The theater critic Jack Helbig was famous for withering capsule theater reviews in such publications as Newcity and the Chicago Reader, demolishing productions he found wanting in a pithy sentence. He famously called one show “the worst thing that happened in Chicago since the St. Valentine’s Day Massacre” and, in an apocryphal story that became legendary in Chicago theater circles, and that Helbig loved, a famous playwright once hurled a retaliatory insult across a crowded room that compared Helbig to an equine appendage.
“Just who is Jack Helbig anyway?” wrote an apoplectic reader to the Reader in 1995. “Has he ever written a positive theater review for your paper? If he has, I’d love it if you would reprint it to prove it to me.”
That letter writer was wrong; Helbig just had to like the work.
Helbig died Tuesday at the age of 66 in an Oak Park hospital, after the big-hearted critic had a heart attack. His death was confirmed by his wife, Sherry Kent.
His work came with another side, one of intense intellectual curiosity and deep empathy for Chicago artists and their struggles for excellence. He also had a decades-long fascination with risky theater and improvisational comedy and with the creative Chicagoans who produced such work here across the last quarter of a century.
And in a profession famed for its judgmental, competitive personalities and long-held grudges, Helbig was a journalistic anomaly: a generous, ego-free, warm-hearted spirit who enjoyed artists and other writers and who often became friends with the very people whose work he may have loved or may have annihilated.
Helbig was a sometimes playwright and trained improviser himself, so he understood the artist’s life better than most. He showed up at show after show after show, which was always appreciated. He was an inveterate defender of the small and struggling. And, with a smile a constant presence on his lips, he was fun to be around.
“Jack just wanted people to appreciate him for who he was,” said Kent.
Indeed, many did.
Helbig was also an English teacher, eventually rising to a beloved department head over a 17-year career at Chicago’s Holy Trinity High School; many students have written affectionate tributes on social media. Since 2022, he had taught English at Rochelle Zell Jewish High School in Deerfield. “He was super-invested in being a great teacher,” Kent said. “And he was completely dedicated to teaching, even as he also wanted to be known as a writer.”
“I think everyone in Chicago theatre experienced a bad review from Jack Helbig,” said Kelly Leonard, vice president and longtime creative force at Second City. “That’s what happens when you encounter a critic with integrity. By the same token, he was more than happy to sing your praises in the next review and follow that up with a feature to help draw more attention to your work. Jack was so full of honesty and joy within his role in the theater community, you couldn’t help but want to make him proud.”
For some theaters that became highly influential in American entertainment, Helbig’s early support in the 1990s was crucial. “Jack helped put the Annoyance Theatre on the Chicago theater map,” said Mark Sutton, an early ensemble member. “He was a fan of our theater, but he never let that impact his reviews. He was always fair and insightful.”
“A Helbig pan always had bite and humor,” wrote the longtime Chicago theater actor and writer Paul Slade Smith. “And a positive review from him felt like a victory.”
Helbig also wrote over the years for the Daily Herald and the Wednesday Journal in Oak Park. He as born in October 1958 in St. Louis, graduated from the University of Chicago in 1980 and later completed a master’s degree in education at the University of Illinois at Chicago. His real name was Edward Helbig III, but Jack was adopted, Kent said, possibly to avoid confusion with his father and possibly in tribute to “Jack” Kennedy.
Kent said she met the man who would become her husband when she worked on a guidebook, “Sweet Home Chicago,” in the 1980s and engaged him to write about the theater. Things went from there. “Jack could massage any prose,” Kent said. “He was a true word doctor. And he was brilliant, creative and funny.”
“Jack just wanted to help people succeed,” said Brian Hieggelke, the editor and publisher at Newcity. “He was never driven by ambition or money, but by making his part of the world better.”
In a Chicago Reader review of “Kinky Boots” at the Paramount Theatre in Aurora right after the pandemic, Helbig wrote gorgeously of the return of the art form he loved but also was uncharacteristically self-descriptive, accurately describing himself as “a once-young, hip iconoclast, known for sharp-tongued reviews, who slowly over the many years of writing became less, well, young and eventually became less often recognized for his sharp opinions than for his fan-boggling resemblance to George R.R. Martin.”
Along with Kent, survivors include the couple’s daughter, Margaret Helbig, and a sister, Jordan Kirk. A memorial service is planned.
Chris Jones is a Tribune critic.
cjones5@chicagotribune.com
