Online comedy calendar for Chicago & beyond: Inauguration Day through Thursday, January 28, 2021

Chicago comedians in the news: Mike Lebovitz proves that the year is just getting better with his new album Two Slob Household. Mike is one of the founders of “Comedians You Should Know,” a nationally known showcase based in Chicago, and appeared on Last Comic Standing, Comedy Central and HBO’s The Deuce. Find Mike’s album at Stand Up! Records.

On January 19, Kumail Nanjiani opened the AAPI Inaugural Ball to celebrate the inauguration of Joe Biden and Kamala Harris. You can read more about it here.

Following is a sample of online comedy over the next week. Please confirm all details and especially time zones!


Whisky and a Cookie Inaugural Ball 7:00 p.m. With Patti Vasquez.

The 1/20 420 Comedy Extravaganja Inauguration Special 8:00 p.m. With Cooking on High’s Ngaio Bealum and also featuring Margaret Cho, Daniel Rugg Webb, Atsuko Okatsuka, Ta’Vi, and Drea Myers.



Vail Comedy Show 6:30 p.m. Pre show begins 30 minutes early. With Dave Waite (Jimmy Fallon, Comedy Central, Last Comic Standing), Leah Bonnema (Late Night with Stephen Colbert, truTV, IFC, VH1), Casey Crawford (Jimmy Kimmel), Sofiya Alexandra (Comedy Central, Second City), Long John The Comedian (Comedy Test Kitchen, 2020 Outstanding Comic of the Year, 2019 Steve Harvey award winner), Chris D. (Rob Gronkowski’s Unsportsmanlike Comedy). Hosted by Mark Masters.

Judy Gold 8:00 p.m. With Tony Devo. Followed by a VIP Meet & Greet.

Craig Robinson 9:00 p.m. With Chicagoan Craig Robinson. Featuring Rainer Pollard, Katie Cazorla, Matt Rife, and Ruben Paul live from the Laugh Factory in Hollywood.


Laugh Out Loud Improv 8:00 p.m. From the improv theater in Chicago and Schaumburg. Tonight and Saturday.

Judah Friedlander 8:00 p.m. Featuring Joyelle Johnson. Hosted by Jen Saunderson. Livestream standup and crowd work.

SheRocks Awards 8:30 p.m. Margaret Cho is among the honorees who include Nancy Wilson, Amy Lee, The Go-Gos, Cindy Blackman Santana and more. Pre-show at 8:00 p.m.

Crazy Funny Asians 10:00 p.m. Comedians include Chicago’s Prateek Srivastava.



Second City Really Awesome Improv Show 3:00 p.m. Family-friendly.

Funny Women of a Certain Age 7:00 p.m. Featuring Vanessa Hollingshead, Leighann Lord and Julia Scotti. Hosted by Carole Montgomery. Followed by a VIP Meet & Greet.

Zanies 8:00 p.m. LAUGH MORE LIVE! Calvin Evans hosts Erica Nicole Clark, Joey Villagomez, Jim Flannigan, and Dario Durham. Live from Zanies in Rosemont.

Therapy Players 8:00 p.m. Post-Inauguration Show and free healthcare! The Therapy Players are Chicago’s award-winning and only all-therapist improv group!

Laugh Factory 9:00 p.m. Adam Ray, Doug Benson, Jackie Fabulous, Pablo Francisco, Jonathan kite, Nick Guerra. Live from the Laugh Factory in Hollywood.

Black Laughs Matter 10:00 p.m. Hosted by originally Chicago comedian Terry Dorsey.


How to Win Live Comedy Competitions 7:30 p.m. With Paul Conyers. A KO Comedy production by Sammy Obeid.


Monday Night Funnies 7:00 p.m. Denise “Comic Blonde” Medina and Mark Klaber produce this memorable show twice a month. Always a diverse, hilarious lineup and an oasis of laughter. Host Jessica Winther keeps it flying with her impossibly fast mind and inventive riffing. No two shows are the same! Anything can happen and it does. Not to be missed. Free, but donations appreciated – this week, please consider giving directly to the Lupus Foundation of America.


Dave Barry 7:00 a.m. “A Breakfast with Hope.” Dave Barry discusses his book Lessons From Lucy. Sponsored by Sylvester Cancer Center.

Todd Barry 7:00 p.m. The Virtual Crowd Work Tour.


Uncle Clyde’s Comedy Contest 9:00 p.m. Live from Flappers Comedy Club in Burbank, CA.


Bob Saget 6:00 p.m. “The Upside of Walking Through Hell.” Sponsored by the Emanu-El Streicker Center. With Rabbi Steve Leder.

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.


Leave a Reply