Many opportunities over the next eight days to celebrate love and/or mock it. I’ve listed shows that promise fun with the highs and lows of Valentine’s Day, plus more of the week’s comedy highlights.
Visiting this week: Heather McDonald (Chelsea Lately), Margaret Smith (The Ellen DeGeneres Show), Jim Norton, and the Royal Comedy Tour which is Tony Rock, Gary Owen, Sommore, and Chicago’s own George Willborn and Tony Sculfield.
Ticket Alert:
Dan Harmon and Dino Stamatopoulos bring Harmontown to the Park West on February 20. Click here for tickets.
Trevor Noah is at The Chicago Theatre on March 26. His tour is selling out fast. Click here for tickets.
Update 2/10: Trevor Noah has announced a second performance on March 26 at 10:00 p.m. Tickets for this second show will be available February 12, 12:00 p.m. here.
Two comedians who grew up in Chicago and launched their careers here are in the news:
Hannibal Buress’s new special, Comedy Camisado, began streaming on Netflix on February 5.
Sebastian Maniscalco will star in Sebastian, one of fourteen new comedy pilots ordered last week by NBC. He will play a newlywed with a strong Italian family. Sebastian will co-executive-produce with Greg Garcia (My Name Is Earl, Raising Hope, The Millers).
I saw this on Tony Sco’s Twitter feed this week: the stars of Good Times have launched a Kickstarter project to fund a Good Times movie. Created in the ‘70s by Mike Evans and Norman Lear, Good Times was one of the greatest sitcoms of all time and still holds up today. It was the story of Florida and James Evans raising their children in Chicago’s Cabrini Green projects. Sadly, Esther Rolle (Florida) died in 1998. Surviving cast members John Amos (James), Jimmy Walker (JJ), BerNadette Stanis (Thelma), Ralph Carter (Michael) and Ja’Net Dubois (Willona) created the Kickstarter project. Check it out here.
Please re-confirm all details below before heading out!
MONDAY, FEBRUARY 8
Blackout Diaries at UP Comedy Club, 230 W. North Ave., 8:00 p.m. Tonight continues UP’s series highlighting Chicago’s best comedy. Hosted by Sean Flannery, a storyteller of Homeric proportions, comedians will tell their own legendary drinking stories. Audience gets to ask questions. Featured on NPR, Comedy Central and in all the major Chicago papers as one of the city’s most recommended events. ChicagoNow blogger Krista Atkinson is one of the featured comedians tonight!
3Peat at iO, 1501 N. Kingsbury, 10:00 p.m. An audience-inspired monologue which is followed by long-form improv which is inspired by the monologue. 3Peat is Nnamdi Ngwe, John Thibodeaux, Patrick Rowland, Allison Ringhand, 
Shantira Jackson, Torian Miller, Dewayne Perkins, Martin Morrow, and Chris Redd. Chance the Rapper and other surprise guests have been known to stop by.
I’ve seen Martin Morrow and Chris Redd’s stand-up and I would put money on them becoming household names. Really interested to see them do improv. I’m blown away by comedians who are adept at all comedic forms. Also, in case it comes up, Martin Morrow has an excellent singing voice.
TUESDAY, FEBRUARY 9
Sonia Denis at Women & Children First, 5233 N. Clark, 7:30 p.m. Sonia Denis headlines this month’s Sappho’s Salon which is “artistic explorations of feminism, gender, and sexuality.” Sonia Denis is honest and personal and her positive energy is contagious, even with painful subject matter. Interesting fact: she is from Washington, D.C. I grew up in D.C., but only in recent years learned how many favorite comedians were born or grew up there. In addition to Sonia Denis: Wanda Sykes, Dave Chappelle, Julia Louis-Dreyfus, Earthquake, Stephen Colbert, Lewis Black, Louis C.K., Tommy Davidson, Jermaine Fowler and Ana Gasteyer. Everyone knows D.C. has clowns, but it’s also a capital city when it comes to comedians.
If you can’t make it to WCF, Sonia Denis also headlines The Love Below showcase on Thursday at Beermiscuous, 2812 N. Lincoln Ave. at 7:00 p.m.
