.
Iliza Shlesinger
Thursday, November 11 at 7:00 PM CST
Orpheum Theater Madison in Madison
Iliza Shlesinger brings Free Nights & Weekends to the Orpheum Theater on a Thursday in November 2027. It is a year out, which makes it the rare plan you can lock in before you even buy next year’s calendar.
Where to see stand-up in Madison
The Barrymore Theatre at 2090 Atwood Ave. on the east side has four of these shows: Brian Regan on December 3, Jordan Jensen on December 10, Michael Kosta on January 29 and the Bored Teachers tour on March 14.
The Orpheum Theater Madison at 216 State St. downtown has Jeff Arcuri on March 7, Eric Andre on July 10 and Iliza Shlesinger on November 11, 2027.
The Majestic Theatre at 115 King St., a short walk from Capitol Square, has Rosebud Baker on January 30.
Madison comedy FAQ
When is the next comedy show in Madison?
Brian Regan plays the Barrymore Theatre on Thursday, December 3, 2026 at 8:00 PM CST.
Are there comedy shows in Madison in December?
Yes. Brian Regan plays the Barrymore Theatre on December 3 and Jordan Jensen plays the Barrymore Theatre on December 10, both at 8:00 PM CST.
Which big-name comedians are coming to Madison?
Brian Regan, Jordan Jensen, Michael Kosta, Rosebud Baker, Jeff Arcuri, Eric Andre and Iliza Shlesinger all have verified Madison dates between December 2026 and November 2027.
Is there an afternoon comedy show in Madison?
Yes. The Bored Teachers “Is It Friday Yet?!” Comedy Tour plays the Barrymore Theatre on Sunday, March 14, 2027 at 3:00 PM CDT.
Find more Madison comedy
New dates get added all the time, so check the Madison comedy shows page for the full, always-updated list, or browse the Wisconsin comedy shows page for shows around the state. Pick a night and send it to the group chat before the holiday plans fill it up.
