- June 30, 2026
- Updated 7:33 pm
Remembering Tom Dreesen: Comedian, Storyteller, Friend
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- admin
- June 17, 2026
- Celebrity News Entertainment
Tom Dreesen, known for his comedic talent and storytelling, passed away at 86 after battling cancer. He had an illustrious career, making over 500 television appearances, including 61 times on ‘The Tonight Show.’ Dreesen was a favored opening act for celebrities like Smokey Robinson, Liza Minnelli, and notably, Frank Sinatra. He opened for Sinatra for 13 years and served as a pallbearer at his funeral.
David Letterman, a close friend, once praised Dreesen: ‘He is one of my oldest friends and a born storyteller. And he’s got such a good heart.’ That heart unfortunately stopped early Wednesday morning in a California hospital.
Early Life and Challenges
Dreesen was born on September 11, 1939, as the third of eight children. He grew up in Harvey, Illinois. His childhood was marked by poverty; the family lived in a shack without basic amenities. Dreesen left high school early and joined the Navy, traveling around the world. Afterward, he worked long hours to support his family, often spending time afterward reclaiming a sense of youth by playing basketball and softball.
The Rise of a Comedy Talent
His involvement with the Jaycees introduced him to Tim Reid, and together they formed an interracial comedy duo called ‘Tim & Tom’ in 1969. They performed in various Chicago nightclubs. However, despite their popularity, they never broke into the financial big leagues, splitting their largest paycheck of $750.
In 1974, Reid moved to Los Angeles, leading to the duo’s breakup. Following suit, Dreesen also moved to Los Angeles, enduring a tough start that saw him living in an abandoned car, washing in gas station bathrooms, and surviving on a meager $1 per day.
Success in Entertainment
His persistence paid off at The Comedy Store, which opened doors to new opportunities. Dreesen built a reputation among fellow comedians like Letterman, Leno, and Robin Williams. This camaraderie extended to job opportunities, such as warming up the crowds for TV game shows.
His major break came with ‘The Tonight Show,’ leading to a development deal with CBS and opening acts alongside famed stars, including an $8,000 per week gig in Las Vegas. His relationship with Sinatra began with an introduction by Sinatra’s lawyer, Mickey Rudin, and blossomed into a long-standing professional partnership and friendship.
Later Years and Legacy
After Sinatra’s passing, Dreesen continued performing, including a popular autobiographical show, ‘Shoeshines to Sinatra.’ He was notable for his philanthropy, with many benefits performed without any fees, a testament to his generous nature.
Dreesen, a Cubs fan, often returned to Chicago and was a familiar face at local events. Tributes poured in upon his passing, highlighting his influence and lasting friendships. Steppenwolf ensemble member Gary Sinise and restaurateur Steve Lombardo expressed their admiration for him. He also held a significant role in the Gary Sinise Foundation.
Dreesen’s life story includes the revelation late in life about his biological father, illustrating the complexities of his earlier years. Despite challenges, Dreesen led a fulfilling life, surrounded by friends and family. His memorial service is being arranged, celebrating his remarkable legacy.
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