Originating long before the city had anything even resembling a sustainable comedy community, Milwaukee Comedy Festival has grown and evolved in kind with Milwaukee’s humor scene. In fact, the annual comedic undertaking has been an invaluable means of pushing local comedy to exciting, new territory. Starting unofficially with tonight’s Roast Of Milwaukee and with tomorrow’s Voyager show at Landmark Lanes before formally running from July 31 to August 4, the Milwaukee-curated undertaking will once again serve up and eclectic array of laughs in its 14th year.

Though Milwaukee Comedy Festival has essentially already guaranteed this year’s installment will be its biggest and best one yet by announcing headliners like Todd Barry, Ari Shaffir, Beth Stelling, and Judah Friedlander, there’s a lot to be excited about over the course of the 18 events taking place at nine venues over the course of seven days. You can get single-day tickets, ticket four-packs, giggle show packs, and all-access passes HERE. We’ll see you there, Milwaukee!

Monday, July 29

Milwaukee Record’s 5th annual Roast Of Milwaukee @ Club Garibaldi
Back in 2015, we decided to help informally kick off the Milwaukee Comedy Festival by asking comedians to gently (or, in some cases, straight-up viciously) make fun of the city they love in our inaugural Roast Of Milwaukee event. Following the wonderful response to those verbal punches thrown in the direction of Milwaukee, we decided to do it again with an even bigger and better event at Club Garibaldi in 2016. Then we did there again in 2017 and 2018—which featured memorable sets from media personalities like Ted Perry, Ramie Makhlouf, Tarik Moody, and Jon Adler along the way.

Since there’s no shortage of great material about Milwaukee out there, we figured we’d do it again. Join us at Club Garibaldi on Monday, July 29 for our 5th annual Roast Of Milwaukee. In addition to the outstanding cast of local stand-ups taking the stage, 88Nine’s Dori Zori will also serve as the event’s emcee. The host will be joined by Eric Smith, Raegan Niemela, Elijah Holbrook, Drew Flagge, Mike Korbin, Gary Zajackowski, Amy Westrup, Jeff Spankowski, and maybe even a surprise guest or two. Get your tickets while they last.

Tuesday, July 30

Voyager @ Landmark Lanes
The popular monthly showcase will offer a special edition “pre-kick off” show to prepare people for the Milwaukee Comedy Festival. As always, the FREE showcase at Landmark Lanes features four comedians booked to perform eight-minute sets. As usual, there will also be two comics drawn for random five-minute “bucket spots,” so if you’re salty about not getting accepted to the festival proper, here’s your shot to be a part of it. Or you can just come and watch a free preview of what’s coming the rest of the week.

Wednesday, July 31

Keg Stand Up @ Lakefront Brewery
Though Milwaukee Comedy Festival only comes but once a year, Milwaukee Comedy’s great Keg Stand Up showcase is a year-round fixture that always brings the best regional comics to Lakefront Brewery Beer Hall stage and never disappoints. This month’s headliner is Denver comedian Sam Tallent, who will be joined on the fest’s first official show by the likes of Rachel Manson, Darius Kennedy, and Riley McCarthy.

Thursday, August 1

Todd Barry @ Shank Hall
Fresh off releasing his outstanding Netflix special, Spicy Honey, in 2017 and a pair of sold-out shows at Milwaukee’s Underground Collaborative last year, veteran comic Toddy Barry will head up an Shank Hall show on Thursday, August 1. He’ll be joined on this stacked Thursday night showcase by some awesome local talent in the form of Dana Ehrmann and Mike Berg.

Other shows:
10 p.m. @ The Vanguard with Dana Ehrmann, Riley McCarthy, Bill Gevirtz, and Piers Moreton

Friday, August 2

Judah Friedlander @ Shank Hall
Actor, author, comedian, music video hug-giver, and trucker hat proponent Judah Friedlander will also be keeping the comedy rolling into the weekend. Fresh off the release of last year’s acclaimed Netflix special, America Is The Greatest Country In The United States, the former 30 Rock series regular will be performing all new material at Shank Hall on Friday, August 2 as part of his “Future President” tour. Local treasure and noted battle rapper Carter Deems opens.

Other Shows
10 p.m. @ The Underground Collaborative with Samantha Berkman, Drew Flagge, Mike Jonjak, and AJ Grill

Midnight @ The High Note
Comedy Festival showcase and karaoke

Saturday, August 3

Beth Stelling @ Shank Hall
The hilarious and all-around wonderful Beth Stelling has been a fixture on late night shows. She’s had specials on Netflix and Comedy Central, and her “We Called Your Mom” podcast is as innovative as it is delightful. The Ohio native will make her Midwest return to head up a show that could quietly go down as the best show of the entire festival. Prateek Srivastava will open.

Other shows:
11 a.m. @ Var Gallery & Studios with Mike Hover, AJ Grill, and Tooky Kavanagh

3 p.m. @ The Underground Collaborative with Daryll Schmitz, Tooky Kavanagh, MK Paulsen, and Mike Hover

5 p.m. @ The Underground Collaborative with Vanessa Tortalano, Garden Boys, and Andy & Alosha

10 p.m. @ The Underground Collaborative with Craig Smith, Raegan Niemela, Ramie Makhlouf, and Lisa Curry

Midnight @ The Underground Collaborative with Cameron Little, Bobby Hill, and Lam Guluka

Sunday, August 4

Ari Shaffir @ Turner Hall
Seminal stand-up and This Is Not Happening host Ari Shaffir will bring Milwaukee Comedy Festival to what’s sure to be a thrilling and memorable conclusion with a headlining performance of his new hour, which is entitled “Ari Shaffir: Jew” at Turner Hall on Sunday, August 4. Openers have not been announced, but you’re sure to be in for a treat.

Other shows:
11 a.m. @ Pabst Milwaukee Brewery & Taproom with Marne Litfin, Tok Moffat, and Tyler Menz

3 p.m. @ The Underground Collaborative with Tok Moffat, Marne Litfin, Jamal Russell, and Ryan Mason

5 p.m. @ The Underground Collaborative with Sabeen Sadiq, Eric Smith, Piers Moreton, and Adam Yenser

About The Author

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Co-Founder and Editor

Before co-founding Milwaukee Record, Tyler Maas wrote for virtually every Milwaukee publication (except Wassup! Magazine). He lives in Bay View and enjoys both stuff and things.