One of my year-long wishes came true this past weekend, and in the most exciting way possible. Throughout November, the fiftieth anniversary of “Siskel & Ebert” was celebrated at the Chicago Cultural Center with special free programming hosted in its Claudia Cassidy Theater. Most of these were screenings of critically acclaimed films, followed by a conversation with key people involved in the series.
What made the “Siskel & Ebert” anniversary event held last Saturday, November 22, particularly special was the fact that it was a live show. Local actors Stephan Winchell and Zack Mast appeared on the Claudia Cassidy Stage as an iconic critic duo in a new show designed by Paul Durica’s public history project, Pocket Guide to Hell. Sitting in chairs that would have been right at home on Siskel and Ebert’s balcony, the critics watched filmed reenactments of various key moments in the evolution of their show as it gradually became a cultural phenomenon. They then discussed and debated the content of the footage, as they would the merits of the films they reviewed on their show. A fun gag centered around Ebert’s insistence that his name should have been placed first in their show’s title, given that he won a Pulitzer Prize, leading Siskel to flip a coin (as he did in real life) to ensure his name would stay before his co-host’s.
It was last July that I first saw the actors play these roles in Katlin Schneider’s play, “Siskel/Ebert,” at the Bughouse Theater in Chicago. Watching the series was as close as possible to watching Gene Siskel and Roger Ebert debate the merits of cinematic works in person. There was no doubt in my mind that the actors’ performances deserved two very enthusiastic commendations. Winchell was perfect and very funny as Siskel, while Mast captured Ebert’s look, mannerisms, and cadence so impeccably that it was downright eerie. The episode they lovingly and ingeniously recreated was from June 1987, where training colleagues were arguing about “Full Metal Jacket” and “Benji the Hunted,” with hysterical re-enactments of selected film clips. Siskel’s widow, Marlene Iglitzen, was in attendance and the show also gained her approval. From that point on, I was determined that Roger’s widow, my former boss and dear friend, Chaz Ebert, would also see the show.
When I learned that Winchell and Mast were reprising their roles for the fiftieth anniversary festivities, I knew it would be a show I couldn’t miss. Many Windy City legends who played key roles in Siskel and Ebert’s legacy were on hand for the sold-out show, including Marlene Iglitzen and Chaz Ebert; the precious producer of the series, Thea Flaum; Michelle McKenzie-Voigt, assistant director of the show in its iteration called “Sneak Previews”; and old Chicago Sun-Times film critic and columnist Richard Roeper, who was chosen as Ebert’s co-host after Siskel’s death in 1999. This distinguished group participated in a lively onstage panel discussion moderated by veteran Chicago journalist Rick Kogan after the performance, although it was earlier in the evening when Chaz audibly gave his review of the show. As soon as Mast turned to the audience, her resemblance to her late husband was so uncanny that it caused Chaz to exclaim, “Oh my God! Later in the series, when the actors had a heated argument on stage in person, it was so evocative of Siskel and Ebert’s unrivaled banter that it drew applause from the crowd.

Produced by Durica and Meredith Milliron, the show featured live performances by Jeffrey Thomas and his band of the various theme songs used by Siskel and Ebert, culminating with the theme “Sneak Previews” for which a band member heroically replicated the wall-to-wall whistling. Rachel Wilson and Tim Sozoko appeared in the reenactment footage as Thea Flaum and David Letterman, respectively, while Kenya Merritt, acting commissioner of Chicago’s Department of Cultural Affairs and Special Events, kicked off the event by reading her statements as well as those of the city’s Mayor, Brandon Johnson.
“By examining films through accessible and authentic conversations, they transformed the way the world engaged with cinema,” Merritt said of Siskel and Ebert. “As we celebrate their 50-year legacy, we also honor the generations of filmmakers, critics and audiences they inspired. Their influence continues to shape how we promote storytelling and creative innovation here in Chicago.”
As Roeper noted during the post-show panel, the spirit of Siskel and Ebert can be found in every person you see engaging in passionate conversation about the movie they just saw. The imprint of their influence can be found everywhere, from Letterboxd and Criterion Closet to a show like ESPN’s “Pardon the Interruption,” which Roeper says was intended as a sports equivalent of “Siskel & Ebert.” Chaz hinted on stage that Critics’ Legacy is the subject of several projects currently in development, including a documentary and narrative film (details on both are confidential) and a stage production actively in development by his daughter, Sonia Evans. Whether or not Winchell and Mast are involved in any of these future projects, they have set the bar extremely high for any artist seeking to capture the essence of these fiercely opinionated icons.
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