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A Daily Guide to Chicago Comedy Shows in January

Like last month we've got another set of shows - one for (almost) every night of the month. So let's go directly into it:

January 4: High Dive: A Stand Up Comedy Show at High Dive

This weekly stand-up show at High Dive in Ukranian Village starts at 8:30 and features a consistently strong line-up of Chicago comics. Tonight's show is hosted by Bobby Condon and features the great Erica Clark headlining.

January 5: Steven Castillo's Superbowl Halftime Show at The Crowd Theater

Chicago comedian (and "certified hunk") Steven Castillo - who formerly performed as Steven King - is now a writer for "Saturday Night Live" and coming back into town to do a sketch halftime show a month before the superbowl at The Crowd Theater. In 2016 I saw him in Nick Vatterott's "The Outer Zone" at The Hideout and he absolutely killed. Based on his resume - which, aside from writing for "SNL," includes opening for Eric Andre - the assumption can be made that he's still killing it.

January 6: Friends with 401(K) Benefits: A Team Us Comedy Special at CH Distillery

Trio Tyler Fowler, Meghana Indurti, and Vik Pandya are Team Us Comedy, a group of comedians who produce shows in Chicago (including the monthly shows "Laugh Near Minimalist Furniture" and "Cocktails & Humor"). "Friends with 401(K) Benefits" is their first live special taping. Don't miss it: they're donating part of the proceeds to charity and it's hosted by Chris Trani.

January 7: Ladies Night Out Comedy Jam 5 at Riddles

This monthly show at Riddles Comedy Club started in September and has been going strong every month since. It promises "something special for the ladies to sit back relax and unwind." And with four Chicago comedians on the line-up - Jesnaira Baez, Rodney Lumpkins, T. Murph and Kool Bubba Ice - they're not just talking about the apple martini special.

January 8: Smart Mouth Open Mic at North Bar 

Started just over a year ago, this weekly open mic at North Bar is hosted every Monday night by Mary Jordan and Andrew Tavin (who also run the comedy trivia show "Are You Smarter Than a Comedian?"). Smart Mouth features 20 spots for comedians to test new material and refine their best stuff. This will be their first show of 2018 - so if your resolution involved making your Mondays more exciting get out to North Bar and work your own material.

January 9: Booth Comedy Hour at Elbo Room

Hosted by Amy Nico Schwartz (who opened for both Just Nesh and Laurie Kilmartin at Zanies last year) and Matthew Patrick Torres (who co-hosts the podcast "15 Minute Break"), this monthly stand-up show at The Elbo Room is typically held every first Tuesday of the month - the duo hosted an open mic last week so you've got a second chance to check out Booth Comedy Hour. 

January 10: Boy/Girl Sleepover at The Pony Inn

A stand-up show for everyone - including "newcomers, out of towners, open-micers, showcasers and headliners" - Boy/Girl Sleepover pops up every other Wednesday at The Pony Inn with a fresh lineup from producers Stephen Hoover, Sarah Perry and Sohrab Foroozesh. For the first show of the year Dale McPeek headlines.

January 11: This Is For You Presents: "Nostalgia" at The Promontory

Talk about a night of comedy! Tonight, The Promontory hosts two shows under the title This Is For You Presents: "Nostalgia", each hosted by a top-notch Chicago comic. The 7pm show features headliner Just Nesh (who recently appeared on HBO's All Def Comedy) and the 9pm show features headliner T. Murph (who hosts "Faded" at The Revival). Both shows are hosted by Marvin Phipps (who formerly was the house MC at Jokes & Notes).

January 12: Felipe Esparza at The Vic

Felipe Esparza won "Last Comic Standing" in 2010 and has been gaining momentum ever since. HBO recently released his stand-up special "Translate This" and he's stopping at The Vic on his Bad Decisions Tour. A second show was added at 10:30pm after the original 8pm show sold out.

