It’s sad, but it’s true: another summer is coming to an end. Though we’re entering the final weekend of the season, it’s not all bad news. For example, Milwaukee and its surrounding cities are still hosting a ton of festivals this fall (more on that next week!). While those events are already sure to make this autumn an enjoyable one, there are also a ton of musicians, comedians, and other entertainers coming to traditional venues this fall. And that’s not even counting recurring Milwaukee Record events like our Halftime Show series, Avalon film screenings, and Midweek Music concerts. There’s a wealth of great shows coming to the greater Milwaukee area in the next three months. Here are 27 standouts from the bunch.
Thursday, September 26 and Friday, September 27
Jackie Kashian @ Milwaukee Improv
Since leaving her hometown of South Milwaukee, Jackie Kashian has sustained a long and successful career in comedy that includes a Comedy Central special, a few Conan appearances, and her long-running Dork Forest podcast. She’ll return to the region for a total of three performances over two nights.
Friday, September 27
Alkaline Trio + Spanish Love Songs, Slomosa @ The Rave / Eagles Club
A few months removed from putting out its tenth album, Blood, Hair, And Eyeballs, Alkaline Trio will take the stage at The Rave in belated support of the return-to-form record. Spanish Love Songs and Slomosa open.
Monday, September 30
The Roast Of Milwaukee @ The Cooperage
Milwaukee Record’s long-running “Roast Of Milwaukee” event is back! Like previous years, the event—which is done in association with the Milwaukee Comedy Festival—will feature a stacked cast of local comedians gently (or, in some cases, viciously) making fun of our fair city. This year’s event features a wide range of locally-sourced Roasters including Dana Ehrmann, AJ Grill, Luise Noé, Ryan Mason, Tim Higgins, Syed Hasnain, Elijah Holbrook, Kay Baratti, as well as a few extra special surprise guests dropping in to take some swipes at the city. And the laughs won’t just be at the expense of Milwaukee. A portion of the show’s proceeds will be donated to Milwaukee Women’s Center.
Friday, October 4 through Sunday, October 6
Pete Holmes @ Milwaukee Improv
Pete Holmes has enjoyed quite the career. Through the years, he’s starred in a loosely biographical HBO series called Crashing and a CBS sitcom called That’s How We Roll, hosted a late night TBS talk show bearing his name, voiced “The E*Trade Baby,” recorded hundreds of episodes of his popular You Made It Weird podcast, wrote a book Comedy Sex God, and guest wrote some episodes of The Simpsons. However, Holmes is a standup comedian first and foremost. Following last year’s one-nighter at Turner Hall, the multi-talented comic—who started out in Chicago and was no stranger to Milwaukee mics—will return to the Midwest to treat Milwaukee Improv in nearby Brookfield to five shows spread over three October nights.
Saturday, October 5
Mike Viola + L.A. Exes @ Shank Hall
The name Mike Viola may not immediately jump off the screen, but for anyone who’s paid attention to the last couple of decades of rock and pop music, it’s likely they have come into contact with his work. The voice on that infectious titular tune from the film That Thing You Do? That’s him. The songs in the John C. Reilly vehicle, Walk Hard: The Dewey Cox Story? Viola was one of the primary songwriters. Panic! At The Disco and Mandy Moore producer credits? They’re on his resume as well. This is just a minuscule sampling of the pies Viola’s hands have been in. Almost exactly a year removed from playing Cactus Club, the accomplished will return to Milwaukee to perform at Shank Hall. L.A. Exes open.
Sunday, October 6
Mean Jeans + Watermelon, Chinese Telephones @ X-Ray Arcade
Long-tenured punk trio Mean Jeans are coming to Cudahy to play a show in belated support of Blasted, which the band released on Fat Wreck Chords in February 2024. Watermelon and Milwaukee’s own Chinese Telephones open.
Tuesday, October 8
The Get Up Kids + Smoking Popes @ The Rave / Eagles Club
Wanna feel old? The Get Up Kids released Something To Write Home About 25 years ago. That’s a quarter-century! Damn. In honor of the occasion, the seminal Kansas City emo project will come to The Rave to play songs from that celebrated album. Oh, and they’re bringing veteran Chicago pop-punkers Smoking Popes along with them.
