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 other entertainers coming to town during the first full month of fall. And that’s not even counting recurring Milwaukee Record events like our Halftime Shows, the Midweek Music concert series, and an abundance of fall festivals. There are a bunch of great shows coming to Milwaukee in October, but here are 15 standouts from the bunch.

Monday, October 2
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. Joining the homegrown humorists is host Ted Perry of FOX6 fame, 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.

Thursday, October 5
The Eric Andre Explosion @ The Rave / Eagles Club
With his unmatched energy and penchant for taking his comedy to unpredictable, uncomfortable, and occasionally even dangerous places, Eric Andre has fashioned a career through forcing audiences to expect the unexpected. This is best (and most famously) displayed on The Eric Andre Show and 2021’s Bad Trip. Beyond his work in TV and film, Andre also occasionally hits the road for live show experiences. One such live show will take place at The Rave / Eagles Club when “The Eric Andre Explosion” comes to Milwaukee for what’s sure to be a crazy night.

Saturday, October 7
Beet Street Harvest Festival @ Cactus Club
The 8th annual Beet Street Harvest Festival will take place on Saturday, October 7. The Bay View block party—hosted by Cactus Club, Palomino, and Goodkind—is set to bring about a day of live music, local food and retail vendors, and pie-based competition to a parcel of Wentworth and Potter avenues. The family-friendly event will run from 2-8 p.m., with an 18+ after party to take place at Cactus Club once Beet Street concludes.

Kyle Kinane @ Pabst Theater
Beloved comedian, actor, and Illinois native Kyle Kinane will return to the Midwest to take the stage at Pabst Theater on Saturday, October 7 as part of the Milwaukee Comedy festival. Tickets to this show—Kinane’s first Milwaukee appearance since late 2019—are running low, so act fast!

Ratboys + Free Range @ The Back Room @ Colectivo
Being from Chicago and all, Ratboys is no stranger to playing Milwaukee. This time around, the up-and-coming indie project is heading to The Back Room @ Colectivo to perform in support of its latest and greatest album, the just-released The Window, after Free Range opens things up. Whether you’ve seen some of the band’s Cactus Club shows in recent years or you’re just hopping aboard the bandwagon now, don’t miss this opportunity to see Ratboys in a relatively intimate venue because it seems like even bigger things are on the way for them (and soon!).

Sunday, October 8
Jonathan Richman @ Marcus Performing Arts Center
Bless you, Jonathan Richman. The legendary singer-songwriter has been a force of good and wide-eyed whimsy since the early 1970s, back when he was with The Modern Lovers. These days, his acoustic shows (usually with drummer Tommy Larkins) are welcome escapes from a world of noise and chaos. He was in There’s Something About Mary. We once interviewed him via fax. He and Larkins are set to play the Marcus Performing Arts Center on Sunday, October 8.

The Beaches @ The Cooperage
Less than a month removed from releasing its latest album, the excellent Blame My Ex, Canadian rock outfit The Beaches will swing through Milwaukee to play a show at The Cooperage.

Janelle James @ Pabst Theater
From Thursday October 5 through Thursday, October 12, Milwaukee Film’s 2023 Cultures & Communities Festival will take over the Oriental Theatre—and much of the city itself. The “eight-day convergence of groundbreaking films, distinguished speakers, and public forums designed to amplify diverse cultural expressions and celebrate community” will include a host of city-wide parties, panel discussions, a “sneaker and streetwear summit,” and even a stand-up set from Abbott Elementary star and accomplished comedian Janelle James, who will take the stage at Pabst Theater on Sunday, October 8.

Bill Burr @ Fiserv Forum
Veteran comedian, actor, writer, podcaster, hockey fan, helicopter pilot, amateur drummer, and consummate Milwaukee fan Bill Burr will perform at Fiserv Forum on Sunday, October 8. “This event will be a phone-free experience,” reads a press release. “The use of phones, smart watches and accessories will not be permitted in the performance space.” So check those phones before Burr checks in on us.

Tuesday, October 10
Bonnie Raitt @ Riverside Theater
What’s there to say? Bonnie Raitt is a legend!

Wednesday, October 11 and Thursday, October 12
Bob Dylan @ Riverside Theater
Bob Dylan! Two nights at Milwaukee’s Riverside Theater! The last time we saw Dylan live (way back in 2015) he was pretty great! And hopefully he’ll be pretty great again when he plays these shows, which are part of his “Rough And Rowdy Ways” tour. (The album of the same name was released in 2020; it’s the one with the 17-minute song about JFK.)

Thursday, October 12
Lucinda Williams And Her Band @ Pabst Theater
With 17 outstanding albums, three Grammys, immeasurable artistic influence, and an ever-evolving sound she’s graciously shared with audiences all over the world throughout her 45-year career, it’s safe to say Lucinda Williams is nothing short of legendary. Don’t miss your opportunity to see the incomparable singer-songwriter when she comes to the Pabst Theater on Thursday, October 12.

Friday, October 20 through Sunday, October 22
Widespread Panic @ Riverside Theater
you can always depend on a few things: death, taxes, and legendary Athens jam band Widespread Panic selling out Milwaukee’s Riverside Theater over multiple dates. If you can manage to score tickets, you can catch the group at one of three shows from October 21-23.

Sunday, October 22
Carmen Christopher + Raegan Niemela @ Cactus Club
Actor, writer, and comedian Carmen Christopher will come to Cactus Club on Sunday, October 22 for what’s sure to be a hilarious evening of off kilter comedy as part of his ongoing “The Waverunner Stand Up Comedy Tour.” If Christopher’s name doesn’t immediately ring a bell, you probably recognize him from his appearances on shows like The BearI Think You Should Leave, Killing It, Shrill, and Joe Pera Talks With You. Speaking of Pera, some of you probably remember Christopher as the opener for Joe Pera’s pair of shows at The Back Room @ Colectivo in April 2022. Milwaukee’s own Raegan Niemela will open things up.

Tuesday, October 31
Shania Twain @ Fiserv Forum
Where do you start with Shania Twain? We could mention her five Grammy Awards or the millions upon millions of albums sold. We could acknowledge her crossover country appeal long before that was commonplace in mainstream music. We could simply talk about how she’s incredibly talented and her abundance of hits have endured for decades at this point. Whatever your preferred hook is, you’re probably happy to know she’ll be coming to Milwaukee to treat Fiserv Forum material from her incomparable career on Tuesday, October 31 as part of her “Queen Of Me” tour.