Tom Dreesen dies at 86 after 13 years with Sinatra

Comedian Tom Dreesen, who grew up in Harvey and toured with Frank Sinatra for 13 years, died Wednesday at 5:50 a.m. at age 86. His children posted that he wanted people to know how much joy they brought him.

Comedian Tom Dreesen spent 13 years on the road as an opening act for Frank Sinatra, but the story of how he got there started much closer to home—seven siblings behind him, one family struggling to make ends meet in Harvey.

Dreesen died Wednesday at 5:50 this morning, according to a post from his children on his Facebook account. The message said: “My sister and I regret to inform you that our father passed away at 5:50 this morning. He wanted you all to know how much joy you brought him through the years. He said to tell you that he loved you all. May he rest in peace.”.

He was 86.

Born into a Catholic family of eight children. Dreesen grew up in a neighborhood where his family was one of the only white families in a Black community. Needing to help support his seven siblings. he worked wherever he could—setting pins in bowling alleys. shining shoes in taverns and selling newspapers on street corners—jobs he leaned on to keep food on the table and to keep the family going.

After serving four years in the military, beginning when he was 17, he took on an array of construction and other hard manual labor jobs. Comedy came later, and once it did, he treated it like something that could not be taken away.

Dreesen first found a foothold in the comedy world alongside comedian Tim Reid—later known for his acting—forming the duo Tim & Tom. Reid is Black, and the pair became one of the nation’s early multiracial comedy acts.

Dreesen and Reid met in 1969 through the South Side Jaycees, a civic and business leadership organization for young professionals. At the time, Dreesen was selling insurance and Reid was a salesman for a chemical company. The duo also gave a drug education presentation for kids. which drew enough attention that people urged them to go professional.

When Reid left to work on his own, Dreesen—already a husband with three kids—felt pressure to quit comedy for steadier work. Still, he refused to let it stop him.

A breakthrough came when he filled in at the last minute for a comedian who canceled an opening gig for Sammy Davis Jr. The Rat Packer took Dreesen on the road, and that momentum carried into a long run with Sinatra. He later worked for 13 years as an opening act for Frank Sinatra.

In the decades that followed, Dreesen became a familiar presence across late-night television, making more than 500 TV talk-show appearances. He was a favorite of late-night stars Johnny Carson and David Letterman.

He also helped shape others behind the scenes. Early in their stand-up careers, Dreesen mentored David Letterman and Jay Leno at the Comedy Store in Los Angeles. He became a motivational speaker and aided countless other comedians trying to break into the business.

His commitment to performers extended beyond advice. In 1979, he helped lead a comedians strike at the Comedy Store to fight for compensation for the comedians who performed there.

Even after making Los Angeles his home in 1974, he continued to return to Chicago often. In 2003. at age 84. he spent two weeks in the Chicago area performing his one-man show “The Man Who Made Sinatra Laugh.” During that stay. he threw out the first pitch at a Cubs game and sang “Take Me Out to the Ball Game”—an honor he received more times than any other comedian.

Dreesen attended Thornton Township High School and was known for pushing himself to help charitable causes, including raising money for his alma mater. An avid golfer, he hosted the Tom Dreesen Celebrity Invitational featuring Chicago celebrities including Mike Ditka and Jim McMahon.

He drew on his childhood experiences for his routines, including releasing a stand-up comedy album in 1989 titled “That White Boy’s Crazy,” recorded live in Harvey before a Black audience.

His connections in Chicago entertainment remained strong as his career grew. He was friends with Gary Sinise, Joe Mantegna, Dennis Franz and Bill Petersen. In a Facebook post. Sinise wrote: “This morning America lost one of our great comedians and patriots. and I lost a dear friend. Tom Dreesen died at 86 years old. He was a special person, a U.S. Navy veteran with a tremendously charitable heart. “Tom was hilarious, always could make us laugh and such a good friend. I will miss him terribly. What a great long career he had in show business.”.

For many younger performers, the help Dreesen offered was personal as well as practical. Comedian Roger Rose. who got a boost from Dreesen when he was a teen attending New Trier High School. remembered it this way: “He would help anyone looking to get into comedy or get better at comedy and make it in comedy any way he could. ” Rose said. “I met Tom when I was 15 and interning at WFLD Channel-32. and I told him I wanted to get into comedy. and he gave me his number and told me to call him if I was ever in Los Angeles.” Rose said he kept in touch with him ever since.

The arc of Dreesen’s life moved from making money with his hands and his hustle in Harvey to building a national career defined by laughter—and then. just as importantly. by making room for others to follow. When he died Wednesday. his family’s message framed the final note as something he felt rather than something he performed: the joy people brought him through the years. and the love he asked to be passed along.

Tom Dreesen Frank Sinatra Harvey Illinois Comedy Store David Letterman Jay Leno Tim Reid Gary Sinise Joe Mantegna Dennis Franz Mike Ditka Jim McMahon