Believe it or not, we’ve somehow already reached the last month of 2021. This year was pretty terrible for so many people, but at least it was still noticeably better than the previous year was. Hopefully that trend of gradual improvement within an unending nightmare that is contemporary existence will continue in 2022, but we’re not going to hold our breath.

Anyway, here are 15 standout concerts, comedy shows, film screenings, maker fairs, and holiday spectacles that are happening in and around Milwaukee in December.

Thursday, December 2
Jason Isbell And The 400 Unit + Strand Of Oaks @ 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 and opener Stand Of Oaks for an early-December show in belated support of last year’s outstanding Reunions.

METZ + Preoccupations, Facs @ The Back Room @ Colectivo
Don’t forget to bring those earplugs because you’ll need ’em when METZ, Preoccupations, and Facs test the limits of The Back Room’s P.A. system during this likely loud and undeniably loaded Thursday night affair.

Sunday, December 5
Hover Craft 2021 @ Pritzlaff Building
Since 2009, Hover Craft has brought skilled local artists, crafters, retailers, and others residing beneath the broad “maker” umbrella together to bring Milwaukee-made goods to area consumers during the holiday season. Like pretty much every event happening in or around the city, Hover Craft canceled its 2020 event on account of COVID-19 concerns. However, it returns to the Pritzlaff Building on Sunday, December 5 from 12-6 p.m. Like other recent years, more than 100 vendors will partake in the Hover Craft festivities. Admission is $5. Kids get in free. Check out the full vendor list HERE.

Arlo McKinley @ The Back Room @ Colectivo
If you haven’t heard of Arlo McKinley yet, you should know he comes with John Prine’s seal of approval. Before Prine’s heartbreaking death last year, the legendary folk singer handpicked McKinley to join his Oh Boy Records label, an honor granted to only a handful of musicians over the last couple of decades. Last August, McKinley released Die Midwestern on the independent label, and his follow-up to 2014’s self-titled debut has received high praise from music media and fans ever since. After his 2020 Back Room show was postponed, McKinley will finally be able to make up the gig when he comes to the Prospect Avenue Colectivo on Sunday, December 5.

Tuesday, December 7
WMSE Local/Live Holiday Show: Caley Conway @ Anodyne Walker’s Point Roastery
Tireless Milwaukee musician Caley Conway is fresh off the release of her excellent Bliss Or Bust EP. For this show, however, expect some holiday classics like “Jingle Bells,” “Have Yourself A Merry Little Christmas,” and “Silver Bells,” all from her 2020 holiday album Heart Be Light. WMSE will broadcast Conway’s show as part of its weekly Local/Live series.

Wednesday, December 8
Chris Isaak Holiday Tour @ Miller High Life Theatre
Is Chris Isaak a Christmas artist? Does that question grow exponentially more confusing when you consider this is the guy behind such hot-and-heavy songs/videos as “Wicked Game” and “Baby Did A Bad Bad Thing”? (Answers: sure, YES.) Anyway, Chris Isaak rules. See his Holiday Tour at the Miller High Life Theatre.

Thursday, December 9
Emily Wolfe + Kiss The Tiger @ Cactus Club
If you don’t know the name Emily Wolfe yet, you will soon. The Austin-based singer, songwriter, and guitarist is a few months removed from the release of Outlier, her excellent sophomore album that’s earned acclaim from listeners and critics alike. Epiphone now produces a signature model guitar that bears her name, and she’ll have that guitar in tow for this intimate Cactus Club show.

MKE Unplugged: Buffalo Nichols + Stephen Hull @ Jan Serr Studio
Austin-based (and Milwaukee raised) singer and guitarist Carl Nichols—who performs as Buffalo Nichols—returns to town for an unplugged (and free!) performance at Jan Serr Studio on December 9. This performance, which also features local blues guitarist Stephen Hull opening, is the first Buffalo Nichols show in Milwaukee since Fat Possum Records released the project’s astounding and critically-acclaimed debut album earlier this fall.

Sunday, December 12
WMSE’s Big Band Grandstand @ Turner Hall Ballroom
Beloved WMSE DJ Dewey Gill’s annual Big Band Grandstand returns (after a COVID-year off in 2020) to Turner Hall Ballroom! The live event will kick off with Gill welcoming guests with a hand-selected DJ set. The Chicago Jazz Orchestra will take it from there, and the group’s set will include a salute to local jazz legend Woody Herman. And there’s more! A silent online auction will go live two weeks prior to the event. Items will include a Green Bay Packers vs. Minnesota Vikings package, and money raised from the auction will support “the upkeep of WMSE’s studios, and the digitization and streaming of the station’s jazz library, allowing music fans everywhere the ability to hear jazz 24 hours a day, seven days a week.” Fancy dress is encouraged!

Tuesday, December 14
Watkins Family Hour + Courtney Hartman @ Shank Hall
When they’re not winning Grammys, selling millions of records, and cracking the Billboard charts as two-thirds of Nickle Creek, siblings Sara and Sean Watkins are writing, recording, and performing in their aptly-named Watkins Family Hour project, which is finally able to hit the road in belated support of the duo’s excellent 2020 album, Brother Sister, including a December 14 show at Shank Hall that kicks off their abbreviated Midwesten run.

The Lumineers + Cold War Kids @ The Rave/Eagles Club
Exactly one month before releasing their fourth studio album, BRIGHTSIDE, The Lumineers will make their The Rave/Eagles Club debut as part of FM 102/1’s second night of the 2021 Big Snow Show. Cold War Kids will open. Ho! Hey!

Wednesday, December 15
Milwaukee Record presents ‘Clue’ @ Avalon Theater
As this sentence is being written, only 27 tickets remain to this special screening of the 1985 murder-comedy. Hopefully you’re reading this in time to get yours because we will not be adding another showing.

Friday, December 17 and Saturday, December 18
Jackie Kashian @ The Laughing Tap
Since leaving her hometown of South Milwaukee, Jackie Kashian has sustained a long and successful career in comedy that includes a Comedy Central special, a few Conan appearances, and her long-running Dork Forest podcast. She’ll return to the region for two nights of performances at The Laughing Tap in the waning days of autumn.

Friday, December 17 through Sunday, December 19
Donnell Rawlings @ Milwaukee Improv
While there’s a good chance you know him from his work on The Wire or as the guy who said “I’m rich, bee-yaaatch!” (among other memorable roles) as a series regular on Chappelle Show, Donnell Rawlings is also a veteran stand-up comedian. He’ll take the stage in nearby Brookfield for a total of five headlining shows at Milwaukee Improv spread from December 17 through December 19.

Friday, December 31
Horseshoes & Hand Grenades + Buffalo Gospel @ Pabst Theater
Say goodbye to 2021 in style with what’s sure to be a fast-picking, boot-stomping, and rowdy New Year’s Eve performance by two Wisconsin powerhouses. Midwestern bluegrass mainstays Horseshoes & Hand Grenades will be joined by Milwaukee-Nashville country outfit Buffalo Gospel. There’s a lot going on this December 31…especially compared to last year’s final day, but this potent Pabst Theater pairing is definitely worthy of your New Year’s Eve event consideration.

X