Tom Dreesen, the Chicago area native who rose from south suburban Harvey to become one of America’s most successful stand-up comedians and Frank Sinatra’s longtime opening act, has died at age 86.
Born in Chicago and raised in Harvey, Illinois, Dreesen grew up in a working-class family as one of eight children. After serving in the U.S. Navy and working a variety of jobs, including as an insurance salesman, he discovered his talent for comedy and began a journey that would eventually place him among the most recognizable stand-up performers of his generation.
His breakthrough came through an unlikely partnership with future actor and television star Tim Reid. Meeting through a Harvey Jaycees program in the late 1960s, the pair formed Tim and Tom, widely regarded as the nation’s first interracial comedy duo.
At a time when race relations dominated national conversations, Tim and Tom used humor to address difficult social issues while performing in clubs across the country, including Chicago’s famed Mister Kelly’s. Their act earned national attention and opened doors for future generations of comedians.
Although the duo eventually went their separate ways, Dreesen’s career continued to flourish. He became a fixture on late-night television, making approximately 60 appearances on The Tonight Show Starring Johnny Carson and numerous appearances on Late Night with David Letterman. Over the course of his career, he logged more than 500 national television appearances.
Dreesen achieved perhaps his greatest visibility through his close relationship with Frank Sinatra. Beginning in 1983, he spent 14 years touring as Sinatra’s opening act, performing before audiences around the world. What began as a professional relationship evolved into a deep friendship, with Dreesen often describing Sinatra as both mentor and father figure.
His years with Sinatra became a defining chapter of his career and later inspired his memoir, Still Standing: My Journey from Streets and Saloons to the Stage, and Sinatra.
Beyond stand-up comedy, Dreesen built a successful acting career with appearances in television and film, including Columbo, Murder, She Wrote, WKRP in Cincinnati, Spaceballs, The Rat Pack and Trouble with the Curve.
Despite decades in Hollywood and on national stages, Dreesen remained closely connected to his Chicago roots. In 2008, he reunited with Reid to co-author Tim and Tom: An American Comedy in Black and White, chronicling their groundbreaking partnership and the cultural barriers they challenged through comedy.
For Chicago’s entertainment community, Dreesen’s legacy extends beyond his television appearances and celebrity friendships. He was a trailblazer who helped redefine what stand-up comedy could be, proving that humor could bridge divides while opening doors for others who followed.
Dreesen is survived by his daughters, Amy and Jennifer, and seven grandchildren, and was preceded in death by his son Tommy.
He was 86.
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