The Comedy Bowl at Diversey River Bowl, 2211 W. Diversey, 8:00 p.m. An evening of trivia games and comedy. This twice-monthly event is hosted by Mona Aburmishan whose comedy comes from a place of both strength and struggle. So honest and relatable. She guest-hosted Windy City Live for the first time recently and did a fantastic job. Hoping they bring her back soon.
AWK Presents: Rejected at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. “American Wonderbread Kaleidoscope (AWK) is excited to present an evening of storytelling, improv and comedy all centered on the theme of rejection and its sometimes destructive, but always formative effects. This curated, hour-long stage show aims to offer Chicago’s best local performers a chance to paint the silver lining on some of their worst rejections.”
A Love Letter to Myself at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. “An all female lineup of laughter discussing what it means to love ourselves as women and the journeys we take to get there. Self-addressed love letters will be read aloud by prominent members of the Chicago community … mixed with comedic performances by an all-female cast of top Chicago talent. If you’re an industry professional, join us before the show for FREE comedy industry speed networking to expand your network of funny women.” Click here to register for the networking event.
Snack Attack Presents Azhar Usman and Reese’s Cups at Elbo Room, 2871 N. Lincoln Ave., 8:00 p.m. Hosted by Prateek Srivastava. Featuring Bill Gevirtz, Jerry Tran, Erica Clark. Entire line-up is excellent. I saw Azhar Usman open for Maz Jobrani last year (he has also opened for Dave Chappelle over 40 times). This Skokie native and lawyer turned comedian is one of those rare performers who feels like a friend the moment he steps on stage. His comedy is about the experience of being a Muslim American, growing up with immigrant parents and family life.
Marty DeRosa interviewed Erica Clark on his podcast Wrestling With Depression here. She is a talented, interesting, engaging comedian in her own right, but she is also Mr. T’s daughter and has a lot to say about her growing up years. Wrestling With Depression is one of the most real, honest, insightful podcasts you’ll ever hear. It can be painful, too, but that just makes it all the more truthful. Highly recommend!
WEDNESDAY, FEBRUARY 10
Heather McDonald interview on Chicago’s Comedy Scene Radio at wherever you are, 8:30 a.m. Follow this link or download the CCSR app and listen anywhere. Heather McDonald, previously a writer for Chelsea Lately, infuriated her former boss by telling Hollywood Today Live that while she worked for Chelsea she “lived in fear.” She has since explained that the fear was a product of her own self-doubt. Very interested to learn more about her career and comedy. Heather McDonald appears at Park West on February 14.
“Dave Maher Coma Show” at The Annoyance Theatre, 851 W. Belmont, 8:00 p.m. Dave Maher’s one-man show about what happened when he was in a coma, eulogized on Facebook and everything that followed. If you’ve ever struggled with health stuff, this show is bound to be therapeutic and boost your will to find what’s funny even if the odds seem long. Through February 24.
THURSDAY, FEBRUARY 11
Scott Whitehair at Off Campus Writers Workshop, Winnetka Community House, 620 Lincoln Ave., Winnetka, 9:30 a.m. Tips from this multi-award winning stand-up storyteller on developing your own unique voice and presentation style.
Pre-Valentine Comedy Showcase at Carruthers Center for Inner City Studies, 700 E. Oakwood Blvd., 6:00 p.m.A fundraiser for the Alternative Schools Network with performances by B. Cole, Just Nesh, Jeremiah Frazier and Jamal Hawkins (DJ SLO).
Scott Duff hosts LGTBQ Valentine’s Day Party at Women & Children First, 5233 N. Clark, 7:00 p.m. Comedian, actor and activist Scott Duff (host of The Laugh Factory’s Chigaygo) hosts this party and discussion with author B. Proud (First Comes Love: Portraits of Enduring LGBTQ Relationships).
Be Mine at Fizz Bar, 3220 N. Lincoln Ave., 7:00 p.m. Dandelion Theatre presents a variety show of “sketch, musical improv, and a short play (A Lady Who Collects Spiders Meets a Gentleman Who Collects Snakes), all inspired by love, hate, and everything else we feel on Valentine’s Day.” There will also be a raffle of tickets from Chicago Shakes, Steppenwolf, Auditorium Theatre, Harris Theater for Dance and Music, Raven Theatre, coffee from Dark Matter, dry cleaning from New SOS Cleaners, a homemade pie, and more.
