Though July comes close to matching it, there’s simply no month in Milwaukee that’s more jam-packed with entertainment than June. Festival season officially kicks off with Festa Italiana this weekend, which gives way to, Locust Street Festival, PrideFest, Summer Soulstice, and most of Summerfest. Meanwhile, a bundle of concert series like Chill On The Hill, Jazz In The Park, and Third Space’s “Under The Bridge” all begin, making every week enjoyable.
We’ve already detailed most of those things in our exhaustive Summer Festival Guide, but there’s also a ton of non-festival shows adding to the summer-long entertainment dilemma. From stacked local bills to touring talent to our monthly movie screening, there are lots of ways to enjoy June amid the festival frenzy. Here are just a few events that stand out.
Sunday, June 1
Bluebird Improv @ Turner Hall
When Bluebird—an improv collective that features all-time make-’em-up masters like Tim Meadows and Matt Walsh in its ranks—comes to your city and tickets are still available, you say yes and you go.
Monday, June 2
Peelander-Z + Fight Dice, Nasty Boys @ Cactus Club
What do you get when you combine a “Japanese Action Comic Punk” project from Austin, a D&D-themed rock band with members of Braid and The Promise Ring in its ranks, and a “Nasty” thong-donning duo from Milwaukee? You get the lineup for this can’t-miss Cactus Club bill, of course.
Friday, June 6
The Hallelujah Ward + Caley Conway @ Cactus Club
Come to Cactus Club on June 6 to celebrate the release of Everybody Swoons, the long-awaited album from the Mark Waldoch-fronted The Hallelujah Ward. He’ll be joined on the bill by Milwaukee music mainstay Caley Conway. Speaking of local treasures, this show doubles as the birthday party for certified local treasure Shea Frevele.
Saturday, June 7
Todd Barry @ Shank Hall
With more than 40 years of stage time beneath his belt along with an often-imitated, never replicated wry and soft-spoken comedic style, Todd Barry is on the fringe of comedy legend status. Barry—who has been a recurring visitor to Milwaukee in recent years, including a couple of Milwaukee Comedy Festival appearances—will come back to town to head up a show at Shank Hall on Saturday, June 7.
Sunday, June 8
Chastity Washington @ Milwaukee Improv
Roughly two years removed from the release of her Live At Dandy Amazon special, Milwaukee’s funniest human will be live in nearby Brookfield when she headlines a show at Milwaukee Improv.
Friday, June 13 and Saturday, June 14
Oops…All Headliners! @ The Laughing Tap
After more than five fruitful and largely hilarious years in its current Walker’s Point digs, The Laughing Tap is closing down…for a few months. Before they spend the summer moving into a new spot (we’ll have more on that eventually), they’re saying goodbye with a few June shows. Excluding a June 18 open mic, the last performers to take their stage will be a stacked cast of local comics that will take part in a two-night, two-show “Oops…All Headliners!” bill. See some of the city’s best stand-ups and say farewell to The Laughing Tap (for now).
Friday, June 13
Peter Mulvey + Trapper Schoepp @ Anodyne Walker’s Point Roastery
Over the course of his 35-year music career, Peter Mulvey has released more than 20 albums, written hundreds of songs, played thousands of shows all over the world, shared bills with a wealth of notable performers, and helped to enact change though his efforts as an activist and environmentalist. Before the Massachusetts-based singer and songwriter was gathering experiences and sharing his perspective with audiences spread far and wide, he was growing up in Milwaukee. He’ll return to his hometown to perform at Anodyne’s Walker’s Point Roastery on Friday, June 13.
Saturday, June 14
T-Pain’s “Back To Wiscansin Fest IV” at The Rave / Eagles Club
In 2022, singer, rapper, and producer T-Pain embarked on an 18-show jaunt he called his “Road To Wiscansin” tour. That run of shows culminated with a show at The Rave/Eagles Club, which was dubbed “Wiscansin Fest” a day. The next Junes, T-Pain kept coming back to Milwaukee. The fourth annual installment (called “Back To Wiscansin Fest”) is scheduled to take place on Saturday, June 14. This time around, the worldwide sensation will be joined by the likes of Feid, Keyshia Cole, Pusha T, Wale, Jermaine Dupri, DJ Diesel (Shaq’s DJ alias), NLE Choppa, Kash Doll, Dreezy, Prof, Durand Bernarr, Armani White, Milwaukee’s own DJay Mando and NilexNile, and more.
Wednesday, June 18
Old 97’s + Ladybird @ Tosa Tonight (Hart Park, Wauwatosa)
On Wednesday, June 18, Tosa Tonight will kick off its 25th anniversary season by welcoming Old 97’s to the Hart Park Rotary Pavilion. The legendary and long-running Texas outfit will come to Wauwatosa in belated support of its 13th album, 2024’s American Primitive. As if a free outdoor performance by a seminal alt-country mainstay isn’t already good enough, the 97’s will also be joined on the bill by Milwaukee’s own Ladybird, who will start things off at 6 p.m.
Milwaukee Record presents ‘Real Genius’ @ Avalon Theater
Think of Real Genius as an elevated “slobs vs. snobs” ’80s flick. The late, great Val Kilmer plays Chris Knight, a brilliant laser physics student and wise-cracking slacker at the fictional Pacific Tech University. Joined by young freshman prodigy Mitch (Gabriel Jarret), he applies his talents to the top secret pet project of Professor Jerry Hathaway (go-to ’80s heel William Atherton). But when the true nature of the project is revealed, the boys rebel. Hi-tech hijinks, endlessly quotable lines, memorable turns from Michelle Meyrink and Jon “Uncle Rico From Napoleon Dynamite” Gries, and a truly silly/transcendent ending ensue.
Saturday, June 21
Insane Clown Posse + JCW Wrestling @ The Rave / Eagles Club
It’s hard to believe now, but there was a moment when the most outrageous thing in pop culture was a song in which two rapping clowns from Detroit questioned the inner workings of magnets. “Fucking magnets, how do they work?” asked the Insane Clown Posse in 2010’s instantly infamous “Miracles.” We may never know how magnets work (or solar eclipses, vicious weather, and 15,000 Juggalos together), but we’d sure love to go back to a time when the question was the only thing occupying our minds. And maybe we can, because ICP— a.k.a. Violent J and Shaggy 2 Dope—will play The Rave / Eagles Club on June 21, and they’re bringing JCW with ’em.
Tuesday, June 24 and Wednesday, June 25
Kyle Kinane @ Vivarium
Beloved comedian, actor, and Illinois native Kyle Kinane will return to the Midwest to take the stage at Vivarium on Tuesday, June 24 and Wednesday, June 25. Tickets to this show—Kinane’s first Milwaukee appearance since headlining the Milwaukee Comedy Festival is 2023—are running low, so act fast!
Wednesday, June 25
Jason Isbell And The 400 Unit @ Riverside Theater
Alt-country powerhouse and one of modern music’s finest songwriters Jason Isbell returns to the familiar confines of Riverside Theater along with his 400 Unit backing band for an early summer show in support of his months-old album Foxes In The Snow.