Lewis Black, Nick Offerman and the Best St. Louis Comedy Shows in May 2015

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Kyle Kinane will perform at The Ready Room on May 21 - MOSES ROBINSON // COMEDY CENTRAL PRESS
  • Moses Robinson // Comedy Central Press
  • Kyle Kinane will perform at The Ready Room on May 21

"Best" is a relative idea, much like what any individual person finds funny. That's why each month we recommend various comedy events -- some sketch, some improv, some standup and some a little of everything -- and deem them the best. If you're in search of a laugh or willing to take a risk on humor, read on for the comedy shows coming to St. Louis this month that caught our eye. Whether you want to see tried-and-true veterans or the green open mic-ers, May has it all.

First, hats off to the Peabody Opera House for stacking the first weekend in May with a pair of powerhouse acts. Saturday, May 9 Lewis Black is back in town with his new show The Rant is Due, Part Deux. And the following night, Sunday, May 10, Megan Mullally and Nick Offerman take to the very same stage with their show "Summer of 69: No Apostrophe." Neither show is for the faint of heart; blushing beauties are best suited to stay home.

Other highlights this month follow....

COMEDIENNE: Todd Masterson Saturday, May 16 at Cicero's $12 | 9 p.m.

Todd Masterson wants to make strangers and friends alike laugh until it splits their sides. He's a towering man whose smile could light the darkest room. He also wants to be huge on Twitter. His sense of humor is playful, honest and unwavering. While his may not be a household name, Masterson's wit has landed him writing gigs with a few whose names are, including Joan Rivers and James Franco.

Todd's live show, "COMEDIENNE," features Benton Greyson and will be hosted by No Straight White Guys, Milly Naeger. It's been too long since Cicero's has hosted a comedy show; it's a great shotgun room with a low stage. It was the very place where Punch Drunk Comedy, now Bare Knuckle Comedy, cut their chops and kick-started the alt comedy scene.

Kyle Kinane Thursday, May 21 at The Ready Room $15 - $18 | 8 p.m.

Right about a year ago Kyle Kinane (with the help of Dave Ross) sold out The Firebird. Lucky for us, he's coming back for Round 4 in the Lou on his way west to headline Crom Comedy Festival in Omaha. If you're unaware of the tragically hilarious stylings of Kyle Kinane, this is what you ought to know: He embodies the kind of transparency most comedians spend years working towards and never fully achieve. At 39, Kinane's latest album, I Like His Old Stuff Better, is a handful of coming-of-age tales from the perspective of a (formerly) bearded, charmingly belligerent and relentlessly self-aware individual.

It's been said that laughter originated as a sign of safety before the development of language. One cave man warns another of a saber-tooth tiger on the horizon when alas, it's just a shadow on rock. To express the passing tension, our cave man enthusiastically exhales (laughs) to signal there is no danger to fear. That's the fundamental dynamic of Kinane's humor. He takes you down a road you're not sure you want to go, and at that moment when things could go from bad from worse, he reassures they can and will. But then, in his own special way, Kinane reminds you it's all happening to him, not you -- and oh the relief, joy and laughter.

Turn the page for more great May shows.

STUPID BRAIN
  • Stupid Brain

Stupid Brain Wednesday, May 27 at The Improv Shop $5 | 8 p.m.

A duo whose manic energy is a force to be reckoned with, Bobby Jaycox and Steve Raines are the life of the party. Now they're back at it again and throwing one of own at The Improv Shop. Their irreverent love child, Stupid Brain, is back for its third and much anticipated installment. Together they fuse together elements of improv and standup to create a show that's seductively unpredictable.

The best thing about combing improv and standup is it's not strictly a sitting and listening experience; audience participation is (at times) required. Plus there's just no telling what Raines and Jaycox have up their sleeves. During the intermission of the inaugural show you could pay $1 to slap either host in the face.

As for the lineup; Jeremy Essig and Patrick Moore will be taking care of the standup side, while Boothby and Meowsers tend to the improv. It may be the most fun you could possibly have at a show.

Picnic Time with Julia Prescott Friday, May 29 at Art Bar No Cover | 9 p.m.

Bar shows are tough. The regulars and the unsuspecting people just trying to enjoy a drink have to be convinced what's happening on stage is more worthy of their attention than the whiskey in front of them or the friend beside them. The comics have to worry about who's coming through the doors next, or who's had just the right amount of tequila, making focusing on their jokes a daunting task. Distraction can be (and often is) the death of standup. If only there was a back room where the show could go on uninterrupted...

Enter Art Bar, a thriving watering hole in the heart of Cherokee with a small studio space and, yes, a door to keep the comedy in and the unruly out! Quartered off, safely away from the unsuspecting drinkers, Justin Luke and Ben Johnson have transformed Art Bar's studio into a comedy clubhouse once a month for their show Picnic Time. They're just two months in and already bringing in top acts.

Making her way in from LA, VICE writer Julia Prescott will be headlining May's show. She'll be sharing the corner of the room with locals Ryan Dalton, Sarah Bursich, Ella Fritts and Matt Rose. Julia is one of those up-and-coming comedians whose writing credits boast names and shows more familiar than her own -- but she's definitely on her way. See her now for free while you still can.

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