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The Untold Story of Tom Dreesen and Frank Sinatra

Tom Dreesen Frank Sinatra are two names that are synonymous with entertainment and showmanship. Both men have made significant contributions to the world of music, comedy, and performance. However, what many people may not know is the deep friendship that existed between these two legends.

In this blog post, we will uncover the untold story of Tom Dreesen and Frank Sinatra and explore the impact of their friendship on both their personal and professional lives. From how they met to the lessons we can learn from their bond, this is a tribute to one of the most iconic friendships in entertainment history.

The Friendship Between Tom Dreesen Frank Sinatra

The friendship between Tom Dreesen and Frank Sinatra began in the late 1960s when Tom was working as a hustler and comedian at a strip club in Chicago. One night, Frank Sinatra walked into the club and Tom was tasked with getting him anything he needed. As fate would have it, Tom’s natural charm and humor caught the attention of Sinatra and the two struck up a conversation.

The Untold Story of Tom Dreesen and Frank Sinatra

From that moment on, a special bond was formed between the two men. It wasn’t just about business or entertainment, but a genuine friendship based on mutual respect, admiration, and laughter. Despite their different backgrounds and lifestyles, Tom and Frank found common ground in their love for performing and making people laugh.

How Tom Dreesen Became Friends with Frank Sinatra

For Tom Dreesen, becoming friends with Frank Sinatra was like a dream come true. Growing up in a working-class family in Harvey, Illinois, Tom had always admired Sinatra from afar. He would listen to his records and watch his movies, dreaming of one day meeting the man himself.

The Untold Story of Tom Dreesen and Frank Sinatra

Tom’s journey to becoming friends with Frank Sinatra was filled with persistence, hard work, and a little bit of luck. After serving in the United States Navy, Tom returned to Chicago and started working as a comedian. He would often perform at strip clubs and bars, trying to make a name for himself in the entertainment industry.

When Frank Sinatra walked into the club where Tom was performing, it was a defining moment in his career. Not only did he impress Sinatra with his comedy, but he also showed his dedication and loyalty by getting him anything he needed. This caught Sinatra’s attention and led to their infamous conversation and the start of a lifelong friendship.

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The Impact of Frank Sinatra on Tom Dreesen’s Career

Tom Dreesen’s friendship with Frank Sinatra had a significant impact on his career in entertainment. As a struggling comedian, Tom saw first-hand the level of success and talent that Sinatra possessed. He learned valuable lessons from Sinatra about stage presence, delivery, and connecting with an audience.

Frank Sinatra also opened doors for Tom in the entertainment industry. He invited Tom to join him on tours, perform at his shows, and even appear on his television specials. This exposure helped Tom gain recognition and establish himself as a respected comedian.

The Untold Story of Tom Dreesen and Frank Sinatra

Moreover, Tom’s friendship with Frank Sinatra gave him an opportunity to perform in front of diverse audiences and travel the world. He shared the stage with some of the biggest names in show business, including Sammy Davis Jr., Dean Martin, and Liza Minnelli. This experience not only elevated Tom’s career but also allowed him to learn from some of the best entertainers in the world.

Tom Dreesen’s Memories of Working with Frank Sinatra

Tom Dreesen has countless memories of working with Frank Sinatra, many of which he shares in his book “Still Standing: My Journey from Streets and Saloons to the Stage and Sinatra.” In the book, Tom recounts humorous and heartwarming stories of their time together, giving readers a glimpse into their special friendship.

One particular memory that stands out is when Tom and Sinatra had dinner with Prince Charles and Princess Diana in London. Tom was asked to say grace before the meal, and he took this opportunity to make a joke about Sinatra’s infamous temper. To Tom’s surprise, Princess Diana laughed so hard that she had tears in her eyes. This moment not only showed the power of humor but also the bond between Tom and Frank.

Another memorable experience for Tom was when he opened for Sinatra’s concert at Carnegie Hall in 1986. This was a huge honor for Tom, as Carnegie Hall is considered one of the most prestigious venues in the world. As always, Tom delivered a stellar performance, and Sinatra gave him a standing ovation, showing his support and pride for his friend.

The Humorous Side of Tom Dreesen and Frank Sinatra’s Friendship

One of the things that made Tom and Frank’s friendship so special was their shared love of humor. Both men were known for their quick wit and ability to make people laugh, and their friendship was no different. They often joked around and pulled pranks on each other, never taking themselves too seriously.

In Tom’s book, he shares a funny story of how he once made Sinatra believe that he had an illegitimate son. Tom received a letter from a woman claiming that Sinatra was the father of her child, and Tom decided to have some fun with it. He invited the woman to a show where he introduced her to Sinatra as his “son.” It wasn’t until the end of the night that Tom revealed the truth, much to Sinatra’s relief and amusement.

