Image via YouTube
“My benefits at work are pretty sick, so I’d be a fool to give up all of that.”
That’s not the only reason Milwaukee comedian Drew Flagge remains bi-vocational. His blue-collar day job provides unending inspiration for what occupies his night shifts.
As for the occupation with the awesome benefits package that provides so much of his comedic fodder, Flagge offers, “I can’t say where it is, but I’m in and out of grocery stores every day. So, I just observe people living their lives, and a lot of times people just say things to other people that make me wonder why people act the way they do. People are just all weird, and this last year really exposed it.” For example, “I think we all turn down the radio in our cars to parallel park, but now we pull down our masks to hear each other. Stuff like that makes me laugh.”
Flagge intends to make others laugh at what he finds funny when he joins fellow local stand-ups Dana Ehrmann, Eric Smith, J. Tyler Menz and David Louis amid the artworks at Var Gallery & Studios (643 S. 2nd St.) at 8 p.m. Friday, June 11 for the return of “Subjective: A Comedic Showing.” The monthly event curated by Milwaukee Comedy's Kaitlin McCarthy emphasizes the aesthetic quality of comedy, requiring its participants to articulate an artist statement and take questions and critiques from audience members. Flagge has met those challenges in the past and is up for them again.
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“I’ve done this show before, so writing an artist statement isn’t anything new. Plus, we do have an open mic in that venue, so I’m really comfortable writing about how I feel about my comedy. And really all I can do is answer the questions honestly,” he says of his readiness to again be put on display amid Var’s other exhibitions. But Flagge doesn’t venerate his specialty above any other when it comes to viewing comedy as art. “I definitely consider it an art, but so is cooking. Anyone can cook but it comes down to how hard are you willing to work at it to stand out.”
Comedic Success
And just as anyone can pick up what it takes to make a great meal from one of the supermarkets he visits in his other profession, Flagge notes that everyone possesses at least the building blocks of comedic success. “We all have the basic ingredients to make comedy,” he insists. “Everyone is funny with their own group of friends. The thing that makes it an artform is being able to take all of those ingredients your friends or family enjoy about you and making it relatable, or for lack of a better term, marketable, for complete strangers.”
Flagge’s path to becoming marketably amusing didn’t start with any grand epiphanies. “There’s really no special origin story to it, I used to watch Comedy Central’s Friday night half-hour specials and thought it’d be cool to do comedy.”
Five tries at the open mic hosted by the old Comedy Cafe on Brady Street and encouragement from fellow Milwaukee funnyman Jairite Robinson helped push him to being the comedy multi-tiered presence now.
Double-Trebled Comedy
Apart from performing his own shows, Flagge hosts The Double-Trebled Comedy Open Mic, 8 p.m. Tuesdays at The High Note Karaoke Lounge (645 N. James Lovell St.). That gig birthed the podcast Guys Being Dudes with Ryan and Drew wherein he and co-host Ryan Graham “hang out at the High Note, and we just riff with other comics that were at the mic and try to make jokes about whatever’s in the news or sports or movies.” Flagge's followers will for now have to wait for new episodes because “we were getting really burnt out staying out until midnight on weeknights.”
And though opportunities like “Subjective” may offer means for Flagge to take his comedy further, he seems content with where he is now. “More than likely comedy will never be my full-time career. I’m awful at promoting myself. I’d love to go do more cities and visit other scenes outside of Milwaukee, Madison, and Appleton, but right now, financially, I’m not close to stable enough to do that.”
Flagge is funny enough to have a comedy career so prosperous to keep him from hanging onto his current benefits package, but in the meanwhile, his recommendation to attend “Subjective” is certainly stable. “The show is fun, the lineup is good, there’s a little something for everyone on this show so it’ll be a good time.”
Here Flagge is in his zone from a couple years ago:
