Second City Cast. Photo: Timothym Schmidt
The Best of The Second City, an unforgettable evening from the world’s most influential name in comedy. This high-energy performance draws from The Second City’s rich archive, bringing together iconic material and fresh perspectives for a dynamic, contemporary showcase.
From the stages that launched stars like Tina Fey, Stephen Colbert, Steve Carell, and Keegan-Michael Key, this production blends signature improv with hilarious songs, beloved characters, and timeless sketches. Each piece is crafted by some of the sharpest comedic minds and reimagined by today’s boldest voices.
With its signature mix of wit, satire, and spontaneity, The Best of The Second City captures the spirit of a company that continues to shape the comedy landscape. Join us at Guild Hall for a night of smart, fearless humor and nonstop laughs.
CAST: Aaron Alicea, Kristen Aviles, Deb Duncan, Max Kantor, Audrey Schiffhauer, Ross Taylor
MUSIC DIRECTOR: Mel Owens
Program may contain adult or mature content.
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The Second City
The Second City opened its doors in 1959 as a small comedy cabaret and has since grown to become the world's most influential name in improvisation and comedy. Celebrating its 65th year in business on December 16th, 2024, The Second City's stages, Touring Companies, and Training Centers across North America have proudly been the launch pad and artistic home for many of the funniest performers, writers, directors, and comedy creators on the planet. Our illustrious alumni list includes names such as John Belushi, John Candy, Chris Farley, Tina Fey, Keegan-Michael Key, Eugene Levy, Tim Meadows, Bill Murray, Mike Myers, Suzy Nakamura, Catherine O'Hara, Amy Poehler, Gilda Radner, Sam Richardson, Joan Rivers, Amber Ruffin, Jason Sudeikis, and Steven Yeun, among countless others. The Second City has been the first name in laughter for over sixty years.
For more information on The Second City, visit www.secondcity.com and follow The Second City on TikTok, Instagram, Facebook and Twitter.
Second City Touring. Photo: ECE Touring
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Aaron Alicea
Aaron Alicea (he/him) is from the infamous Long Island, NY. He started doing standup in Columbus, OH in 2019, then moved to Chicago during the pandemic in 2021 (surprisingly an awful time to make such a massive life transition) and began exploring other comedy mediums.He has vast performance experience in improv, sketch writing, acting, and music from several theaters he calls home, like The Annoyance Theatre or The Pack Theater in LA. He has performed in hundreds of shows around the country, was a recipient of the Bob Curry Fellowship at Second City in 2023, is currently on the all-Latine comedy troupe Escándalo at iO Theater, and is working on several projects he’s excited to show you all. Follow this goofy, unmedicated Sagittarius on Instagram @theaaronalicea for updates. P.S. he loves his mom, dad, and siblings for all of the unending support and patience in him“figuring it out”.
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Kristen Aviles
Kristen Aviles (she/her) is from the beautiful sunshine place of Staten Island, NY. After moving to Chicago in 2017 she is now a Chicago based comedian, improviser and beautiful singer. You can currently catch her sometimes in Clued-in (Second City), Shamilton (SecondCity), The Mermaids (Annoyance) or as an understudy for Alex Bellisle in Great Altercations right here in the e.t.c! If you want to follow along and see where she will be next, you can follow her on everything @kris10aviles. -
Debra Duncan
Debra Duncan (she/her)is so excited to be performing with The Second City! She’s a comedian, actress and musician proudly hailing from Akron, OH. She’s understudied for Mainstage revues Together at Last, Do TheRight Thing, No Worries If Not and Don’t Quit Your Daydream and is currently understudying for The Second City National Touring Company. She also co-produces and hosts the podcast, Queer Movie Night and can be seen performing at Logan Square Improv. She also has a band with her wife, The Q’s and you can check out their album, "Us Who Know," which is available on all streaming platforms! Follow her on Instagram @debradbag and @debraduncan on Twitter. Thank you to her best friend and love of her life, Kayla and their pup, Bea. -
Max Kantor
Max Kantor (he/him) is an actor, writer, and comedian from Atlanta, Georgia. A student and graduate of both the Second City Conservatory and Annoyance Class Program, Max can be seen performing weekly in the Holy F*ck Comedy Hour (Annoyance Theatre) and around town with his improv duo M&M, improv team You Seem Like, and comedy group Chicago Live Improv Club.Max attended Georgia State University and is repped by Grossman & Jack Talent. Also, he’s a huge fan of the Miami Dolphins and his favorite food is the sandwich!
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Audrey Schiffhauer
Audrey Schiffhauer (she/her) has been improvising and writing and producing sketch comedy in Chicago for over ten years. She has had the privilege of performing on improv team sat the iO Theater, CIC Theater, Logan Square Improv and more. Audrey is originally from Buffalo, NY (Go Bills!), and her cat Lily could not care less about any of her accomplishments. -
Ross Taylor
Ross Taylor (he/him) is originally from St. James, Missouri and studied theater at Mizzou. Favorite Second City credits include: National Touring Company, performing at the Kennedy Center and Lyric Opera and understudying the e.t.c. Ross teaches improv at the Second City and Annoyance Theater, and performs weekly at the Annoyance with Missed Call and Tuesday Musical Improv. @rosstaylornyc
Sponsors
Performing Arts programs are supported by 2026 season sponsors Galia Meiri-Stawski and Axel Stawski, with additional lead support from Henry and Peggy Schleiff, The Melville Straus Family Endowment, Monica and Peter Tessler, and Vital Projects Fund.
Guild Hall’s Performing Arts programs are made possible by the New York State Council on the Arts with the support of the Office of the Governor and the New York State Legislature.
Additional support provided by Friends of the Theater: Natascia Ayers and Jim Ciquera, Bonnie and Joel Bergstein, Gene Bernstein and Kathy Walsh, Amy Cooney and Marty Feinman, John and Joan D’Addario, Suzanne and John Golden, Hilarie and Mitchell Morgan, Steve and Susan Pesner and Peace, in memory of Michéle Pesner, whose entire life was devoted to all aspects of culture, The Schaffner Family Foundation, Lisa Schultz and Ezriel Kornel, Stacey and Oliver Stanton, and Susi and Peter Wunsch.