For over six decades, Tom Dreesen made an indelible mark as a comedian. He appeared on television more than 500 times, including 61 on “The Tonight Show.” Dreesen opened for legends like Smokey Robinson, Tony Orlando, Gladys Knight, and notably Frank Sinatra, partnering with him for 13 years. He served as the master of ceremonies at Sinatra’s wake in 1998 and was a pallbearer at his funeral.
David Letterman, a longtime friend, praised Dreesen for his storytelling skills and kind heart. Sadly, Dreesen passed away due to cancer at the age of 86 in a California hospital.
Born on September 11, 1939, in Harvey, Illinois, Dreesen was the third of eight children. His early life was challenging as he grew up in poverty. As a child, he lived in a shack that lacked basic amenities, while his parents struggled with alcoholism. Dreesen described his childhood as “raggedy-ass poor,” with family members sometimes sleeping five to a bed and covering broken windows with rags.
Despite these hardships, he showed resilience. He caddied at golf courses, shined shoes, and attended Thornton Township High School without graduating. He eventually joined the Navy, which took him around the world for four years. During a leave, he married Maryellen Subock from Harvey in 1958. They had three children together: Amy, Tom, and Jennifer.
After leaving the Navy, Dreesen worked long hours pouring concrete. He also engaged in community work through the Jaycees, where he co-created a drug-education program for schools. Teaming with Tim Reid, they formed the interracial comedy duo, Tim & Tom, in 1969. Their act gained popularity in Chicago nightclubs before Reid moved to Los Angeles in 1974. Dreesen soon followed, briefly living in an abandoned car while trying to establish himself as a comedian in Los Angeles.
At the Comedy Store, he became part of a community of budding comics, including David Letterman and Jay Leno. Letterman acknowledged Dreesen’s guidance and credited him with helping many comedians find work.
Dreesen’s big break came with a successful appearance on “The Tonight Show.” This led to a development deal with CBS and steady work as an opening act. One pivotal moment in his career was meeting Frank Sinatra’s lawyer, which led to him becoming Sinatra’s opening act. Their professional relationship lasted for years, often filled with nights of camaraderie and discussions on life.
Following Sinatra’s death, Dreesen continued performing, especially with his show “Shoeshines to Sinatra,” and appeared regularly in clubs. Known for his charitable work, he performed many benefits without a fee, contributing significantly to charitable causes. Long divorced, he lived on Benefit Street in Sherman Oaks.
Despite facing health issues in his later years, including a tough bout with COVID-19 in 2020, Dreesen remained optimistic and connected to his roots. Cubs Chairman Tom Ricketts and actor Gary Sinise both honored him after his passing, highlighting his love for family, his Chicago origins, and his charitable heart.
Close friends, including restaurateur Steve Lombardo and former TV and radio executive Larry Wert, remembered Dreesen for his friendly nature, storytelling prowess, and loyalty to his roots.
Dreesen shared a personal story late in life about discovering his real father was Frank Polizzi, who was married to his mother’s sister. Despite this secret, Dreesen held no resentment. His father expressed a regret of not being able to publicly acknowledge Dreesen’s success. A memorial service is planned to honor Tom Dreesen’s exceptional life and contributions.