This weekend, wildly popular comedian Tom Segura will drop by Milwaukee for a trio of Riverside Theater shows that will be split between Friday, November 14 and Saturday, November 15. All three shows are sold out. If you didn’t manage to score tickets in time, you’re in luck. These performances, which are part of Segura’s ongoing “Come Together Tour,” are going to be recorded and released as an upcoming comedy special.
While that’s a big deal in itself (and a testament to Milwaukee’s gorgeous venues and the caliber of its comedy audiences as a whole), it’s far from the first time our fair city has served as the backdrop for a stand up special. Over the last 15-plus years, more than a dozen comics have decided to immortalize material on film while standing on a stage in Milwaukee. From local favorites playing for hometown crowds to worldwide stand up sensations bringing cameras with them to the Cream City, here are 13 comedy specials that were shot in Milwaukee.
Charlie Berens — Midwest Goodbye (2024)
While Charlie Berens’ foray into Badger State-specific comedy was “The Manitowoc Minute,” he looked Milwaukee’s way when it came time to record his 2024 special entitled Midwest Goodbye. (He totally missed an opportunity to call it “The Milwaukee 58:06” instead.) The special was recorded in March of last year during a weekend of Riverside Theater performances that were part of the affable actor/stand up’s “Good Old Fashioned Tour.” Berens has another special due out soon, which was recorded at the Appleton Performing Arts Center. To quote Mr. Berens himself, let’s “keep ‘er movin'” to the other Milwaukee-shot specials on this list.
Louis CK — Hilarious (2010)
Actually, let’s just acknowledge this happened and move right along to the next entry, shall we?
Jeff Dunham — Jeff Dunham’s Very Christmas Special (2008)
About a decade ago, wisecracking puppeteer Jeff Dunham was at the height of his popularity and regularly packing arenas the world over with people eager to hear borderline racist jokes delivered by dummies who doubled as broad stereotypes. As the ventriloquist neared his peak, he came to the Pabst Theater in the summer of 2008 where he shot Jeff Dunham’s Very Christmas Special before a crowd decked out in winter jackets and holiday sweaters. Despite featuring poorly-aged—eh, they were actually pretty offensive regardless of when they came out—songs by “José Jalapeño” and “Achmed The Dead Terrorist,” the Milwaukee-made Comedy Central holiday spectacle attracted 6.6 million viewers, which was the network’s highest rated special at the time.
Kathy Griffin — 50 And Not Pregnant (2011)
For a self-proclaimed D-list celebrity, Kathy Griffin has amassed quite the career. Between 2009 and 2013, the actress and comedian released an astounding 12 specials, most of which were “live” (“with enough delay to work in the steady wave of bleeps”) telecasts on the Bravo network. In 2011, Griffin decked out Riverside Theater’s stage for the filming of 50 And Not Pregnant, the acerbic and polarizing comedian’s 13th special. The 45-minute set found her brazenly tackling topics like Whitney Houston, Sarah Palin, Justin Bieber, and hate mail. It was later released as her fourth comedy album.
AJ Grill — I’ll Quit When I’m 30 (2023)
In late 2022, on the cusp of his 10th year performing stand up, Milwaukee (by way of Iowa) comic AJ Grill said farewell to old material and set out to start fresh in 2023. Before doing so, Grill gathered an audience and some cameras at Hear Here Presents in the Lincoln Warehouse and recorded two sets to be released as a special. I’ll Quit When I’m 30 came out in 2023. Thankfully, Grill did not quit and is still among the most active and all-around best comedians working in Milwaukee right now.
Anthony Jeselnik — Bones And All (2024)
Respected roaster, master of dark humor, and The Jeselnik Offensive namesake Anthony Jeselnik has released a total of five comedy specials over the course of his nearly quarter-century comedy career. The most recent among them, Bones And All, was filmed at Pabst Theater in April 2024 and released on Netflix later that same year. Milwaukee even makes it into some of the special’s material.
Kathleen Madigan — Bothering Jesus (2016) AND The Family Thread (2025)
Midwest native Kathleen Madigan is no stranger to Milwaukee. Beyond routinely visiting the city over the course of her 30-plus-year comedy career, the veteran humorist has now shot two specials at Milwaukee’s historic Pabst Theater. The first is the tremendous Bothering Jesus, which came out in 2016. The second one, The Family Thread, was filmed in town this past April and will be released on Amazon next week.
Ralphie May — Too Big To Ignore (2012)
Though Ralphie May tragically passed away in 2017, the comedian and runner-up on Last Comic Standing‘s first season left behind an extensive and impressive body of work in the form of albums and specials. One such special, 2012’s Too Big To Ignore, found the comedian at the peak of his popularity (and arguably at his funniest) before a Milwaukee crowd and a cluster of cameras at the Pabst Theater.
Damon Millard — Nothing To Nobody (2024)
Though he’s a New York native (and lives back on the East Coast now), Damon Millard cut his teeth in the Milwaukee comedy scene as a member of the Caste Of Killers comedy collective. Fittingly, when the time came to record his debut special, Millard returned to the area to set up a trailer park facade inside The Laughing Tap and shoot Nothing To Nobody in late 2023. The special was released by Comedy Dynamics in 2024 and is available to stream on most platforms.
Colin Mochrie and Brad Sherwood — Two Man Group (2011)
Whose Line Is It Anyway? regulars and improv juggernauts Colin Mochrie and Brad Sherwood have an incredibly unique relationship with Milwaukee. The dynamic duo—who can pretty much be counted upon for at least one Milwaukee performance every year—has performed more than 20 shows in the city. Given the special connection Mochrie and Sherwood have with Milwaukee, it’s only fitting they chose Pabst Theater as the filming site of their 2011 TV movie Colin & Brad: Two Man Group, which was shot in 2010.
Spinal Tap — Unwigged & Unplugged: An Evening with Christopher Guest, Michael McKean and Harry Shearer (2009)
In accordance with the 25th anniversary of This Is Spinal Tap, a comedy classic and pioneer of the “mockumentary” film genre (which actually was the basis for the Shank Hall name), famed director Christopher Guest and his co-stars/fictitious bandmates Michael McKean and Harry Shearer came to Milwaukee’s Riverside Theater in 2009 to play unplugged (and unwigged) renditions of Spinal Tap songs, along with a few cuts from A Mighty Wind, with a great deal of between-song banter thrown in for good measure. On a scale of 1 to 10, we give the special an 11.
Chastity Washington — Live At Dandy (2023)
Talk to virtually any Milwaukee comedian long enough and the name Chastity Washington will eventually come up. With more than 30 years of comedy experience, a respected one woman show, a steady gig opening for Charlie Berens, as well as the love and admiration of an entire comedy scene behind her, Washington is nothing short of a local legend. In 2023, that legend extended beyond city limits with the release of Washington’s Live At Dandy comedy special. As the name suggests, it was recorded at Dandy—an events space on Milwaukee’s west side—and it’s just plain great. Watch this special and see Chastity live whenever you can.