The Life and Legacy of Tom Dreesen

Tom Dreesen, a distinguished comedian, left an indelible mark on the entertainment industry over the years. Originally from Harvey, Illinois, Dreesen achieved a stellar career with over 500 TV appearances, including 61 times on “The Tonight Show.” His significant roles included being the opening act for legends such as Smokey Robinson, Tony Orlando, Gladys Knight, Liza Minnelli, Sammy Davis Jr., and Frank Sinatra. Dreesen served as Sinatra’s opening act for 13 years and was notably present at Sinatra’s wake and funeral.

Upon his death at 86, many remembered him fondly. David Letterman described him as both a natural storyteller and a person with a good heart. Dreesen’s life story is a testament to resilience and dedication.

Early Life and Challenges

Born on September 11, 1939, Dreesen faced numerous hardships as the third of eight children. His upbringing was challenging, marked by financial difficulties and his parents’ struggles with alcoholism. Despite these challenges, Dreesen showed resilience. In his early years, he worked various jobs, including caddying and shining shoes. He didn’t complete high school but made a pivotal decision to join the Navy, which opened new opportunities for him.

Beginning of a Comedy Career

Dreesen’s comedic journey began in earnest after his time in the Navy. He joined the Jaycees and collaborated with Tim Reid to form one of the first interracial comedy duos, Tim & Tom. Despite the absence of comedy clubs at the time, their act found venues across Chicago, such as Mister Kelly’s and the Playboy Clubs.

The duo disbanded in 1974, leading Dreesen to pursue a solo career in Los Angeles. He endured tough times initially, living in an abandoned car and surviving on minimal earnings.

Rising to Fame

Determined and persistent, Dreesen became a regular at the Comedy Store. He built a reputation among other future stars like David Letterman, Jay Leno, and Robin Williams. With time, he managed to secure television spots and make his mark in the comedy circuit.

His pivotal break came with his performance on “The Tonight Show,” earning widespread acclaim. Subsequently, Dreesen found himself entertaining audiences nationwide, opening for big names and enjoying successful stints in Las Vegas.

Time with Sinatra

Among the highlights of his career was Dreesen’s long-standing association with Frank Sinatra. Joining Sinatra as his opening act exposed Dreesen to a world brimming with stars and memorable moments. He formed strong bonds with many celebrities and cherished his time with Sinatra.

A Life of Giving

Beyond show business, Dreesen was recognized for his charitable endeavors. His efforts were extensive, and he contributed more to charity through benefit performances than most entertainers. Even in later years, Dreesen remained optimistic despite health challenges, continuing to engage with fans.

Tributes and Reflection

Tom Dreesen’s passing evoked heartfelt tributes from both friends and public figures. Tom Ricketts, Cubs chairman, praised Dreesen’s lasting connection to his roots and his unwavering love for Chicago. Similarly, Gary Sinise and Steve Lombardo reflected on Dreesen’s friendship, kindness, and dedication to others.

Dreesen’s family plans to hold a memorial service to honor his memory, celebrating the life of a man who, despite personal struggles, left a legacy of laughter and generosity.