Thursday, October 10
Advance Base + Apollo Vermouth, Katie Malco @ Lilliput Records
Using the “Advance Base” moniker, Chicago musician Owen Ashworth crafts lo-fi story-driven output that manages to range from humorous and off-kilter to devastatingly beautiful. Some 10 months after playing Cactus Club, the multi-instrumentalist will come back to Milwaukee to headline an all-ages affair at Lilliput Records that also features Apollo Vermouth and Katie Malco. The show begins at 7 p.m.
Friday, October 11
Horseshoes & Hand Grenades + Ladybird @ Pabst Theater
Instead of its usual New Year’s Eve appearance in Milwaukee, Horseshoes & Hand Grenades will play Pabst Theater a few months earlier this year. Preceding the central Wisconsin roots music mainstays is Milwaukee’s own Ladybird, who will cap off an extremely accomplished year with its biggest show yet.
Friday, October 11 through Sunday, October 13
Bill Bellamy @ Milwaukee Improv
Actor, longtime MTV VJ, alleged creator of the term “booty call,” and veteran comedian Bill Bellamy will drop by the Milwaukee Improv in nearby Brookfield to treat the suburban club to a total of five performances spread across three nights.
Saturday, October 12
Hotline TNT + Disq, Cry Baby @ Cactus Club
Brooklyn’s Hotline TNT will bring its psych-tinged shoegaze to the cozy confines of Cactus Club for an October 12 show that has the potential to be an intimate show you’ll brag about being at a few years from now. Disq and Cry Baby will open things up.
Saturday, October 19
Lil Wayne + Saweetie, Selfish Sons @ Fiserv Forum
A Lil Wayne show in Milwaukee may not be rare (like Mr. Clean with hair), but we’re still pleased to report that the veteran rapper (and Green Bay Packers superfan) is scheduled to play Milwaukee’s Fiserv Forum on Saturday, October 19. Saweetie and Selfish Sons will play in support.
Thursday, October 24
Stevie Wonder @ Fiserv Forum
What needs to be said about Stevie Wonder? Over the course of his 60-year music career, he’s written and performed some of the planet’s most beloved and iconic songs that will live on forever. You’ll have a chance to see the 74-year-old legend in Milwaukee when he comes to Fiserv Forum on October 24 as part of his “Sing Your Song! As We Fix Our Nation’s Broken Heart” tour.
Friday, October 25
Ms. Pat @ Pabst Theater
The life story of Patricia Williams (aka Ms. Pat) is nothing short of astounding. Once a teen mom who was selling drugs in Atlanta, she turned her life around and, by way of her incomparable perspective and undeniable talent, shifted her focus to comedy. In the years that followed that significant life change, Ms. Pat has amassed an abundance of TV credits, started a popular podcast, wrote a critically-acclaimed and NAACP Award-nominated memoir, and has toured extensively. Ms. Pat will drop by Pabst Theater on October 25 for a night of boundary-pushing comedy.
Monday, October 28
M.A.G.S. + Barely Civil @ Cactus Club
Fresh off playing the Milwaukee Record Stage at Bay View Bash, M.A.G.S. and Barely Civil will head a few blocks east to bring their early-autumn tour to a close at Cactus Club. Don’t miss it!
Saturday, November 2
The Menzingers @ The Rave / Eagles Club
The Menzingers don’t come around Milwaukee all that often, so when they do, it’s to be cherished. A year after releasing the band’s latest, Some Of It Was True, the pride of Philly (by way of Scranton) will come to The Rave.
Wednesday, November 13
Big D And The Kids Table + We Are The Union, Devon Kay & The Solutions @ X-Ray Arcade
Over the course of the band’s 30-year run, Big D And The Kids Table has released 11 studio albums, traveled the globe, and earned a place as one of the planet’s premier ska-punk projects. The Boston band will come to Cudahy to head up a show at the “Very Famous” X-Ray Arcade that also includes We Are The Union and Devon Kay & The Solutions.
Modest Mouse + The Black Heart Procession @ Riverside Theater
Wanna feel old? Modest Mouse released Good News For People Who Love Bad News 20 years ago. That’s two decades! Damn. In honor of the occasion, the seminal Washington indie rockers will come to Riverside Theater to play songs from that celebrated album. Oh, and they’re bringing The Black Heart Procession along with them.
Thursday, November 14
Wild Pink + John Francis Flynn @ X-Ray Arcade
New York indie rock stalwarts (and semi-regular Milwaukee visitors) Wild Pink will make its Cudahy debut with a X-Ray Arcade show that also features John Francis Flynn.
