Jeremy Piven spends a lot of time on the road doing stand-up comedy at comedy clubs all over the world. Sometimes Piven gets to work with the best comedians in the business.
On the latest episode of How U Livin J Piven, comedian Tom Dreesen discusses having more than 60 appearances on The Tonight Show and touring with Sinatra for over a decade. In the last episode of 2021, Tom teaches Jeremy a lifetime’s worth of showbiz knowledge.
Tom Dreesen has been in show business for 50 years. Along the way, Tom has made over 500 appearances on national television as a stand-up comedian, including more than 60 appearances on The Tonight Show. He was one of David Letterman’s favorite guests and frequently hosted the show in Letterman’s absence. He also appeared countless times in Las Vegas, Tahoe, Reno, and Atlantic City with artists like Smokey Robinson, Liza Minnelli, and Sammy Davis, Jr. And, for 13 years, he toured the nation as the opening act for Frank Sinatra. A career like this is rich in stories, and no one tells them better than Tom does.
In 1979 he supported the strike at The Comedy Store in West Hollywood. The strike was settled and the comedians performing there began to get paid; that year, he also appeared on Beat The Clock. In 1989, Dreesen released a comedy album through Flying Fish Records called That White Boy’s Crazy. The album was recorded in front of an all-black audience in Harvey, Illinois.
In 2008, Dreesen, Reid, and former Chicago Sun-Times sportswriter Ron Rapoport collaborated on the book Tim and Tom: An American Comedy in Black and White.
On June 9, 2020, Post Hill Press published Dreesen’s memoir, Still Standing…My Journey from Streets and Saloons to the Stage, and Sinatra.
Tom Dreesen is performing his one-man show, The Man Who Made Sinatra Laugh, throughout the country and via live stream, and he’s receiving rave reviews from coast to coast.
