In town: Rob Asaro, Doug Benson, Rajiv Satyal, Adam Ray, Darren Knight, Michael Blackson, Claude Stuart, and Joey Folsom.
Leaving a big hole in the list: Dick Gregory was scheduled to be in Chicago next Sunday at the Patio Theater for his show, An Evening with Dick Gregory. Reports say he looked forward to discussing recent events in Charlottesville. He died on Saturday at the age of 84. Dick Gregory’s comedy career began here and he considered Chicago his hometown for many years. He graduated from Southern Illinois University. He served in the military and then took jobs in Chicago at the post office and as a car washer while building his comedy career. One night, Hugh Hefner spotted him and offered him a headlining set at The Playboy Club after another comedian canceled. It was supposed to be a one-time gig. That first night, he endured merciless heckling by a group of racist southern businessmen, but he was such a hit that his run was extended over and over. His success at The Playboy Club led to a profile in Time magazine. Then Jack Paar called, offering Dick Gregory a very coveted spot on The Tonight Show. But no black comedian had ever been invited to take a seat on the couch after a performance. Dick Gregory rejected Jack Paar’s invitations numerous times until producers finally agreed to invite him to sit next to the host. An appearance on The Tonight Show could launch a young comedian’s life into the stratosphere. Career-wise, standing by his principles was a courageous act of death-defying proportions. Dick Gregory would go on to break ground all the way through to this summer as he toured the country in his 80s. In addition to being one of the country’s most influential stand-ups, he risked his life (and comedy career) as a tireless social justice game changer and civil rights activist. He was also a #1 bestselling author, a candidate for Chicago mayor (1967) and for President of the United States (1968), a health and spiritual advisor, and a motivational speaker. He was also a generous mentor to many comedians.
Following is this week’s spotlight. Please confirm all details before heading out!
MONDAY, AUGUST 21
You Listen to White People Music? at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. A solo show by Alison Reese. “Join us as we explore the complex world of a thirteen year old closeted half black girl from Mesa, Arizona through sketch, song, and storytelling.”
Made in America at iO, 1501 N. Kingsbury, 7:00 p.m. A solo show by Rob Asaro who is in from New York. “In 2006 a psychic stopped me on Park Avenue in New York City, spewing out specific and true details of my life. She foretold of an eleven year era marked by double lives, and misplaced ambition. Join me on August 21st and let me regale you with stories of the multiverse, mistaken identity, fantastic disappointment, and untold synchronicities.”
TUESDAY, AUGUST 22
Comedy Cocktail at House of Blues’ Foundation Room, 329 N. Dearborn, 7:30 p.m. and 9:30 p.m. Produced by James Allen Kamp, creator of the most excellent comedyofchicago.com. DJ Tone-Knee kicks off the evening at 6:00 p.m. RSVP for free admission. Early arrival recommended. Seats go fast! Always a great, diverse line-up of Chicago’s top comedians and surprise drop-ins.
7:30: Marvin Phipps, Adam Burke, Ronnie George, Danny Kallas
9:30: Marvin Phipps, Harold Pierre, Chris Trani, Adam Burke
Extraordinary Stan Lee Livestream at The Music Box Theatre, 3733 N. Southport, 8:00 p.m. This supersized celebrity tribute to Stan Lee is hosted by Chris Hardwick and will be livestreamed from L.A.’s Saban Theatre.
Fantastic Super Great Nation Numero Uno at Second City, 1616 N. Wells, 8:00 p.m. The e.t.c.’s 41st revue. “ … as divided as the nation may be, there is still hilarity in our humanity.”
Winner … of Our Discontent at Second City, 1616 N. Wells, 8:00 p.m. The 105th Mainstage revue. Tickets sell out fast. Check site for additional shows throughout the week.
Larry Reeb at Zanies, 1548 N. Wells, 8:30 p.m. This Chicago icon is at Zanies downtown through Sunday to impart some advice from your Uncle Lar. Follow link for all show times.
Chicago Underground Comedy at Beat Kitchen, 2100 W. Belmont, 9:30 p.m. Chicago Underground Comedy is one of comedy’s most groundbreaking showcases where Cameron Esposito, Beth Stelling, TJ Miller, Dan Telfer, Kumail Nanjiani, just to name a few, got their start. Produced by Meredith Kachel.
Ride Share Ensemble Show at The Comedy Bar, 500 N. LaSalle, 9:30 p.m. The wildest Uber stories! Free show featuring Comedy Bar interns with headliners Carly Kane and Mickey Housley.
WEDNESDAY, AUGUST 23
Doug Loves Movies at Thalia Hall, 1807 S. Allport, 8:00 p.m. Doug Benson is in town to record his podcast with a surprise guest.
Adam Ray at Zanies, MB Financial Park, Rosemont, 8:00 p.m. Through Saturday. Follow link for all show times.
Comedians You Should Know at Timothy O’Toole’s, 622 N. Fairbanks Ct., 9:30 p.m. Marty DeRosa hosts Blake Burkhart, Brandi Denise, Ricky Gonzalez, Joe Kwaczala and Matt Riggs.
THURSDAY, AUGUST 24
Southern Momma and Em Tour at The Improv, Woodfield Mall, Schaumburg, 7:30 p.m. Darren Knight brings social media star Southern Momma to Schaumburg for one night only.