Clayton English at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:30 The winner of 2015’s Last Comic Standing. Starting tomorrow night, Clayton English’s shows at The Improv will include the option of a Valentine’s dinner package (see below).
The Valentine’s Show with Patrick O’Hara at The Zodiac Café & Lounge, 113 Main St., Crown Point, IN, 8:00 p.m. “So romantic you’ll be sick.” Comedian and fellow ChicagoNow blogger Patrick O’Hara is the special guest. Headliner: Amy Nico Schwartz. Featuring Claire Swanson. Hosted by Todd McNeeley.
Jim Norton’s “Mouthful of Shame Tour” at The Vic, 3145 N. Sheffield, 8:00 p.m. Jim Norton has appeared on The Late Show with David Letterman, The Tonight Show, Louie and Inside Amy Schumer. He is also a bestselling author (Happy Endings) and co-hosts the Opie with Jim Norton Show on Sirius XM Radio. He also really pissed off Colin Quinn once during a USO tour in Iraq where he protested the cancellation of the comedians’ shows due to incoming fire. I’m reading Quinn’s The Coloring Book: A Comedian Solves Race Relations In America, so this story was on my mind. Colin Quinn says they’re actually the best of friends, but jeez. You wouldn’t know it. Among other choice appellations, he refers to Jim Norton as a “ludicrous goblin.” ANYWAY. Check out pp. 181-187. (Loved the book, but those pages were brutal.)
Just Dickin’ Around at Hydrate, 3458 N. Halsted, 8:30 p.m. “All genders showcase. The JDA showcase has top-of-the-line Chicago comics and is “a women-run, queer-friendly showcase that provides a safe, supportive space with a positive energy for our performers and guests.” Free pizza! Co-produced by comedian, writer and ChicagoNow blogger Krista Atkinson.
Holiday with Tyler & Lucas at iO, 1501 N. Kingsbury, 10:00 p.m. A seasonal celebratory stand-up show. Tonight Tyler and Lucas host Kristen Toomey, Kristin Clifford, Joe McMahon, Josh Ejnes, Steven King and Ray Holleb.
Messing with a Friend at The Annoyance Theatre, 851 W. Belmont, 10:30 p.m. Susan Messing improvises with another talented comedy personality every Thursday night.
FRIDAY, FEBRUARY 12
Interview with Clayton English at Chicago’s Comedy Scene Radio at wherever you are, 8:45 a.m. Follow the link to CCSR or download the app to hear Tony Carr and Steve Touhy interview the winner of 2015’s Last Comic Standing.
Chicago’s Comedy Scene Radio presents Dinner and a Show at Maggiano’s Little Italy, 1847 Freedom Dr., Naperville, 6:00 p.m. Headliner: Vince Carone. Hosted by Katy Meiners. Featuring Joe Larkin and Mike Wiley.
Love Stories From the Cutting Room Floor at iO, 1501 N. Kingsbury, 6:30 p.m. “Love motivates so many of our actions, but what happens as we start to redefine it in our older and maybe-wiser years? Dina Facklis explores this through personal stories as well as the characters that intrigue her most on love’s landscape. This remount of the show will also feature an audience-focused game show where Facklis uses her special match-making skills (three of her set-ups are now married) to test out her theories of love in real life.”
The Kates at The Book Cellar, 4736-38 N. Lincoln, 7:00 p.m. All female comedy showcase led by Kelsie Huff.
Defiant Thomas Brothers at Second City, 1616 N. Wells, 7:30 p.m. I don’t know if DTB will cover Valentine’s Day tonight, but if you’re a fan of Steve Martin or Peter Sellers or Key & Peele or the best of SNL, this will be a sweet evening.
Clayton English at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 8:00 p.m. and 10:15 p.m. The winner of 2015’s Last Comic Standing. Valentine’s Day dinner included as an option at the 8:00 p.m. show.
