Remember when the end of summer was also kinda-sorta a signal for things slowing down in Milwaukee entertainment? Those were simpler (and much more boring) times. Thankfully, there are also a ton of musicians, comedians, and wrestling variety shows coming to traditional venues during the first full month of fall. And that’s not even counting recurring Milwaukee Record events like our Halftime Show concert series, the return of Midweek Music, and a bunch of other fall festivals. As you get ready to have an awesome autumn, here are 15 of Milwaukee Record’s October event picks. Check our Calendar section for more recommended events.

Wednesday, October 5
The Roast Of Milwaukee @ The Cooperage
After a couple of years away, 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. Joining the homegrown humorists is host Kristin Brey of “As Goes Wisconsin,” as well as a handful of surprise guests. 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 7
Chris Gethard @ X-Ray Arcade
Chris Gethard is a lot of things. He’s a cult comedy legend, the namesake and former figurehead of The Chris Gethard Show, an actor (who you might know from films like Don’t Think Twice and TV shows like Broad City and The Office), the host of the Beautiful/Anonymous podcast, an avid soda pop collector, and an undisputed point of New Jersey pride. He’s also going to be performing two shows in Cudahy this fall. Gethard will come to X-Ray Arcade on Friday, October 7, where he’ll perform two shows with two different formats. The early show will be a live recording of his aforementioned Beautiful/Anonymous podcast. The late show will feature Gethard performing stand-up comedy. Both events are all ages.

Steven Wright @ South Milwaukee Performing Arts Center
Often imitated and never replicated, Steven Wright is the master of the one-liner. The veteran comedian has helped revolutionize the art of stand-up with his surrealist and deadpan style and monotone delivery that have been delighting audiences for decades. The legendary humorist will make a rare appearance in the area when he swings by South Milwaukee Performing Arts Center for what’s sure to be an unforgettable and side-splitting show.

Saturday, October 8
Comedian CP @ Potawatomi Hotel & Casino
Wait, Ned from Detroiters—better known as Christopher Powell or “Comedian CP”—is coming to Milwaukee to perform stand-up? Awesome! The actor and comedian who you might know from Empire, Love Life, and from his recurring role in the criminally underrated Detroiters will headline a pair of shows at the Northern Lights Theater on Saturday, October 8. While you wait for these shows, watch him steal scenes throughout the “Hog Riders” episode of Detroiters.

Flannel Fest @ Boone & Crockett / The Cooperage
Back in 2019, Boone & Crockett—in partnership with The Cooperage, Taco Moto, and Pedal Tavern—hosted a celebration of music, food, and seasonal attire known as “Flannel Fest.” That iteration brought hundreds of people to the Harbor District bar on a brisk fall day/night to see live music performances. We were there. It was fun! Boone & Crockett will officially be bringing Flannel Fest back in a live and in-person capacity on Saturday, October 8. This time around, Boone & Crockett’s parking lot will host a wide range of Milwaukee-based artists. You can see the eclectic and altogether impressive Flannel Fest lineup HERE.

Sunday, October 9
The Mars Volta + Teri Gender Bender @ The Rave / Eagles Club
The Mars Volta is coming to The Rave / Eagles Club on Sunday, October 9. That’s pretty much all you need to know, right? You should go to this. Teri Gender Bender opens.

Peter Mulvey + SistaStrings @ The Back Room @ Colectivo
In late 2020, prolific singer-songwriter Peter Mulvey and the incomparable instrumentalists in SistaStrings co-released Live At The Cafe Carpe, a live album the accomplished artists recorded at the eponymous Fort Atkinson, Wisconsin cafe in pre-pandemic times. Almost two years removed from that record’s release, Mulvey—a Milwaukee-born musician who now calls Massachusetts home—and the Ross sisters—a Milwaukee mainstay who are enjoying tremendous amounts of success following a recent move to Nashville—once again collaborated on a joint album. A few months removed from the release of Love Is The Only Thing, Mulvey and SistaStrings will return to their hometown to perform songs from their two albums.

Sunday, October 16
Dru Hill + SWV, Dave Hollister @ Riverside Theater
Celebrate Sweetest Day a day late with a potent trio of R&B favorites. This Riverside concerts features headliner Dru Hill (who is celebrating its 25th anniversary), as well as SWV and Dave Hollister. Show your significant other “How Deep Is Your Love” and say “I Love You” to them by taking them to this concert.

Thursday, October 20
NNAMDÏ + Joshua Virtue @ Cactus Club

When you have a chance to see Chicago singer, rapper, producer, and multi-instrumentalist NNAMDÏ in an intimate setting like the Cactus Club, you go. Don’t mess this up, Milwaukee. Joshua Virtue opens.

Thursday, October 20 to Sunday, October 23
Jon Lovitz @ Milwaukee Improv
Actor, comedian, Saturday Night Live cast member, former Subway pitchman, and Jay Motherfucking Sherman himself Jon Lovitz is coming to Milwaukee Improv in Brookfield for a total of four performances spread across as many nights. Jon Lovitz is coming to metro Milwaukee…and we’re reaping all the benefits.

Monday, October 24
Dessa + Open Mike Eagle @ Shank Hall
Dessa can do it all. In addition to forging an amazing career as a singer, rapper, composer, and songwriter (who has been part of more than a few Billboard-charting hits), the multi-faceted Minneapolis musician is also a skilled writer who has been published in a variety of respected national publications. But back to the music stuff: Dessa will swing by Shank Hall on Monday, October 24 for a somewhat rare Milwaukee performance. Open Mike Eagle, a versatile entertainer in his own right, will also perform.

Friday, October 28
Mondo Lucha @ Turner Hall
Since starting in 2008, Mondo Lucha has brought high-flying wrestling action, burlesque dancers, and live music to its annual Turner Hall showcase. Along the way, the variety show has managed to work with renowned pro wrestlers, sell out numerous shows, and become a must-attend Milwaukee event. The beloved local variety show returns to its familiar ballroom haunt on Friday, October 28.

Saturday, October 29
Mightmare + Rat Bath, Kat And The Hurricane, Dandy L. Freling @ Cactus Club
If you love Sarah Shook, you might also enjoy Mightmare, their decidedly-less-country-tinged new project. Shook’s new venture will come to the familiar confines of Milwaukee’s Cactus Club in belated support of their debut Mightmare album, Cruel Liars.

Sunday, October 30
The Smashing Pumpkins + Jane’s Addiction, Poppy @ Fiserv Forum
Tonight, tonight (well, on October 30, actually)! You can party like it’s 1979 (well, more like it’s 1996, when “1979” came out) in Milwaukee when The Smashing Pumpkins headline Fiserv Forum. This loaded lineup also features Jane’s Addiction and Poppy.

Goblin (‘Suspiria’ Live Score) @ Oriental Theatre
Back in 2018, Milwaukee moviegoers were treated to a screening of Dario Argento’s 1977 classic giallo film Suspiria at the Oriental Theatre. But it wasn’t just any screening—it came complete with a live score from Italian progressive rock band Goblin and founding keyboardist Claudio Simonetti, both of whom provided the iconic original score to the film in the first place. If you missed that event, you’re in luck, because Suspria, Goblin, and Simonetti are set to return to the Oriental on Sunday, October 30. Halloween Eve!