Upstairs Gallery Chicago

You like Art? You like Performance? SO DO WE
Located in the thick of Andersonville, The Upstairs Gallery is a spot for creative endeavors of all kind!

Feel free to reach out for more information:

5219 N. Clark Street, Chicago, IL 60640

Upstairs Gallery Bulletin #68 (8/3-8/19) “WELCOME BACK CAIT AND WALT”

After a hectic week without Walt and Caitlin Alex is very very glad to HAVE THEM BACK. Now all those lovable gallery hiccups will be smoothed over as the well oiled MACHINE that is the upstairs gallery is back up to full operationnnnnnnn. For real though, thanks to all the folks who helped Alex keep it together last week! Ya’ll are Angels for real! More workshop announcements! More fun! MORE THIS WEEK AT THE GALLERY

-WORKSHOPS- We’ve started a mailing list! Sign up HERE

  1. Kevin Mullaney Fall Performance Class - 8 Classes, 4 performances - $199 - An eight week class for intermediate and advanced improv students with some long form improv experience.  The class includes four performances at Upstairs Gallery in Andersonville. Each show will be hosted by your teacher and you will receive notes after the show. The following week, in class, will feature exercises to work on the specific areas of potential improvement identified from the last show. Students can apply to be in this class by filling out this form before midnight on Monday August 20th. More info here.
  2. Boot Camp” with Holly Laurent & Greg Hess September 9, 1-5pm $60  Want a workshop where you get notes just for you? Holly and Greg will focus on you the performer, how to create better scenes, and expand your potential as an actor and improviser. This class is designed for personal feedback and numbers are limited.  Please note the longer class length — we plan to use all of it! Holly is a member of the Second City Mainstage and The Reckoning. Greg is a member of Cook Co. Social Club and Improvised Shakespeare. Both have taught at iO Chicago and Second City, among others. To sign up, please email

Dropped. We’re way proud of it. Check it out!

Mitch Greene Presents: Monkeyshines 

Monday- August 6, 13, 20, 27 - 8:00pm Free! (Donations Accepted) BYOB

A wonderfully strange variety show featuring various acts such as sketch, music, improv, dog acts, jugglers, monologues, a mime, and more. 

Different each week. (Velvet Rope set tonight!)

Hosted by Mitch Greene, with special appearance by Rick California! 

Produced by Jay Austin Sukow

(Facebook Event)

The Pocket War! Unclassified- Upstairs Gallery run!

Tuesday -August 7, 14, 21, 28 - 8:00pm Free! (Donations Accepted) BYOB

Pocketful of Posers and The War Room presents, The Pocket War! Unclassified Improv Comedy Show case!

  • Pocketful of Posers ARE Alex Leong, Michael Johnson, Chris Fair, Megan Renner and Andrew J. Daniels
  • The War Room ARE Brandon Reich, Steph Jacobson, Chris Fair, Melina Barona and Stu Allard

We have fun, Special guests too!!!

August 14th- (Chris Fair’s Birthday Show) - (There will be Cake!!!)

  • The Laser Improv Show. 
  • The Adventurers 
  • Old Smuggler 

(Facebook Event)

Making Out with Wes Perry and Friends - AUGUST

Wednesday - August 15th - 8pm, Free (Donations Accepted) BYOB 

A low-key evening of comedy, music, and heavy-petting. IF WE TOOK A HOLIDAY - A SPECIAL VACATION EDITION. This month Wes will be telling stories and singing songs about vacations gone awry, including his recent trip to sunny San Diego.

Musical accompaniment by guitarist Adam Cohen-Leadholm and drummer Ross Howard.


  • Jeff Murdoch - An improviser from iO Chicago
  • Trandroid - A gender ambivalent robot, queer performer extraordinaire, and the hostess of Nuts and Bots, and Shits and Giggles
  • Joey Dundale - A comedian, writer, and host of KILL ALL COMEDY at the Upstairs Gallery
  • Matt Leyes - A visual artist, beauty expert, and storyteller
  • Morgan Lord - An improviser and the host of The Sweater Kittens Variety Show at Cole’s Bar
  • Mark Logsdon - An improviser from iO Chicago and the Annoyance 
  • Shaun Sperling - A Moth StorySLAM winner, who will be debuting a new work called “Madonna and Me”

(Facebook Event)

Adam Cole’s “Frankenstein”

Thursday- August 2, 9, 16, 23, 30 - 8pm, Free (Donations Accepted) BYOB

A different solo show every week! Adam brings in the dead body of a show - the audience’s suggestions give it life - at the end of the night we chase the show through Andersonville, and try to rescue the woman (Walt Delaney) it has captured.