January 13: The Lincoln Lodge Presents: Megan Gailey at Under the Gun Theater 

Former Chicagoan Megan Gailey just wrapped up the filming of a Comedy Central half hour last month in New Orleans and The Lincoln Lodge is bringing her to the Under the Gun Theater for two nights of stand-up to make sure Chicagoans get another chance to see her before the rest of the country does.

January 14: Julia Sweeney: Older & Wider at Second City

The consummate storyteller and "Saturday Night Live" alum (she also wrote and directed "Letting Go of God") brings her new show to Second City to workshop it. Billed as "part stand-up, part storytelling" this is a chance to see a master at work on a piece of art that isn't yet finalized. The show runs through March 18.

January 15: Ladylike at Cafe Mustache

Ladylike is described as "a storytelling show where women tell the most disgusting stories they've got." The show runs every third Monday of the month at Cafe Mustache in Logan Square and this month's show is hosted by Sarah Sherman, who is also a producer (along with Allison Dunne, Gina Gephart and Carly Ballerini).

January 16: Fried Hard Comedy Tuesdays at Island Bar and Grill

This weekly comedy show hosted by comedian Big Keef has been happening every Tuesday night at the Island Bar & Grill in Blue Island since 2013 and is still going strong. Along with a weekly line-up of killer comedians, the Island Lounge features drink and food specials along with a free after party.

January 17: Richard Lewis at Zanies

With more than four decades of comedy under his belt, comedian/actor/author Richard Lewis has earned the placement in the "Legends of Comedy" series that Zanies has booked him under. The 70 year old comic wraps up his "The Tracks of My Fears" tour with these Chicago gigs, at the iconic Wells Street location on the 17th and 18th and in Rosemont on the 19th and 20th.

January 18: Wham City Comedy and Helltrap Nightmare at The Hideout

As part of the Tomorrow Never Knows festival catch these two psychotically funny (funnily psychotic?) comedy shows - Baltimore's Wham City Comedy and Chicago's Helltrap Nightmare - combining forces and potentially ripping a hole in the space-time continuum that causes their show to play on repeat for all eternity. Imagine how disappointed you'll be if that actually happens and then you're one of the people stuck outside of the Hideout for all eternity just hearing the delightedly tortured (torturedly delighted?) screams from the audience FOR. EV. ER....

January 19: Josh Fadem at The Hideout 

Actor/Comedian/Writer Josh Fadem is also performing at The Hideout as part of the Tomorrow Never Knows festival - yes, they have an incredible comedy line-up for what on its face seems to be a music festival. Fadem is featuring two openers from Chicago: Grace Thomas (who writes for "The Onion") and Nicky Martin (aka The Great Ghouldini)!

January 20: DG Taught Me Comedy Show at Harold Washington Cultural Center

Dick Gregory - who died last August at 84 - is a legendary stand-up comic who broke through the racial divide in comedy when he performed at the Playboy Club in Chicago on January 13, 1960. 58 years later and the late comedian's manager, booking agent and travel companion Zoe Marsh-Leigh is starting a series of shows in his honor. The first show has a crazy good line-up: Jessica "Jess Hilarious" Moore, Just NeshHaha Davis, BlameItOnKway, LaLaSizaHands, Sheedz and Zana'P.

January 21: The Kiki at Transistor Chicago

The subtitle for this show - which pops up at Transistor Chicago every first and third Sunday of the month - is "Queer Comedy with Variety." The line-ups feature all kinds of performers, from comics to storytellers to improvisers to musicians, but the purpose is always the same: to have a kiki (defined as "a party including good music, good friends, and dishing the dirt with the purpose of reducing anxiety and stress."). Just the kind of show we could use in early 2018.

January 22: Master Debaters at The Comedy Bar

If yesterday's The Kiki left you feeling too relaxed come check out the exact opposite at The Comedy Bar: a comedy show with the express purpose of arguing for the sake of arguing. More specifically, this is a game show format where stand-up comics argue various unimportant points with each other and the audience decides who made the best case.


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