Our fat-free, dolphin-safe Milwaukee events calendar is chock-full of things to do, but only a handful of events are worthy of the lofty honor of “Record Recommended” (patent pending). Here are our recommendations for September 7-12, 2021.

Tuesday, September 7

Chill On The Hill: Fressure Point + Fuzzysurf @ Humboldt Park
Can you believe that Chill On The Hill is almost over? Fortunately, this Humboldt Park concert series saved some of its best installments for the tail end of the series. Chill’s penultimate performance of 2021 features the likes of Fressure Point and the summer-suited sounds of Fuzzysurf. The free and family-friendly fun begins at 6:30 p.m. Break out those lawn chairs, Milwaukee!

Wednesday, September 8

Jonas Brothers + Kelsea Ballerini + Spencer Sutherland @ American Family Insurance Ampitheater
It’s the “Remember This” tour! With the Jonas Brothers! For one of Summerfest’s not-quite-Summerfest “Wednesday Kick-Off” shows at American Family Insurance Amphitheater! Be there!

Thursday, September 9

Summerfest (Weekend #2) @ Henry Maier Festival Park (through September 11)
Hey! Summerfest 2021 is happening September 2-4, 9-11, and 16-18. (There are also some amphitheater-only “Wednesday Kick-Off” concerts.) Find the full lineup for every day and every stage HERE. And remember: you’ll need to provide proof of a COVID-19 vaccination or a negative COVID-19 test to enter!

Rainbow Summer: DLC Dance @ Marcus Center Grounds
After a few months of concerts, film screenings, and other types of family-friendly entertainment, Marcus Center’s “Rainbow Summer” series is nearing its end. The second-to-last performance finds DLC Dance taking to the Peck Pavilion for a free Thursday night show.

In The Pines + Rookie + Motel Breakfast @ Cactus Club

Friday, September 10

Sad Summer Festival @ The Rave/Eagles Ballroom
Something this sad never sounded so good. The Rave/Eagles Ballroom will play host to a so-called “Sad Summer Festival” that features performances by All Time Low, The Story So Far, Movements, The Maine, Grayscale, and Destory Boys.

D.L. Hughley @ Milwaukee Improv
The Hughley Show namesake, one of the “Original Kings Of Comedy” and veteran stand-up D.L. Hughley will break in the Milwaukee Improv when he performs five shows in the new Brookfield-based club September 10-12.

Matty Ryan @ The Laughing Tap
Not to be confused with the overrated Atlanta Falcons quarterback by the same name, this Matty Ryan is an actor, comedian, voiceover professional, and guy we once saw crush while featuring for Brooks Wheelan in Madison a few years back. The Chicago-born Ryan will return to the Midwest to headline two shows at The Laughing Tap September 10-11.

Bianca Del Rio @ Pabst Theater

Jo Koy @ Riverside Theater

Kathleen Edwards @ The Back Room @ Colectivo

Saturday, September 11

An Evening With Steve Wynn @ URSA
Over the course of his extensive and impressive career, Steve Wynn has released more than 30 albums that are spread between his solo endeavor, The Dream Syndicate, and The Baseball Project. Along the way, he’s performed to audiences of all sizes all over the world, toured with the likes of U2 and R.E.M., composed scores for television and film, and spent time on a major record label. This month finds Wynn embarking on a solo tour that will bring him to a variety of intimate performance spaces, such as homes, yards, record stores, and (in the case of his September 11 Milwaukee stop) to URSA in Bay View.

Silver City International Festival @ Arlington Heights Park
Since its start in 2012, Silver City International Festival has celebrated the numerous cultures that help make Silver City the most diverse neighborhood in Milwaukee through food, the arts, and music. After taking the year off from hosting the event in its traditional sense, we’re please to report Silver City International Festival will make its triumphant return. This year’s festival will take place from noon-5 p.m. at Arlington Heights Park (3429 W. Pierce St.) on Saturday, September 11.

Iliza @ The Riverside Theater

Yves Tumor @ Cactus Club

D.L. Hughley @ Milwaukee Improv

Matty Ryan @ The Laughing Tap

Sunday, September 12

Milwaukee Record Halftime Show: Nile @ Cactus Club
After a season away, the Milwaukee Record Halftime Shows series has returned! This season, we’ve assembled a stacked roster of 17 performers that will provide FREE all-ages entertainment during halftime of Green Bay football games. Like previous seasons, our friends at Miller High Life will sponsor our football-focused festivities, meaning fans can enjoy “The Champagne Of Beers” and Miller Lite for $2.50 a bottle or $10 for a bucket of five beers all game long. Milwaukee rapper Nile will kick the season off with a Week 1 performance at Cactus Club.

Armand Hammer + CRASHprez @ Cactus Club
The year is months from being over, but it’s safe to assume Armand Hammer is responsible for making one 2021’s best albums. The rap duo joined forces with The Alchemist to make Haram, an otherworldly effort that takes their already cerebral creations to exciting, inspiring, and altogether enjoyable new territory. Celebrate a Packers Week 1 victory by heading to Cactus Club to see Armand Hammer headline this 18+ show.

SistaStrings + Sara And Kenny @ Anodyne Walker’s Point Roastery
This Sunday night event doubles as a homecoming for two acts with local ties. Tennessee (by way of Milwaukee) sibling duo SistaStrings will headline this Anodyne Walker’s Point Roastery show, which also features opening accompaniment from the Milwaukee-born (and now Chicago-based) project Sara And Kenny.

D.L. Hughley @ Milwaukee Improv