  • aug 16 - Hunks ‘R Us

Part of a two month solo show extravaganza (Gary Richardson hits the stage thursdays in September)

(Facebook Event

Dead$$$ celebrates americana all summer 

Thursday August 9, 16, 23, 30 - 10:30pm, Free (Donations Accepted) BYOB

you probably spend your time sitting around wondering what an improv team made up of mike brunlieb, dara katz, matt barats, steph cook, and vince portacci looks like, don’t you?

well stop wondering and START LIVING.

every thursday in july/august, dead$$$ shows you how to LIVE.

This week Feldmanowski and Hunkz R Us open!

(Facebook Event)

All of Our Feelings at Once: Variety and Miscellany 

Friday- August 17th- 8pm, Free (Donations Accepted) BYOB

Here’s the thing: Alison Lynch, Britta Rowings, Jesse Thurston, and Rebecca Loeser have done it again! Join us once more at the Upstairs Gallery for a beautiful night of variety, miscellany, and Fla-Vor-Ice.

You’ll laugh, you’ll cry, and you’ll eat Fla-Vor-Ice. It feels off balance if I don’t mention it one more time, so Fla-Vor-Ice.

(Facebook Event)

Spend Some Time with Jamison Webb

Saturday- August 17th- 10:30pm, Free (Donations Accepted) BYOB

Physical challenges with a very low risk of injury, surprise guests that aren’t really that surprising because they’re drawn from my circle of friends, and life-affirming miracles.

Not a talk show. Not a one-man show. I don’t know what this will be, and you don’t either.

(Facebook Event)

Ladies Love Upstairs Gallery: August Fun Timez!

Saturday- August 18th- 8pm, 
Free (Donations Accepted) BYOB

Happy August, everyone! Can you believe it’s here already? I can hear the cicadas calling me back to field hockey pre-season and the hot, sticky weather telling me to go load up on notebooks and pencils (with matching pencil cases, natch.) Good news, though! As well adjusted, extremely mature adults, August now means a fresh new show in the Ladies Love Upstairs Gallery series!!! Sadly, the original Ladies Love hostess with the mostess, Devin Bockrath will be off dazzling the world with her wit and charm (again! Be less cool, Devin! We miss you!). But have no fear! The ever marvelous Sarah Shockey is here to bring her world class, razzle dazzle to host the evening. Get ready for some fuuunnnnnn! 

Featuring the talents of:

  • ’92 Dream Team – Becca Taubel, Laura Bloechel, Jen Francis, Erin Morrill, Ashley England, Emma Pope, Claire Mullaney
  • The Slut and the Maven – Brigid Marshall, Carly Mandell
  • Birds – Maria Randazzo, Blair Beeken, Lilly Sullivan
  • Desi Arnaz – Claudia Martinez, Morgan Lord, Becca Taubel, Blair Beeken

(Facebook Event)


Saturday August 4, 11, 18, 25 - 10:30pm - Free (Donations Accepted) BYOB
Hot comedy time from two gallery proprietors and their friend Brian in the form of a 3 man improv EXPLOSION. DROP BY FOR THE FUN.

  • 8/18 - Caitlin Barlow is hosting a book drive at the gallery ALL MONTH LONG. on this night we’ll be joined by the Katydids to make a big push! BRING YOUR BOOKS!

(Facebook Event)


Sunday - August 5, 12, 19, 26 - 8pm Free! (Donations Accepted) BYOB

JoeZoShow presents JoeZo”Doc”Show. An evening of sketch comedy, or it was, until legendary documentary film maker, BUZZ CARMICHAEL, decided JoeZoShow would be the subjects of his next film. Come see a live documentary performed and filmed right before your very eyes.

(Facebook Event)


See you soon!