The Price is Wrong, Bitch! at Stage 773, 1225 W. Belmont, 7:30 p.m. The Chicago Red Line presents contemporary comedic cabaret in a game show format. Thursday and Friday night and Sunday for a mimosa brunch. Follow link for all times and details.
Rajiv Satyal at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. In tonight’s show, “Taking a Stand,” Rajiv Satyal explains how pop music got this country where it is. With singer/songwriter. Taylor Alexander.
Seven Sisters Comedy Variety Hour at Second City, 1616 N. Wells, 8:30 p.m. The Seven Sisters are Allie Keller, Phylicia McLeod, Meghan Murphy, Emily Batek, Cassie Belek, Jodie Meis, and Katelyn Woolcott.
Claude Stuart at Zanies, 4051 E. Main St., St. Charles, 8:00 p.m. Through Saturday. Follow link for all show times. Claude Stewart is known as “the world’s first physical insult comedian.”
Group Improvised Comedy at Comedy Clubhouse, 1462 N. Ashland, 8:00 p.m. Long form improv (20-25 minutes) by three teams of up to 10 improvisers, each based on an audience suggestion. Thursdays through Sundays. Follow link for details, show times and a great explanation of what makes improv an art form like no other.
Lenny Bruce is Back at Second City, 1616 N. Wells, 10:30 p.m. Starring stage and film actor Joey Folsom, this show is stopping in only a few select cities. Lenny Bruce was one of the most influential stand-up comedians and social critics in American comedy history. Never afraid to state the truth as he saw it, he was free with his language and didn’t care about the social “norms” of the times. He was arrested multiple times on obscenity charges, convicted in 1964, and pardoned only posthumously. In a 2006 Chicago Sun-Times interview, Dick Gregory was asked to name his comedy idols. He said, “This culture produced three comedic geniuses — Mark Twain, Lenny Bruce and Richard Pryor.” Friday and Saturday nights at 7:30 p.m.
Messing with a Friend at The Annoyance Theatre, 851 W. Belmont, 10:30 p.m. This is a show where the improvisers morph from character to character before your eyes. Believable and magical at the same time. A little bit dangerous, too. Anything can happen. Susan Messing was named “Best Improviser” by the Reader and “Improviser of the Year” at the Chicago Improv Festival. This week’s friend is Andel Sudik. (yesandel.com.)
FRIDAY, AUGUST 25
Drinkers with Writer Problems Presents: Lit Up! at Brisku’s Bistro, 4100 N. Kedzie, 7:30 p.m. Live lit, including including short stories, first person essays, humor, poetry, and creative nonfiction. Tonight: Beth Dugan, Harold Holt, Pari Karim, Andy Karol, Aaron Cynic, Elizabeth Gomez, and Anita M. Mechler. Hosted by Jeff Phillips.
Comedy Cruise with Zanies at Navy Pier Polk Bros’ Park, 8:00 p.m. Hosted by Kelsie Huff. Featuring Jim Flannigan. Headliner: Pat McGann.
A sample of Kelsie Huff’s beautiful, contagious energy:
Rajiv Satyal at The Skokie Theatre, 7924 Lincoln Ave., Skokie, 8:00 p.m. In tonight’s show, “Taking a Stand,” Rajiv Satyal explains how pop music got this country where it is. With singer/songwriter. Taylor Alexander. Plus: Azhar Usman is opening!
Michael Blackson at The Improv, Woodfield Mall, Schaumburg, 7:30 p.m. and 9:45 p.m. Friday and Saturday nights. Follow link for all show times.
Told at iO, 1501 N. Kingsbury, 8:30 p.m. Special guest: Rick Bayless. Improv inspired by stories, music, and truth-telling.
SATURDAY, AUGUST 26
ComedySportz at CSz Theater, 929 W. Belmont, 6:00 p.m., 8:00 p.m., 10:00 p.m. Ninety minutes of heart-pounding and hilarious short-form improv games inspired by audience suggestions. All ages are welcome!
Two Hour Comedy Hour at Gallery Cabaret, 2020 N. Oakley, 7:00 p.m. Free stand-up showcase. Always a great line-up.
Mainstage Showcase at The Comedy Clubhouse, 1462 N. Ashland, 8:00 p.m. Featuring the women of One Group Mind.
Fuck Trump: A Collection of Songs to Demonstrate What a Horrible Person Donald Trump Is at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. Directed by Mick Napier, the world renowned founder and director of The Annoyance.
SUNDAY, AUGUST 27
Comedy at Wrigley Field, 12:00 p.m. An afternoon of free comedy from Storytown, ComedySportz and The Laugh Factory. Follow link for details.
Hoo Ha Comedy: Summer Bash at Schuba’s Tavern Upstairs Lounge, 3159 N. Southport, 8:30 p.m. Tonight: Lainie Lenertz, Krisin Fenchak, Audrey Jonas and Megan Stalter. Featuring Tim McLaughlin, Michael Regan and Marilee.
You can stay up to date with Comedians Defying Gravity by typing your email address in the box and clicking the “create subscription” button. My list is completely spam, spam, spam, spam free, and you can opt out at any time.