Thursday, November 14 through Saturday, November 16
Dana Gould @ The Laughing Tap
Between his decades of stand-up experience, his oodles of TV appearances, and his years as a writer and producer on The Simpsons and Parks And Recreation, we think it’s safe to call Dana Gould a legend. The “comic’s comic” will bring his incomparable perspective and thousands of hours of on-stage experience to The Laughing Tap for a total of five performances spread over a three-night run.
Friday, November 15
Telethon + Breakup Tour, Nick Wilkinson And The Featured Players @ Cactus Club
Wanna feel old? Telethon released Hard Pop five years ago. That’s half a decade! Damn. In honor of the occasion, the Milwaukee-born project will come to Cactus Club to play songs from that celebrated album. Oh, and they’re bringing Breakup Tour and Nick Wilkinson And The Featured Players along with them.
Friday, November 15 and Saturday, November 16
Sam Jay @ Milwaukee Improv
Sam Jay, is an accomplished comic who you might also know from her work as a Saturday Night Live staff writer and an actor on TV shows like Bust Down and films like You People. About a year removed from the release of her HBO special, Sam Jay: Salute Me Or Shoot Me, Jay will drop by Milwaukee Improv in nearby Brookfield for a pair of shows spread over a two-night span.
Friday, November 22
SistaStrings @ South Milwaukee Performing Arts Center
SistaStrings, which consists of classically-trained siblings Monique and Chauntee Ross, has been a fixture in Milwaukee music for the better part of the past decade—both with their own output and by accompanying other area artists. Now based in Nashville, the Ross sisters have quickly found their careers reaching unimaginable heights of late. In recent years, they’ve played arenas and massive music festivals all over North America while supporting world-renowned talents like Allison Russell, Jason Isbell, and Brandi Carlile. Along the way, they’ve performed at the Grammys, played late night shows, sat on stage during Joni Mitchell’s recent live return, and recorded a dual album with Peter Mulvey that was released on Ani DiFranco’s label. SistaStrings will return home a few days before Thanksgiving to take center stage at the South Milwaukee PAC.
Saturday, November 23
Ryan Necci And The Buffalo Gospel + Joseph Huber, Maximiano @ Vivarium
Even though Ryan Necci—the founding member, bandleader, and namesake of Ryan Necci And The Buffalo Gospel—now calls Tennessee home, the Milwaukee expat and professional songwriter returns to his home region every November and brings the band out for a Turkey Day-adjacent concert. This year, Necci and company will makes its Vivarium debut the Saturday before Thanksgiving. Joseph Huber and Maximiano add local support and make this a certified can’t-miss show.
Maria Bamford @ Turner Hall
Minnesota-raised comic Maria Bamford has been either crushing or absolutely alienating comedy audiences (at about a 50/50 ratio) since the late 1980s. About as “alternative” as alt-comedy gets, Bamford—by way of her inimitable comedic style that’s as off-kilter as it is uproariously funny—has gone on to do ample voiceover work, star in Lady Dynamite on Netflix, and film a few wholly unique comedy specials. You may also recognize her from her unsettling Target commercials. Knowing nothing about her recent material, it’s safe to say you’ll never see anything like her forthcoming Turner Hall appearance again.
Friday, November 29 through Sunday, December 1
Pete Lee @ Milwaukee Improv
After growing up in Janesville, Wisconsin, Pete Lee has gone on to perform on Letterman, guest on The Tonight Show (FIVE TIMES and counting!), and rack up a wide variety of credits that include notable TV shows like Last Comic Standing, As The World Turns, Best Week Ever, Comedy Central’s Roast Battle, and much more. He’s released comedy albums, put out a Comedy Central half-hour special, and has performed more than 500 shows at colleges around the country. Lee will return to the region November 29 through December 1 for a total of five Thanksgiving weekend shows at Milwaukee Improv.
Saturday, December 7
A Nostalgic Night With Macaulay Culkin @ Miller High Life Theatre
What could be better than watching Home Alone a few weeks before Christmas? How about watching Home Alone and then getting to witness a moderated interview and audience Q&A with the incomparable Macaulay Culkin himself! Well, you’re in luck because Mac will be in the house for an unforgettable evening that’s being called “A Nostalgic Night With Macaulay Culkin Following A Screening Of Home Alone.” Yes!