Chicago

South Side Farewell To Tom Dreesen, The Comic Who Opened For Sinatra

AI Assisted Icon
Published on June 17, 2026
South Side Farewell To Tom Dreesen, The Comic Who Opened For SinatraSource: Unsplash/Tim Umphreys

Tom Dreesen, the Chicago-born stand-up comic who spent more than a decade warming up the crowd for Frank Sinatra, has died, his family announced. He was 86. The family said he passed at 5:50 a.m. Wednesday and shared that "he wanted you all to know how much joy you brought him through the years."

According to ABC7 Chicago, the family wrote, "We regret to inform you that Tom has passed away this morning at 5:50 a.m." The outlet also reported that the Museum of Broadcast Communications and other colleagues quickly posted condolences on social media, turning timelines into a kind of digital wake.

Tim and Tom: A Pioneering Duo

Dreesen grew up in Harvey on Chicago's South Side and first broke through nationally when he teamed with Tim Reid to form Tim & Tom, widely described as the country's first biracial comedy duo. Their early grind on the nightclub circuit, along with the racial tensions and challenges they ran into, is chronicled in an excerpt hosted by the University of Chicago Press.

Sinatra's Opening Act

Dreesen's official biography notes that he toured the country for 13 years as Frank Sinatra's opening act and logged dozens of national TV appearances along the way. According to Tom Dreesen's official site, he appeared on The Tonight Show more than 60 times and was a regular presence on Letterman, swapping road stories and deadpan punchlines.

Tributes soon began to roll in online. The Museum of Broadcast Communications wrote that it would miss him and extended condolences to his loved ones, as reported by ABC7 Chicago. Comedians and fans shared memories across social platforms, many of them recalling his well-worn Sinatra tales and the decades he spent working clubs and theaters across the country.

Dreesen recapped that long road in his memoir Still Standing, published in 2020, and for years he hosted the Tom Dreesen Celebrity Classic charity golf event, both noted in his official biography and in book listings. The memoir is available through booksellers, including Barnes & Noble, which lists the Post Hill Press edition.