#DATEME: An OKCupid Experiment at UP Comedy Club, 230 W. North Ave., 8:00 p.m. and 11:00 p.m. What happened when a comedian placed thirty-eight “undateable” profiles on an online dating site? A true story.
The Boys at Second City, 1616 N. Wells, 9:00 p.m. Rachael Mason and Susan Messing improvise with Norm Holly, Ryan Archibald and Craig Uhlir.
A Very Sultry Valentine’s with Kory Smith at WIP Theater, 6670 N. Northwest Highway, 10:00 p.m. Stand up with lots of love and crowd work.
SATURDAY, FEBRUARY 13
Chic-A-Go-Go David Bowie Tribute Dance Party #3 at Chop Shop, 2033 W. North, 4:00 p.m. This episode of the cable TV family-friendly dance party is #3 because Chic-A-Go-Go’s first two David Bowie tribute dance parties sold out! Jokes from Miss Mia and puppet co-host Ratso, plus much music and dancing.
MILF-Life Crisis at Second City, 1608 N. Wells, 6:00 p.m. A new comedy by Ann Marie Scheffler about the trauma of post-marriage dating.
Mortified Chicago Presents Valentine Shmalentine at Mayne Stage, 1328 W. Morse Ave., 6:30 p.m. and 9:30 p.m. Brave everyday folks get on stage and reveal the comedy and horror of love. The bravest will be accompanied onstage by their significant others.
Clayton English at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:00 p.m. and 9:15 p.m. The winner of 2015’s Last Comic Standing. Valentine’s dinner included as an option at the 7:00 p.m. show.
The Two-Hour Comedy Hour Valentine’s Day Extravaganza at Gallery Cabaret, 2020 N. Oakley, 7:00 p.m. Free showcase featuring Derek Smith, Deanna Ortiz, Cameron Gillette, Mary Zee and Matt Chiarmonte. Hosted by Andy Fleming and J. Michael Osborne.
No Boys Allowed – Sweethearts Only, ok? at Flat Iron Comedy, 1579 M. Milwaukee, 7:30 p.m. Free. “A showcase of women and other unique performers” hosted by Wes Perry. Tonight: Kate O’Connor, Danielle Susi, Becca Brown, Liz Joynt Sandberg, Katy Conroy, Sarah Shockey, Erin Kathryn Morrill and Alyson Morrill.
“My Funny Valentine” at The Laugh Factory, 3175 N. Broadway, 8:00 p.m. Valentine-themed stand-up with Jeff Arcuri, Drew Frees, Kristen Toomey, Paul Farahvar, Natalie Jose and more TBA.
Cupid Has a Heart On … In Bed at Stage 773, 1225 W. Belmont, 8:00 p.m. and 10:30 p.m. Chicago’s longest running musical comedy show. Both shows include a champagne toast and a V-Day goodie bag.
8:00 p.m. New numbers and Cupid classics
10:30 p.m.: Special, late-night one-act performance of the cast’s risqué-ist numbers.
#DATEME: An OKCupid Experiment at UP Comedy Club, 230 W. North Ave., 8:00 p.m. and 11:00 p.m. What happened when a comedian placed thirty-eight “undateable” profiles on an online dating site? A true story.
Chicago’s Comedy Scene Radio at Liquid Therapy, 3501 Channahon Rd., Joliet, 8:00 p.m. Hosted by Jordan Holmes. Featuring David Banks, Maggie Miller, Dave J and Mark Johnson.
Aquarius Valentine’s Day Show at Meyer Ball Room, 8 E. Galena Blvd., Aurora, 8:00 p.m. Hosted by Comedian Stick.
“My Nasty Valentine” at The Laugh Factory, 3175 N. Broadway, 10:00 p.m. “Raunchy and raw” Valentine-themed stand-up with Kellye Howard, Pat Tomasulo, Abi Sanchez, Kristen Toomey and more TBA.
“Yeah Buddy Awesome Time Gets Sexy” at Brainstorm Comics, 1579 N. Milwaukee, Ste. 321, 8:30 p.m. Featuring Derek Smith, Deanna Ortiz, Charlie Vergos, Todd Massey, Derek Moulds, Jon Lyons, Justin Vestal. Hosted by Jason Melton.
