New book explores comedian and Harvey native Tom Dreesen’s unlikely success

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Despite humble origins in the south suburbs, the famed comedian has been heralded in Hollywood and across the nation

By Carrie Steinweg

LANSING, Ill. (February 25, 2021) – There once was a little boy who came from a poor family in a poor neighborhood but grew up to travel the country as an entertainer. It sounds like a fairy tale.

From shoe shining to Sinatra

That same little “dirt-poor young kid” went to Cubs games as a young child with nuns from the local church. He would later lead a crowd in the singing of the 7th Inning Stretch from the team’s press box at Wrigley Field on a regular basis.

That boy once stood on a corner selling newspapers as he watched a parade go by in his hometown of Harvey, Illinois, on Lou Boudreau Day (a baseball player, manager, and broadcaster who also hailed from Harvey). He was later welcomed warmly back to the area when a street was named after him, and he was introduced to the crowd by Boudreau.

That same kid worked in taverns shining shoes at age eight while Frank Sinatra played on the juke box. He would later share a stage with Sinatra (as his opening act, no less), fly on Sinatra’s private jet, and serve as a pall bearer at his funeral.

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Tom Dreesen (right) poses with Frank Sinatra. (Photo from TomDreesen.com)

Collecting memories of a remarkable life

That little boy is Tom Dreesen, now of California. Dreesen is a comedian, actor, military veteran, motivational speaker, talk show host, mentor, charity performer, golfer, singer of “Take Me Out to the Ballgame,” and now, author.

If there was ever a poster boy for a “full circle moment,” it would be Dreesen. He has a lifetime of remarkable stories to tell. Despite being born to two alcoholic parents and growing up with seven siblings in a shack the size of a railroad car without a shower or bathtub, he worked hard to make his way to Hollywood. His decades-long career has included working with such names as Sammy Davis, Jr., David Letterman, and Frank Sinatra, with whom he worked for 13 years.

Now, the 81-year-old has released a book about his experiences.

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Tom Dreesen’s book, “Still Standing: My Journey from Street and Saloons to the Stage and Sinatra” came out in the summer of 2020. (Image from TomDreesen.com)

“The reason for the book is that ever since I started out in showbiz starting back with the ‘Tim & Tom’ show with Tim Reid and touring the nation, anytime anything poignant or funny would happen, I would journal and write it down. I was thinking, ‘This is funny, maybe one day I’ll want to tell this to my kids or grandkids,’” Dreesen said. “And then with the team breaking up and going to the west coast and struggling out there, and in that struggle I went through with all the rejections, I would journal those poignant moments and some of the fun moments.”

The struggles started to subside when Dreesen made his first appearance on “The Tonight Show” with Johnny Carson. “That was life-changing,” he said. “I journaled some of that and of my touring with Sammy Davis, Jr., and Smokey Robinson, and then finally with Sinatra. I began to collect all these stories, and so I remembered them years later and kept them in a binder.”

His impressive entertainment career has spanned more than five decades with over 500 appearances on national television as a stand-up comedian, including more than 60 on “The Tonight Show.” He was one of David Letterman’s favorite guests and frequently hosted the show in Letterman’s absence.

Binder to Book

In recent years as he revisited the stories in that binder, he thought, “Maybe one day my grandchildren’s children who didn’t know me would wonder what I was like, and then I could have this book for them to read.”

The book had been in the works for some time. It was mostly complete before a serious surgery in February 2019 provided Dreesen with material for the book’s final chapter. It was last fall, during the pandemic, that his book, Still Standing: My Journey from Streets and Saloons to the Stage and Sinatra, was released. The book includes a foreword by David Letterman.

“Pinch-me” moments

One of the most poignant stories of Dreesen’s life began in 1948. “All the horns were blowing and cars were coming from everywhere, and I was on a corner selling the Harvey Tribune, and I asked one of the elders what was going on, and he said, ‘It’s Lou Boudreau day, son,’” Dreesen recalled.

Boudreau, from Harvey, most notably played shortstop for the Cleveland Indians while managing the team, a dual role more common in the early and mid 20th century. In 1948, he guided Cleveland to a World Series title.

“Everyone was all excited, and there was a big parade,” Dreesen said, “and I saw him come out of the Elk’s Club and talk to people and then go down to Thornton High School where he was going to sign autographs. That’s the day I walked away thinking, ‘Wow someone from Harvey is famous!’”

