The Story of Sinatra’s Righthand Man


From shining shoes in Chicago to rubbing elbows with Hollywood greats, this is the story of the one and only Tom Dreesen.

By: Marianna Gatto, ISDA Contributing Editor

Actor and stand-up comedian Tom Dreesen is best remembered as the opening act for Frank Sinatra, a distinction he held for 14 years.

During his 50 years in show business, Dreesen has performed with giants such as Smokey Robinson, Liza Minnelli, Natalie Cole, and Sammy Davis, Jr., and has made over 500 appearances on national television and more than 60 appearances on The Tonight Show.

He was one of David Letterman’s and Johnny Carson’s favorite guests and frequently hosted the show in Letterman’s absence.

But Dreesen’s path to a groundbreaking career in entertainment was anything but traditional.

Born in the working class town of Harvey, Illinois, Dreesen grew up shining shoes in the dark saloons of Chicago’s South Side.

After serving in the Navy and working as an insurance salesman, Dreesen decided to pursue a career in comedy, and went on to share the stage with Tim Reid as America’s first — and only — black and white comedy team.

Dreesen, the boy whose family was too poor to afford a little league uniform, would later throw the ceremonial first pitch at Wrigley Field for the Chicago Cubs on opening day.

Dreesen went from listening to Sinatra sing on the radio to waiting in the wings a few feet away as Ol’ Blue Eyes took the stage.

Dreesen became one of Sinatra’s closest friends and later served as a pallbearer and the emcee at Sinatra’s funeral.

Join the Italian American Museum of Los Angeles and the Italian Sons and Daughters of America for a behind-the-scenes look into the life of a legend of the entertainment industry.

Dreesen will discuss his Italian heritage and invite you to be a fly on the wall for memorable moments with some of the greatest luminaries in entertainment.

The event is free and will be streamed Live on the Italian American Museum of Los Angeles Facebook page on February 18 at 7 p.m. EST and 4 p.m. PST.

Marianna Gatto is the executive director and cofounder of the Italian American Museum of Los Angeles (IAMLA), a historian and author with more than a decade of experience in public history, non-profit leadership, museums, and education.

 

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