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 last weekend, which gives way to PrideFest, Locust Street Festival, Summer Soulstice, and much of Summerfest. Meanwhile, a bundle of concert series like Chill On The Hill, Jazz In The Park, and Third Space Presents 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.

Friday, June 7
Le Freak Reunion @ Boone & Crockett
From its 2012 origin through 2016, the recurring Le Freak dance party series brought great music, top-notch visuals and photography, community, and pizza to Hotel Foster (R.I.P.) and Company Brewing (R.I.P.). On Friday, June 7, the gang is getting back together for a long-awaited Le Freak Reunion out on the Boone & Crockett patio from 8 p.m. to 1 a.m. It could be another eight years before this happens again, so don’t miss your chance to experience Le Freak one more time.

Friday, June 7 and Saturday, June 8
Laurie Kilmartin @ The Laughing Tap
Back in 2022, accomplished comedian, longtime Conan staff writer, and best-selling author Laurie Kilmartin headlined Milwaukee Comedy Festival’s finale, which took place at Shank Hall. The veteran comic set up shop at The Laughing Tap last May, and she’ll return to the Walker’s Point comedy club for a total of four shows spread over two nights.

Saturday, June 8
Collections Of Colonies Of Bees + Immortal Girlfriend, EXITSTATEMENTS @ Vivarium
Since opening in late February, Vivarium has wasted little time filling the new East Side venue with impressive bookings on both the national AND local scale. This downright wonderful trio of homegrown projects—Collections Of Colonies Of Bees, Immortal Girlfriend, and Exit Statements—taking the Vivarium stage on Saturday, June 8 is a perfect example of the latter.

Maggie Rogers + The Japanese House @ BMO Pavilion
While PrideFest is raging on the other side of the Henry Maier grounds on June 8, Grammy-nominated indie-pop prodigy Maggie Rogers will be performing at the BMO Pavilion as part of her Don’t Forget Me Tour. The Japanese House opens.

T-Pain’s Wiscansin Fest @ The Rave / Eagles Club
For the third straight June, world-renowned singer, rapper, and producer T-Pain will be coming to The Rave/Eagles Club to headline his Wiscansin Fest. This year’s installment features accompaniment by Akon, Dillon Francis, Pink Sweat$, Soulja Boy, LaRussell, Ying Yang Twins, Yelawolf, Waka Flocka Flame, Flyana Boss, Myaap, Young Ca$h, Chayo Nash, NandoSTL, DJay Mando, and more.

Wednesday, June 12
Wilco + Cut Worms @ Riverside Theater
Wilco is coming to Milwaukee’s Riverside Theater on Wednesday, June 12. It’s going to be awesome. Cut Worms will open the show. What more needs to be said? Nothing. Go to this.

Thursday, June 13
Pete Davidson @ Riverside Theater
You either get Pete Davidson or you don’t. “He’s just Pete,” reads a Pete Davidson press release. Yep, it’s as simple as that! And now Milwaukee will get a chance to get Pete Davidson (or not) in person when the comedian, actor, and former Saturday Night Live star makes his Riverside Theater debut on Thursday, June 13 (rescheduled from January 4) as part of his Prehab Tour.

Saturday, June 15
Joe Pera: The Peras Tour @ Pabst Theater (and “Warm Apple Nights” Pop-Up @ Sugar Maple June 13-16)
Hello. Joe Pera—the former star and namesake of the incredible Adult Swim series, Joe Pera Talks With You—is returning to Milwaukee (where the majority of the show was filmed) on Saturday, June 15 to perform comedy at the Pabst Theater. The show will be part of the inimitable comedian’s ongoing “The Peras Tour.” His Milwaukee return has also inspired us to work with The Sugar Maple to do the four-day “Warm Apple Nights: A ‘Joe Pera Talks With You’ Pop-Up” at the Bay View bar.

Monday, June 17
Camp Trash + exciting!!excellent!!, Barely Civil, Doubter @ Cactus Club
Who says Mondays have to be bad? Start the week in grand fashion with a downright impressive Cactus Club bill that features the Florida-forged indie rock stylings of Camp Trash, exciting!!excellent!! from Portland, and local support from Barely Civil and Doubter.

Friday, June 21
Direct Hit! + So Zuppy, Bad Crime, Death Killer Overdrive @ Anodyne Walker’s Point Roastery
Doesn’t it feel like it’s been forever since Direct Hit! played a hometown show? Well, it has been a while since the Fat Wreck Chords-approved Milwaukee pop-punk phenoms played in the area, so don’t miss this opportunity to catch Direct Hit! (and So Zuppy, Bad Crime, and Death Killer Overdrive) at Anodyne’s Walker’s Point Roastery on June 21.

Friday, June 21 and Saturday, June 22
They Might Be Giants @ Pabst Theater
How does the old saying go? “No one in the world ever gets what they want, and that is beautiful”? Yeah, that’s it. Who said that again? Oh yeah, it was They Might Be Giants! And why are we bringing up the ever-delightful, fantastic-as-always alt/geek-rock duo of John Flansburgh and John Linnell? Because they’re coming to Milwaukee’s Pabst Theater for a two-night engagement, Friday, June 21; and Saturday, June 22! Turns out you can get what you want, and that, too, is beautiful! Well, as long as you bought tickets in time. These shows—which we’re thrilled to say are presented by Milwaukee Record—are both sold out.

Wednesday, June 26
Milwaukee Record presents ‘Happy Gilmore’ @ Avalon Theater
On Wednesday, June 26, we’re showing ‘Happy Gilmore’ at Avalon Theater. This classic mid-’90s comedy stars Adam Sandler has the titular Happy Gilmore, a wannabe hockey player with a hot temper. When he learns his grandmother’s tax problems have her on the brink of losing her home, Gilmore—known for his powerful-yet-erratic slap shots—reluctantly picks up golf and joins the pro tour in hopes his long drives will help him earn enough money to save the house.

Along the way, this goon-turned-golfer faces off against Shooter McGavin (played by Christopher McDonald in a career-defining role), is mentored by Chubbs Peterson (the late, great Carl Weathers), and falls for Virginia Venit (Julie Bowen). There are also unforgettable cameos by Ben Stiller, Kevin Nealon, Joe Flaherty, Richard Kiel, and that iconic interaction with Bob Barker. Are you too good to watch the 1996 sports comedy ‘Happy Gilmore’ with us at Avalon Theater on Wednesday, June 26? ANSWER ME!