had a clip of him talking about Sinatra open on my laptop when the notification came through. he was telling the story about Frank being like a father to him. 86 years old, can't process that right now
Their story
Tom Dreesen was an American stand-up comedian, actor, author and motivational speaker whose career ran from the Chicago nightclubs of the late 1960s to a final network television appearance just days before his death in June 2026. He was best known as one half of Tim and Tom, the barrier-breaking…
Tom Dreesen was an American stand-up comedian, actor, author and motivational speaker whose career ran from the Chicago nightclubs of the late 1960s to a final network television appearance just days before his death in June 2026. He was best known as one half of Tim and Tom, the barrier-breaking comedy duo he formed with Tim Reid, and as Frank Sinatra's opening act for well over a decade.
Thomas Eugene Dreesen was born on September 11, 1939, and grew up in Harvey, Illinois, a south suburb of Chicago. He was the third of eight children of Glenore Dreesen, a waitress, and Walter Dreesen, a steelworker who played trumpet in a band. The family was desperately poor, living for a time in a shack behind a factory, and both parents struggled with alcohol. As a boy he shined shoes in local taverns and caddied at golf courses to help feed his brothers and sisters, and he later said that watching his uncle tell jokes from behind a bar first drew him to comedy. He attended Thornton Township High School but did not graduate, and at 17 he enlisted in the U.S. Navy, serving four years.
Back in Illinois he married Maryellen Subock in 1958, raised three children, poured concrete and sold insurance. Through the local Jaycees he helped create a drug-education program for schools, and his partner in those classroom talks was Tim Reid, a young Black marketing representative. Students told the pair they were funny enough to be a comedy team, and in 1969 they became Tim and Tom, widely credited as the first interracial stand-up comedy duo in the United States. They worked Black clubs, white clubs, Playboy Clubs and lounges, faced hostile crowds and threats on the road, and split up in the mid-1970s when Reid moved to Los Angeles, where he went on to star in WKRP in Cincinnati.
Dreesen followed him west and for a time lived in a broken-down car, hitchhiking to the Comedy Store on Sunset Boulevard and begging for stage time. He became part of a remarkable class of young comics that included David Letterman, Jay Leno, Robin Williams and Michael Keaton. In 1979 he helped organize and lead the six-week strike by comedians at the Comedy Store, which ended with performers being paid for their sets.
His breakthrough came on The Tonight Show Starring Johnny Carson, and he became a frequent guest there and on Letterman's programs, appearing dozens of times across Late Night and the Late Show and occasionally guest hosting the Late Show. By his own count he made more than 500 national television appearances. He opened for Smokey Robinson, Gladys Knight, Tony Orlando, Liza Minnelli, Sammy Davis Jr. and, beginning in 1983, Frank Sinatra, touring with him for 13 or 14 years (sources differ) and becoming a close friend. He was the master of ceremonies at Sinatra's wake in 1998 and one of the pallbearers at his funeral. After Sinatra's death he toured an autobiographical one-man show, Shoeshines to Sinatra, later billed as The Man Who Made Sinatra Laugh.
As an actor he appeared in Columbo, WKRP in Cincinnati, Murder, She Wrote and Touched by an Angel, and in films including Spaceballs, Man on the Moon, the HBO movies The Rat Pack and Lansky, and Trouble with the Curve. He released the comedy album That White Boy's Crazy in 1989, co-wrote Tim and Tom: An American Comedy in Black and White with Reid and Ron Rapoport in 2008, and published the memoir Still Standing in 2020 with a foreword by Letterman.
Away from the stage he was a tireless volunteer. He emceed countless charity and sports events, hosted the Tom Dreesen Celebrity Classic golf tournament, spoke to comedians about mental health and addiction, and served for 14 years as an ambassador for the Gary Sinise Foundation, which supports veterans and first responders. In 1999 he received a Golden Palm Star on the Palm Springs Walk of Stars. A lifelong Chicago Cubs fan, he often led the seventh-inning stretch at Wrigley Field.
Dreesen kept working into his eighties, launching a podcast called Who's Tom Dreesen? and making his last television appearance on Comics Unleashed with Byron Allen on June 9, 2026. He died on June 17, 2026, in Los Angeles at the age of 86. His family did not publicly state a cause, although the Chicago Tribune reported that he had been fighting cancer. He was survived by daughters Amy and Jennifer and seven grandchildren, and was predeceased by his son Tommy. A memorial service at Forest Lawn in Los Angeles on July 9, 2026, was emceed by David Letterman, with tributes from Tim Reid, Gary Sinise, Jon Voight, Joe Mantegna, Tiffany Haddish and Byron Allen.
Biography adapted from Wikipedia; Chicago Tribune (2026-06-17); Associated Press (2026-06-17); Los Angeles Times (2026-06-18); Deadline; Variety; Chicago Sun-Times; LateNighter; WTVR; Chicago Star Media.
In their own words
“I believed in my dream.”
On refusing to give up while living in a car in Los Angeles, United Podcast, quoted by the Los Angeles Times
“If he loved you, he worshipped the ground you walked on. In a lot of ways, he was like a father to me.”
On Frank Sinatra, The Desert Sun, 2014
“No matter where I was, if I close my eyes, I see a little boy with a shoe shine box trudging through the snow in the bitter cold, going from tavern to tavern, trying to make enough money to feed his brothers and sisters. That's who I am.”
Quoted by the Los Angeles Times, 2026
“There was a mantra in the neighborhood I grew up in that you only deserve in life what you work for.”
2021 podcast appearance
“Tom was the first comedian I met at Comedy Store in 1975. We became friends immediately. He had wisdom and endless stories.”
David Letterman, tribute after his death, June 2026
“My friend and partner has left the stage. He was the kindest human being I've ever known.”
Tim Reid, tribute on social media, June 17, 2026

same, I was watching that Letterman compilation last night