From Pee-wee Herman to Gabriel Iglesias, These Are the Best Comedy Shows in Chicago This March

Wednesday, March 4, 2020
From Gabriel Iglesias to a celebration of Pee-wee's Big Adventure, these are this month's must-see comedy shows and events coming up in Chicago.
Bobcat Goldthwait at the Den Theatre Perhaps one of the most recognizable comedians working today, Goldthwait’s career has spanned more than 30 years in show business and has found him wearing a number of different hats, including director, actor, voice actor, and screenwriter. His current live show and stage presence is a far cry from what he was known for in the ’80s (the guy with the zany voice), and his act now centers around his personal life, politics, and hilarious stories from the road. Local comic Matty Ryan is opening. Details: March 6 and 7, 7:30 p.m. and 9:30 p.m.; $22
Photo courtesy of Andrew Santino/Facebook
BUTT at the Hideout Sketch group founders and former Chicago residents Joe McAdam and Chris Stephens return from their Los Angeles base for an evening of fresh material and general absurdity. The two have been slowly building a cult following, having performed sketches for Comedy Central, IFC, and Funny or Die, and are likely to “blow up” very soon. L.A. comedians Sam Wiles and Brendan McGowan (also formerly of Chicago) open the show. Details: March 11, 9 p.m.; $10 Andrew Santino at Thalia Hall Comedian and host of the podcast Whiskey Ginger, Santino returns to his native Chicago, his last appearance being at the Vic in 2017 for his Showtime taping of ​Home Field Advantage.​ He is also known for playing the lead in the ABC show ​Mixology​ and NBC’s This Is Us​, as well as Showtime’s ​I’m Dying Up Here​. Later this year he’ll be starring in an FX show alongside Lil’ Dicky. Details: March 13, 6:30 p.m.; $35–$45
Photo courtesy of Gabriel Iglesias/Facebook
Gabriel Iglesias: Beyond the Fluffy World Tour at the United Center Currently one of the biggest comedians in the world, Gabriel “Fluffy” Iglesias is on a world tour, selling out stadiums and arenas around the globe. In the past, he’s sold out the Staples Center, Madison Square Garden, and the Sydney Opera House, a feat that very few comedians have accomplished. Over the past 20 years, he’s garnered a slew of stand-up specials and TV/movie credits, his most recent being the Netflix original series ​Mr. Iglesias,​ wherein Iglesias plays a teacher at a high school in Long Beach, California. Details: March 14, 8 p.m.; $49
Photo courtesy of Lewis Black/Facebook
Lewis Black: It Gets Better Every Day Tour at Belushi Performance Hall Having just stopped through Waukegan and Elgin within the last month, the king of the rant, Lewis Black, is making an unprecedented third suburban stop for those who live in the comfortably far reaches of Chicago. Black’s long and illustrious career has included countless TV appearances, Broadway, several books, and hour-long specials. He’s a playwright, a critic, an actor, and, most important, a stand-up comedian and household name. Details: March 14, 8 p.m.; $65 Pee-wee’s Big Adventure 35th Anniversary With Paul Reubens at the Chicago Theatre The iconic movie turns 35 this year, and if that makes you feel old, well, you kind of are. And that’s OK! Relive the ridiculous antics and magic of one of the most beloved characters of the ’80s and ’90s, Pee-wee Herman. The evening will feature a screening of the film, followed by stories about the making of the movie. Details: March 19 and 20, 7:30 p.m.; $39–$75 Nikki Glaser: Bang It Out Tour at the Vic Theatre With more than a decade under her belt, Glaser’s career continues to get hotter. She has had multiple stand-up specials and TV appearances, as well as hosted two shows for MTV and another for Comedy Central, and most recently put out an hour special for Netflix. She currently hosts a daily morning radio show called You Up With Nikki Glaser on the Comedy Central channel of SiriusXM. Details: March 21, 7 p.m. and 9:30 p.m.; $35 Do You Believe in Madness? Second City’s 108th revue finds an almost entirely new main-stage cast, a couple of whom made the jump from the e.t.c. stage. ​Do You Believe in Madness?​ follows the essential SC format with a mix of political and pop culture sketches, improvised scenes, and musical numbers. This iteration promises to “hilariously examine how we’re all gleefully speeding toward a modern apocalypse,” including breaking down Brexit, infiltrating Facebook, and legalizing weed. Details: Open run at Second City’s main stage; showtimes and prices vary