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The Untold Story of Tom Dreesen and Frank Sinatra

Their humor extended beyond just jokes and pranks. Tom and Frank would often have deep conversations filled with laughter and witty banter. They would also attend events together, such as the Friars’ Club roasts, where they would roast and tease each other in good spirits. Their friendship was a perfect balance of humor and heart, making it one that many envied.

Lessons Learned from Tom Dreesen and Frank Sinatra’s Friendship

The friendship between Tom Dreesen and Frank Sinatra teaches us valuable lessons about loyalty, hard work, and the power of humor. One of the main lessons we can learn is the importance of being persistent and taking every opportunity that comes our way. Tom’s persistence in pursuing his dream ultimately led to his friendship with Sinatra, which played a significant role in his career success.

Their friendship also shows us the impact that a mentor can have on someone’s life. Tom credits much of his success to the lessons he learned from Frank Sinatra and the opportunities he was given through their friendship. In turn, he has passed down those lessons and opportunities to the next generation of entertainers, paying it forward as a mentor to aspiring comedians.

Tom Dreesen’s Tribute to Frank Sinatra

Tom Dreesen’s admiration for Frank Sinatra goes beyond just their friendship. He sees Sinatra as an icon and a legend in the world of entertainment, and he pays tribute to him in various ways. One notable tribute is Tom’s one-man show, “An Evening of Laughter and Memories of Sinatra.” In this show, Tom shares stories, jokes, and memories of his time with Sinatra, giving audiences an inside look into their friendship.

Tom also wrote and performed a song called “The Good Times” in honor of Sinatra after his passing in 1998. This touching tribute highlights the good times they shared and the impact Sinatra had on Tom’s life. The song has become a popular tribute to Sinatra and is often played at events and celebrations in his memory.

The Untold Story of Tom Dreesen and Frank Sinatra

The Legacy of Tom Dreesen and Frank Sinatra’s Friendship

The friendship between Tom Dreesen and Frank Sinatra will forever remain a significant part of entertainment history. Their bond showed that despite differences in age, background, and lifestyle, two people can form a genuine and lasting friendship. Their friendship also paved the way for future generations of entertainers to collaborate and support each other, proving that there is room for everyone to shine in the spotlight.

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Their legacy lives on through the memories, stories, and lessons that continue to be shared by Tom and others who knew them. Their impact on the world of entertainment will never be forgotten, and their friendship will always be celebrated.

Behind the Scenes of Tom Dreesen and Frank Sinatra’s Friendship

Behind the glamorous stage performances and public appearances, Tom and Frank’s friendship was built on a strong foundation of trust, loyalty, and mutual respect. They supported each other through difficult times, celebrated each other’s successes, and always had each other’s back.

In his book, Tom shares that Frank would often call him at 2 or 3 in the morning just to talk about anything and everything. This showed the deep level of trust and friendship between the two men, as well as their genuine interest in each other’s lives.

The Untold Story of Tom Dreesen and Frank Sinatra

Moreover, Tom and Frank’s friendship was not just limited to the entertainment industry. They would often spend time together outside of work, whether it was golfing, attending sporting events, or having dinner. This goes to show that their friendship was not just based on business, but also on a genuine bond between two individuals.

The Lasting Bond Between Tom Dreesen and Frank Sinatra

Despite Frank Sinatra’s passing in 1998, his friendship with Tom Dreesen has remained strong. Tom continues to honor Frank’s memory through his performances, tributes, and stories, keeping their bond alive. He also pays tribute to Sinatra by giving back to the community through his charity work, inspired by Sinatra’s own philanthropic efforts.

Tom also remains in touch with the Sinatra family, particularly Frank’s daughter, Nancy Sinatra. She has expressed her admiration for Tom and his friendship with her father, saying that Tom “showed him love and respect and laughter.” Their friendship continues to inspire others and serves as a reminder of the enduring power of true friendship.


The friendship between Tom Dreesen and Frank Sinatra is one that will forever be remembered in the world of entertainment. It goes beyond just business or professional success, but rather a genuine bond between two individuals who shared a love for performing and making people laugh. Their friendship not only impacted their own lives but also the lives of those around them, leaving a lasting legacy that will continue to inspire generations to come.

The Untold Story of Tom Dreesen and Frank Sinatra

As Tom himself said, “When you talk about Frank Sinatra, you have to talk about his voice, his acting, and his style. But if you want to know who Frank really was, you have to talk about his heart. And I was lucky enough to see it up close.”

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