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 PrideFest, which gives way to Polish Fest, Summer Soulstice, and the majority of Summerfest. Meanwhile, a bundle of concert series like Chill On the Hill, Jazz In The Park, and Milwaukee Boat Line’s Concert Cruises begin, making every week enjoyable.

We’ve already detailed most of those in our exhaustive festival guide, but, believe it or not, there’s also a ton of non-festival shows adding to the summer-long entertainment dilemma. From established comedians to great musicians and even a conversation with the Mayor, here are Milwaukee Record’s 13 can’t-miss June events. You can find more events in our Calendar section.

Wednesday, June 1
Sigur Rós @ The Riverside Theater
Buckle up for an impossibly chill and ethereal night as Icelandic post-rock outfit Sigur Rós gently blows into Milwaukee’s Riverside Theater. The long-running group’s latest album, Odin’s Raven Magic, is an orchestral work that was initially recorded way back in 2004.

Friday, June 3
Phoebe Bridgers + Charlie Hickey @ BMO Harris Pavilion
Has singer-songwriter Phoebe Bridgers seemingly been everywhere lately? Yes she has, popping up on Taylor Swift songs and My Favorite Murder podcasts, and getting the old folks all in a tizzy by smashing a guitar on Saturday Night Live. Oh, and don’t forget that Twitter spat with David Crosby, which was hilarious. Oh, and don’t forget Bridgers’ actual music! Her latest record, Punisher, came out in 2020.

The Dollop @ Turner Hall Ballroom
In case you’re not among the show’s millions of listeners: The Dollop is a popular podcast wherein comedian Dave Anthony reads a story from American history to his friend, Gareth Reynolds, who doesn’t know what the topic is about. Only time will tell what locally focused topic they discuss during their Turner Hall return, but it’s sure to be informative, entertaining, and likely to draw parallels between how bad things were throughout history and how terrible the world continues to be today. The show is also a homecoming of sorts for Reynolds, a devout Packer Backer who originally hails from Brown Deer and got his start at ComedySportz.

Orville Peck + The Nude Party @ The Pabst Theater
Masked country music up-and-comer Orville Peck comes to The Pabst Theater, where he’ll treat Milwaukee to live versions of songs off Bronco, his just-released sophomore album. The Nude Party opens, and we’re not discounting the very real possibility of a Trixie Mattel cameo at some point as well.

Monday, June 6
PUP + Oceanator @ Turner Hall
A couple months after the release of Pup’s fourth album, THE UNRAVELING OF PUPTHEBAND, the Canadian pop-punk quartet will return to Turner Hall to play in support of that new record and dip into rousing selections from the band’s three can’t-miss predecessors. Oceanator will play in support.

Thursday, June 9
The Recombobulation Area Presents: A Conversation With Cavalier Johnson
The Recombobulation Area’s Dan Shafer will be interviewing Milwaukee Mayor Cavalier Johnson live at Boone & Crockett. Thursday, June 9. 5:30 p.m. The event is free and you can register HERE.

Saturday, June 11
T-Pain’s “Wiscansin Fest” @ The Rave / Eagles Club
In “Put you in the mansion somewhere in Wiscansin” news, T-Pain is launching an 18-date “Road To Wiscansin” tour in San Francisco on May 10. It’ll culminate June 11 at The Rave, at the so-called “Wiscansin Fest.” T-Pain will be joined by some “very special guests,” including Lil Jon, Juvenile, Hannibal Buress’ hip-hop alter ego Eshu Tune, and many more.

Sarah Sherman @ Cactus Club (two shows)
Fresh off her star-making first season as a featured cast member on Saturday Night Live, writer and comedian Sarah Sherman (a.k.a. Sarah Squirm) will showcase her stand-up skills during a pair of performances in the intimate confines of the Cactus Club. The 7 p.m. early show is an all-ages event.

Wednesday, June 15
Jeff Rosenstock @ Turner Hall
After postponing his January show, prolific ska-punk troubadour Jeff Rosenstock is coming to Turner Hall in June. If you know Jeff Rosenstock, you’re probably well aware of this and you’ve already bought your ticket. On the off chance you didn’t know about this, now you do.

Thursday, June 16
Laugh Track Cinema: ‘Aswang’ (1993) @ The Laughing Tap
Join us and Lakefront Brewery at The Laughing Tap on Thursday, June 16 for another riff-tastic celebration of Wisconsin-made movies…which is now called “Laugh Track Cinema.” This time around, there will be a screening of Aswang, a low-budget horror movie from 1993 that was filmed in various locations throughout southeastern Wisconsin and features many actors from Milwaukee. The film’s star—and a Milwaukee theater legend in his own right—Norman Moses will be on hand during intermission for a spirited chat and some good-natured ribbing. Comedians Kaitlin McCarthy, David Louis, and Norman’s daughter Kelsey Moses will handle the riffing.

Thursday, June 23 through Sunday, June 26
Lara Beitz @ Milwaukee Improv
Milwaukee-born and -raised comedian Lara Beitz (who is now based on Los Angeles) will return to her old stomping grounds June 23-26 to headline a total of six shows the Milwaukee Improv in nearby Brookfield. In recent years, the homegrown humorist has earned acclaim from Judd Apatow and David Spade, and has become the go-to feature act for Pete Holmes.

Friday, June 24
Joshua Ray Walker + Sarah Shook & The Disarmers @ Cactus Club
If you don’t know the name Joshua Ray Walker yet, you’re about to be hearing a lot about him. Since first gaining notoriety in country music circles with his 2018 debut, Wish You Were Here, the Dallas singer-songwriter has won fans all around the world and earned high praise from some of music’s most renowned publications. Walker’s sophomore album, Glad You Made It, has garnered even more acclaim and finds the up-and-coming country talent on the cusp of even bigger and better things. Walker will be joined by Sarah Shook & The Disarmers, who will return to Cactus Club a few months removed from the release of their latest album, the all-around excellent Nightroamer.

Wednesday, June 29
Milwaukee Record presents ‘Blade’ (1998) @ Avalon Theater
Before Marvel movies were MARVEL MOVIES, there was Blade. The bloody 1998 vampire-action film based on the superhero with the same name was a box office smash, a fan favorite, and the progenitor for the onslaught of comic book movies that have followed in the quarter century since its release. Blade is great and we’re screening it at Avalon Theater on Wednesday, June 29. Tickets are available NOW!