Tom Dreesen, the beloved comedian whose career spanned more than five decades and took him from humble beginnings in suburban Chicago to the biggest stages in entertainment, has died at the age of 86.
Served in the U.S. Navy
The legendary performer passed away after a long battle with cancer, according to friends and family. His death marks the end of an extraordinary career built on laughter, perseverance, and a genuine love for people.
In a statement shared with People, Dreesen’s family reflected on the impact he had on audiences across America.
“For more than five decades, Tom Dreesen brought laughter, heart, and humanity to audiences across America. A proud native of Harvey, Illinois, Tom built a remarkable career through perseverance, talent,” they wrote.
Born in Chicago in 1939 and raised in nearby Harvey, Dreesen served in the U.S. Navy before eventually finding his way into comedy. While working as an insurance salesman, he met future collaborator Tim Reid. Together, they formed what is widely recognized as one of America’s first interracial comedy teams, breaking barriers during a turbulent era in American history.
“Together, they became one of America’s first interracial comedy duos, using humor to break barriers and open doors during a time of great social change,” the family statement noted.
Dreesen would go on to become one of the most familiar faces in stand-up comedy, making more than 500 national television appearances. Audiences embraced him through frequent appearances on The Tonight Show Starring Johnny Carson, Late Show with David Letterman, and numerous other television programs.
His career reached another level when he spent more than a decade touring with legendary entertainer Frank Sinatra. He went on to open for Frank Sinatra for 14 years.
“When you tour with Frank, you have to stay up until the sun comes out,” Dreesen recalled in a 1998 interview following Sinatra’s death.
Reflecting on Sinatra’s final concert in 1995, Dreesen remembered, “He got five standing ovations for six songs.”
Favorite memory of Frank Sinatra
The opportunity to tour alongside Sinatra became one of the defining chapters of his life. In a 2006 interview with the Chicago Tribune, Dreesen admitted he turned down major television opportunities to remain on the road with the icon.
“Every time networks came to me and said, ‘Do you want to do a series? What about a talk show?’ it would mean I’d have to stop touring with Frank. How could I do that?” he said.
David Letterman once summed up Dreesen’s talent by saying, “By any gauge, Tom is a success, the consummate pro. But might he have been even more? Well, yes. He could easily be doing what I do.”
When asked about his favorite memory from his years with Sinatra, the legendary comedian found it nearly impossible to choose just one.
“There are so many that I can never forget. Some of my favorites were the times when he would open up and share personal stories and feelings with me as we drove around the desert in Palm Springs, where he lived, sometimes driving until the sun came up. I have great memories of staying at his house, where he and Barbara always made me feel like part of the family. Frank went from being a boss, to being a buddy, to being like a father to me,” Dreesen said while speaking to The Times in 2019.
Struck with cancer over 13 years ago
Beyond the spotlight, friends remember Dreesen as a man whose kindness matched his talent. Ryan Martin, owner of Chicago’s Den Theatre, recalled Dreesen’s sold-out performance there just two years ago.
“He had a ton of energy on stage. He brought that in here. I mean this room lights up when a performer comes in and ignites it, and he definitely did that,” Martin told CBS.
The two later sat down for a podcast conversation that Martin says he will never forget.
“There’s just a lot of depth to that particular conversation that I’ll always appreciate,” Martin said. “He gave us this spirit of like real generosity and caring and fun and funny and enjoyed himself and didn’t take himself too seriously either.”
Longtime friend and former Sun-Times columnist Tom Rapoport revealed that Dreesen had quietly battled cancer for more than a decade.
“I was dumbstruck. Tom has been part of my life for 30 years now,” Rapoport told CBS. “Tom was good at hiding what was going on, you know, he was struck with cancer over 13 years ago.”
Rapoport also reflected on Dreesen’s rare ability to connect with everyone he met, whether celebrities or everyday people.
“He was at ease with everybody, with Sinatra and Dean Martin and Sammy Davis, who he toured with and all the rest, but with people from Harvey, Illinois, too,” he said.
Gary Sinise was a close friend
Actor Gary Sinise, a close friend and supporter of Dreesen’s charitable work, paid tribute shortly after learning of his death.
“This morning America lost one of our great comedians and patriots, and I lost a dear friend,” Sinise wrote on Instagram.
He praised Dreesen as “a special person” with a “tremendously charitable heart,” noting that he had served as an ambassador for the Gary Sinise Foundation for 14 years.
“He loved our country and the men and women who serve and he loved supporting them through our foundation,” Sinise said.
“Tom was hilarious, always could make us laugh, and such a good friend. I will miss him terribly. What a great long career he had in show business. Thank you, Tom. God Bless you my friend. Rest in Peace brother.”
Dreesen is survived by his children, grandchildren, and countless friends, colleagues, and fans.
“Tom Dreesen’s legacy will live on through the laughter he created, the barriers he helped break, the entertainers he inspired, and the countless lives he touched,” his family said.
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