Your F!@$ed Up Relationship at iO, 1501 N. Kingsbury, 8:30 p.m. A long-form improv show inspired by the audience’s true relationship horror stories.
A Very Sultry Valentine’s with Kory Smith at WIP Theater, 6670 N. Northwest Highway, 10:00 p.m. Stand up with lots of love and crowd work.
SUNDAY, FEBRUARY 14
Margaret Smith: Pole Dancing and Pickup Lines at Theater WIT, 1229 W. Belmont, 6:00 p.m. and 9:00 p.m. Margaret Smith returns to Chicago, her comedy hometown, for a night of stand up and music with Natalie Gaza. Margaret Smith won the American Comedy Award for Funniest Female Stand-Up in 1995 and went on to win multiple Emmy awards as a writer for The Ellen DeGeneres Show. She appeared many times on The Tonight Show with Jay Leno and on The Late Show with David Letterman. Her movie and TV roles include Goodfellas and That 80s Show (as Margaret the Record Store Lady). Her album As It Should Be is available on her site, iTunes, Amazon and with a Spotify paid subscription. She is also the author of What Was I Thinking? How Being a Stand Up Did Nothing to Prepare Me to Become a Single Mother.
Valentine’s Day Double Feature at Under the Gun Theater, 956 W. Newport, 6:00 p.m. You can buy tickets to one or both.
6:00 p.m. “SMUT: The Improvised Romantic Book Club.” A reading of A Match Made on Main Street (part of the Briar Creek series) with author Olivia Miles
7:30 p.m. “Will You Accept This Rose?” This Bachelor parody will feature special guest and the “winner” of The Bachelor’s fifth season, Ed Swiderski.
Tuxedo Cat Comedy’s Valentine’s Day Show at Innertown Pub, 1935 W. Thomas at 7:00 p.m. With Natalie Jose, Mikey Manker, Blake Burkhart, Ashley Huck, TCC producer David Philips and special surprise guests. Hosted by TCC producer Jerry Tran.
Clayton English at The Improv, 5 Woodfield Rd., Woodfield Mall Store K120B, Schaumburg, 7:00 p.m. The winner of 2015’s Last Comic Standing. Valentine’s Day dinner is included as an option.
#DATEME: An OKCupid Experiment at UP Comedy Club, 230 W. North Ave., 7:00 p.m. and 10:00 p.m. What happened when a comedian placed thirty-eight “undateable” profiles on an online dating site? A true story.
My Funny Valentine at The Laugh Factory, 3175 N. Broadway, 7:00 p.m. and 9:00 p.m. Valentine-themed stand-up.
7:00 p.m. Jeff Arcuri, Jim Flannigan, Reena Calm, Adam Burke, Kristen Toomey and more TBA.
9:00 p.m. Kevin Williams, Lainie Lenertz, Natalie Jose, Dave Helem , Jeff Arcuri and more TBA.
Love is … at The Revival, 1160 E. 55th St., 7:00 p.m. Presented by “Done Waitin’” and hosted by Doc Love. Stand-up, games and music. Evening is for both couples and singles.
Mikey O’s Valentine’s Day Comedy Show & Concert at Joe’s Bar, 940 W. Weed, 7:30 p.m. Comedy with Vince Acevedo and Melissa Duprey. Concert begins at 10:00 p.m. with Michael Stuart and his Orchestra.
Heather McDonald at Park West, 322 W. Armitage Ave. 8:00 p.m. Valentine’s Day comedy about family, spouses, kids, step kids and maybe even some divorce fantasies. Heather McDonald wrote and contributed on-air to Chelsea Lately (and ignited controversy by saying it was a scary time) and is also the New York Times bestselling author of You’ll Never Blueball in This Town Again and My Inappropriate Life.
The Royal Comedy Tour at Arie Crown Theater, McCormick Place, 2301 South Lake Shore Dr., 8:30 p.m. With Sommore, Gary Owen, Tony Rock and Chicago’s own George Willborn and Tony Sculfield.
Singles Night With Dave at iO, 1501 N. Kingsbury, 10:30 p.m. Dave promises a night of comedy and loneliness together.
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