Dreesen doubted if such a rags-to-riches fate awaited him, however. “I would fantasize, like little boys do, that maybe one day they would do that for me,” said Dreesen.

On August 22, 1992, Dreesen returned to Harvey when a street was named in his honor.

Over the years he has given his time and talents for charity events, one being a celebrity golf tour with showbiz personalities and athletes from a number of sports. “It was people that were a ten handicap or below. I’m playing with Johnny Bench, Mike Schmit, Mario Lemieux, John Elway, Dan Marino, Michael Jordan. There were 42 hall-of-famers, and I’m playing against them,” said Dreesen. “If you told me when I was a little boy, ‘One day you’re going to get into an arena and you’re going to compete with the greatest athletes that ever lived in your lifetime,’ I’d say no, that can’t happen. But I was doing that. My whole life is ‘pinch-me moments.’”

“Tell them you’re from Harvey”

When individuals who grew up in the Chicago suburbs are asked where they are from, they’ll often answer with “Chicago,” since it is larger and more recognizable. Dreesen has always emphasized that he is from Harvey, and legendary entertainer Jack Benny had something to do with that.

“Jack Benny told me many years ago, ‘Tom, when you first go on ‘The Tonight Show,’ tell them you’re from Harvey, Illinois. Tell them about you and growing up in Harvey. You could say Chicago—it’s more metropolitan, but there are more Harveys out there than there are Chicagos,’” Dreesen explained.

Benny said to him “Where am I from, Tom?”

Dreesen quickly responded, “You’re from Waukegan.”

“How’d you know that?” Benny asked.

“Well I heard you say it so many times,” Dreesen replied.

Benny then said, “That’s right. I’m the only comedian to come from Waukegan, Illinois, and you’re the only comedian I ever heard of from Harvey, Illinois.”

Each season for many years, Dreesen has returned to Chicago to continue a tradition that the famous broadcaster Harry Caray epitomized: the 7th Inning Stretch. After Caray’s death, the Chicago Cubs organization began inviting different celebrities in to lead “Take Me Out To The Ballgame” in the middle of the 7th inning at Cubs home games. Dreesen and actor Joe Mantegna, a Chicago native, are tied for the most times singing the stretch since Caray’s death.

Dreesen gives back

Whether it’s been playing a celebrity golf event for a special cause or doing a performance for charity, Dreesen has found a number of ways to give back. One of his charitable efforts has been spending Thanksgiving and Christmas serving food to the homeless at the Laugh Factory Comedy Club in Los Angeles.

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Dreesen (left) and comedian Tiffany Haddish at The Laugh Factory in November of 2020. Dreesen has been serving Thanksgiving meals there for 40 years. (Photo from Tom Dreesen’s Facebook page)

For years, he also volunteered mentoring inner-city kids at a “Comedy Camp” at the Laugh Factory. “The kids would get lunch and an opportunity to get up on stage and say anything they wanted, and we comedians would tutor the ones who would like to become stand-up comedians, but encourage those who didn’t to stand up and tell us their story,” Dreesen said. “Sometimes they would tell us stories about their life that were very funny, and sometimes you’d gasp and choke up when you’d hear what they had been through.”

One of those heartbreaking stories came from a young girl who shared a story that brought Dreesen to tears. That girl was Tiffany Haddish, now a successful comedian and actress. The two still see each other when they go to the Laugh Factory to feed the homeless.

Lansing connections

In 2014, Dreesen was in Lansing filming scenes for a pilot called “Cowl Girl” at the Lansing Municipal Airport. The pilot was produced by Lansing resident Michael Sanow, who has been friends with Dreesen for the past 30 years. The two met at a show at South Suburban College where Dreesen’s doo-wop group was an opening act.

“What can I say about Tommy? He’s one of the kindest people I’ve ever met,” said Sanow. “Sure, he’s funny, but he epitomizes class. He’s just an all-around great guy and always a joy to be around or talk with, whether we’re working or not. I’m proud to call him my friend, and [I’m] jealous, honestly, that he looks better at 80 years old than I do at 49.”

Reading Dreesen’s book

Dreesen said that because of the pandemic, he was unable to do a traditional book tour but has done several Zoom events with bookstores. Interested readers can order his book online at TomDreesen.com, Amazon.com, SimonandSchuster.com, and BarnesandNoble.com.

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