Name: The Best of the Second City: 65 Years of Funny
Start: 2025-02-22T21:00:00Z
Location: Chicago Mainstage

Chicago

Find out for yourself why The Second City has been the first name in laughter for 65 years! From the stages that launched the careers of Tina Fey, Stephen Colbert, Steve Carell, Keegan-Michael Key and more comes the next generation of comedy superstars.
The Best of The Second City features some of the best sketch comedy and songs from our comedy vaults updated for the modern era, as well as some of our newest classics and our trademark improvisation performed by The Second City Touring Company’s best and brightest…and funniest!
Group of 16 or more? We’ll make it easy—reach out to <a href="mailto:groupschi@secondcity.com" target="_blank" rel="noreferrer noopener">groupschi@secondcity.com</a>

Chicago Mainstage

We welcome all guests 13 years of age and older, but minors must be accompanied by an adult. Please note show rating for guidance on language and innuendo.

Age Requirement 13+

The Second City gives every show a rating to help patrons understand if content is appropriate for younger audiences. We welcome all guests 13 years of age and older, but minors must be accompanied by an adult. R rating is due to language and inneundo. Our shows take place in a night club atmosphere where alcohol is served.

Rated R

A sketch is a short, scripted comedy scene. Think Key and Peele or SNL. Some people might call it a "skit," but we never do. Chicago is the home of modern sketch comedy, and today, you can experience it at all Second City locations.

Sketch Comedy

The Best of the Second City: 65 Years of Funny

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Ever heard of this show &#8220;Hamilton&#8221;?
Shamilton is just like that, but (ahem) better! Expect the same level of hip hop, incredible songs, moving storytelling, stunning choreography and powerhouse singing&#8230; except made up on the spot.
The New York Times called Shamilton “One of the top 5 comedy shows to catch”.
Comedy supergroup Baby Wants Candy presents &#8220;Shamilton!&#8221;, the Hamilton-inspired hip hop improvised musical created in 2016 in LA and playing to sold out crowds all over the place, including the Kennedy Center in DC, a national touring company and weekly sold out shows in New York and LA.
Join the Shamilton cast as they improvise an epic musical based on a historical figure or celebrity of your choosing&#8230;including Genghis Khan, Kim Kardashian, Mr. Rogers, or even basketball playing superdog Air Bud. You decide!
It&#8217;s the show Lin-Manuel Miranda calls, &#8220;cease and desist!&#8221;

SHAMILTON, THE IMPROVISED HIP-HOP AMERICAN MUSICAL!

Have you ever wanted to escape? The Second City presents the 112th Mainstage Revue The Devil is in the Detours, a hilarious and unhinged descent into a dimension where chaos reigns. Join our electric six-person ensemble as they sing, dance and rock the hell out in this interactive and immersive sketch and improv comedy revue.  Don’t miss out on the wildest comedy experience of your life.
Group of 16 or more? We’ll make it easy—reach out to <a href="mailto:groupschi@secondcity.com" target="_blank" rel="noreferrer noopener">groupschi@secondcity.com</a>

The Devil is in the Detours – The Second City Mainstage

Step behind the velvet curtain into The Second City e.t.c., a lavish comedy speakeasy where the only rule for the evening is laughter. Outside, it’s winter. But here, the show is so hot and hilarious, it’ll melt away your troubles. This interactive world of illusion, decadence, and the illusion of decadence invites you to join in on a heist of hijinx sparkling with sketch, song, and improv spontaneity. The best kept secret? You are the most important part of the show. Join us and find delight. Right this way, your table’s waiting.
Group of 16 or more? We’ll make it easy—reach out to <a href="mailto:groupschi@secondcity.com" target="_blank" rel="noreferrer noopener">groupschi@secondcity.com</a>

Best Kept Secret: Tell Everyone

Cue the laugh track because it&#8217;s a very special episode of your favorite long running tv show! The gang gets up to the same &#8216;ol wacky shenanigans that you remember in this one hour comedy show performed in front of a live audience (that&#8217;s you!) but this time it&#8217;s completely made up on the spot! Watch all the will-they-won&#8217;t-theys, loveably bad bosses, and zany next door neighbors that tv raised you on now with much lower budgets!

Improvised Sitcom

After getting a single suggestion, the cast of six professional comedians asks the audience to choose a detective. Enjoy as they invent a tale of crime, secrets, and scandals right before your eyes. The performers will keep track of facts, follow leads, and conclude who is the murderer, all while you take in a comedy experience unlike any you’ve seen before. During the show, they’ll employ the tropes, character archetypes, and influences of Hercule Poirot, Miss Marple, Sherlock Holmes, Nick and Nora Charles, Encyclopedia Brown, and just a dash of Scooby-Doo.

Clued In

Chicago giving you the winter blues? The Black Excellence Revue is here to bring much-needed warmth. Brimming with brand new songs, sketches, and – of course- The Second City’s world-renowned style of improv, this cast of future stars are delivering an unforgettable night. The Black Excellence Revue is more than a comedy show – it’s a celebration of Black Joy. And, just like at the Apollo, you are a part of the show.
Group of 16 or more? We’ll make it easy—reach out to <a href="mailto:groupschi@secondcity.com" target="_blank" rel="noreferrer noopener">groupschi@secondcity.com</a>

We Always Bounce Black: A Black Excellence Comedy Revue

Step into the villa where the heat is real, the connections are unpredictable,and it&#8217;s all improvised. Love-Prov Island is a completely improvised parody of your favorite dating shows, blending romance, betrayal, and absurdity into a night that will make you wish you could put the episode on replay. This Don&#8217;t Quit Productions show has it all &#8211; bombshells, drama, vibes, pulling people away for a chat, good banter, and confessionals. Audience suggestions will shape the chaos, ensuring every episode is unique and as wild as your imagination. Will they find true love—or just make it through the next elimination? Either way, come enjoy this high-stakes, love-fueled spectacle.

Prov Ur Love 2 Me

In this Valentine&#8217;s season themed extension of Onward and Overwhelmed, the Onward cast navigates the perils of dating, loneliness, and the general overwhelming feelings that confront us every day through sketch comedy, improv, and music.

Onward and Out of Your League

Millennials take on Generation X in a battle to see which generation is funnier. The audience votes at the end of the show. Featuring some of the best comics in Chicago, Hosted by Todd Glover

Second City Productions

The Best of the Second City: 65 Years of Funny

Quick Facts

90 MINUTE RUN TIME

RATED R

In Theater Dining

In Theater Dining

Venue

Chicago Mainstage

Tickets starting at $39

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About Us

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Second City Productions

The Best of the Second City: 65 Years of Funny

Quick Facts

90 MINUTE RUN TIME

RATED R

In Theater Dining

In Theater Dining

Venue

Chicago Mainstage

Tickets starting at .css-722v25{font-weight:var(--chakra-fontWeights-bold);}$39

Next Available Showtimes

Follow us on Social

Tickets starting at $39