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, 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 2
Bad Cop / Bad Cop + The Last Gang @ X-Ray Arcade
Tirelessly touring and insanely awesome Fat Wreck Chords’ act Bad Cop / Bad Cop returns to X-Ray Arcade for the third time to head up a June 2 show that also features The Last Gang. Yes!

Saturday, June 3
The Trusty Knife + Crappy Dracula, The Steph Lippert Project @ Promises
The Trusty Knife existed in that weird pre-streaming, pre-Bandcamp, pre-Soundcloud era of DIY Milwaukee music. Burnt CDs were the order of the day, sold mostly at shows and prone to eventual misplacement and deterioration. The Trusty Knife’s self-titled debut was released in this format in 2008; aside from a small run of 7-inch records for single “Natural Habitat,” that was it. Fast-forward to 2020, when Dusty Medical Records plucked the album from near-obscurity, treated it to a Justin Perkins remastering, put it on modern streaming services, and reissued it on a vinyl LP. “Timeless pop music from one of the great overlooked bands of 2000s-era American Indie Rock,” reads the Dusty Medical description, which is spot-on.

Saturday, June 3 and Sunday, June 4
Taylor Tomlinson @ Riverside Theater
You’d be hard-pressed to find a modern comedian whose ascent has been faster than that of Taylor Tomlinson. The jump from clubs to multi-night theater residencies is well-deserved, as the young comic has put in the work in order to craft well-written, identifiable, and uproariously funny material that finds her on the verge of mainstream stardom. Tomlinson will be coming to Milwaukee in early June for three shows at Riverside Theater spread over two nights.

Tuesday, June 6
Shea Day with Field Report + Dramatic Lovers, Long Mama, DJ Caleb Westphal @ Cactus Club
On Tuesday, June 6, an amazing lineup of local musicians will take the stage at Cactus Club to show their appreciation for the Milwaukee music super supporter Shea Frevele (and also celebrate her birthday) during a “Shea Day” concert. This display of Shea-centric gratitude will be headlined by Field Report, who will treat Milwaukee to a rare full-band performance in a club setting. In addition to Field Report’s presence, Dramatic Lovers will play one of its final concerts of 2023 and Long Mama will open things up with a trio set featuring its founding members. DJ Caleb Westphal will also spin 45s before the show, after the show, and between bands.

Death Cab For Cutie + Lomelda @ Riverside Theater
Almost a full year removed from performing at Summerfest, seminal indie rock outfit Death Cab For Cutie will return to Milwaukee to play at Riverside theater in belated support of its tenth studio album, Asphalt Meadows. Lomelda opens.

Friday, June 9
Immortal Girlfriend + Lila Realm, MATTHÚ @ Cactus Club
Immortal Girlfriend doesn’t play out too much these days. So when you have a chance to see the outstanding Milwaukee sibling synth duo perform, you shouldn’t miss it. And when Lila Realm (a side project of Amanda Huff) and MATTHÚ (a side project of Immortal Girlfriend’s Kevin Bush), and this loaded Cactus Club bill is a certified can’t-miss affair.

Friday, June 9 and Saturday, June 10
Bobcat Goldthwait @ The Laughing Tap
Bobcat Goldthwait is coming to The Laughing Tap! Yes, the legendary comedian, actor, director, and documentarian will return to the cozy Walker’s Point comedy club June 9-10 for two nights of stand-up. If you want to see Bobcat perform in an intimate Milwaukee venue, we highly recommend you act soon because tickets to these three shows are moving fast.

Saturday, June 10
Chicken Shack Rye Release and Bluegrass Bonanza @ Great Lakes Distillery
Great Lakes Distillery and WMSE are joining forces for the second consecutive year to release Chicken Shack Rye. This June 10 bottle release event will double as a full-fledged Bluegrass Bonanza, as Horseshoes & Hand Grenades and Chicken Wire Empire will perform in the distillery’s parking lot. There will also be food, Central Waters beer, and a wide range of craft cocktails on hand during this outdoor affair.

Escape From Wiscansin Fest with T-Pain, Chance The Rapper, Chlöe, Afroman, and more @ The Rave/Eagles Club
After headlining the inaugural Wiscansin Fest at The Rave last June, T-Pain is returning to the same Milwaukee venue almost exactly a year later for another one-day spectacle. Yes, on Saturday, June 10, “Escape From Wiscansin Fest” will find world-renowned singer, rapper, and producer taking the The Rave/Eagles Club stage again. This time around, he’ll be joined by Chance The Rapper, Chlöe, Afroman, DJ Paul (of Three 6 Mafia fame) and a wealth of other rappers and DJs.

Tuesday, June 13
The Flaming Lips @ Riverside Theater
Along with 1999’s Soft Bulletin, 2002’s Yoshimi Battles The Pink Robots elevated The Flaming Lips from quirky ’90s oddities to (still-quirky) 21st century stars. It’s easy to see/hear why: “Fight Test,” “Do You Realize??” “All We Have Is Now,” and the title track are all gorgeous psych-rock creations, and among the best songs ever devised by Wayne Coyne and company. So wouldn’t it be great to hear the band play Yoshimi live in concert? Well, it’s happening, on Tuesday, June 13 at Milwaukee’s Riverside Theater.

Friday, June 16
Pansy Division + Bev Rage & The Drinks, Rat Bath @ X-Ray Arcade
Groundbreaking queercore pioneers Pansy Division will come to Cudahy to play material from its influential seven-album, 30-year career at X-Ray Arcade. Joining “the first openly gay rock band” is Bev Rage & The Drinks, and lauded local outfit Rat Bath.

Friday, June 16 and Saturday, June 17
Sam Tallent @ The Laughing Tap
Colorado comedian Sam Tallent has toured relentlessly across North America and Europe, amassed TV credits on Comedy Central and Viceland, and his debut novel (Running The Light) has garnered favorable reviews from literary critics and inspired kind words from fellow comics like Marc Maron and Ron White. Tallent also holds the distinction of headlining The Laughing Tap’s first weekend in business. Now, he returns to the Walker’s Point club he helped christen in very early 2020 for a trio of performances running June 16-17.

Wednesday, June 21
Counting Crows + Dashboard Confessional @ Miller High Life Theater
It’s been a long spring, but there’s reason to believe maybe this season will be better than the last. Counting Crows will kick off summer in style by playing songs from its hit-laden catalog that spans more than 30 years. Need another reason to come out? Okay! Dashboard Confessional will be opening.

Milwaukee Record presents ‘Starship Troopers’ @ Avalon Theater
Has any modern-ish movie been more misunderstood than Starship Troopers? Decried by critics as a dirt-dumb glorification of fascism and jingoism upon its 1997 release, the film has since been celebrated as a satire of fascism and jingoism. Wanna see this big-bug satire on the big screen? You can on Wednesday, June 21, when we’ll screen a 4K restoration of Starship Troopers at the Avalon Atmospheric Theater! Young people from all over the globe are joining up to fight for the future. Do your part, and get your tickets NOW.

Friday, June 23 through Sunday, June 25
Bill Bellamy @ Milwaukee Improv
Actor, longtime MTV VJ, alleged creator of the term “booty call,” and veteran comedian Bill Bellamy will drop by the Milwaukee Improv in nearby Brookfield to treat the suburban club to a total of five performances spread across three nights. Be there or, well, probably be at the first weekend of Summerfest.

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