Tom Dreesen, the trailblazing stand-up comedian and actor who spent more than five decades making audiences laugh, has died at the age of 86. The veteran performer, best known to many as Frank Sinatra’s longtime opening act and as one half of the groundbreaking comedy duo Tim and Tom, died on Wednesday, June 17, at his home in Los Angeles. No cause of death was given.

Dreesen’s family shared the news in a statement obtained by PEOPLE. “For more than five decades, Tom Dreesen brought laughter, heart, and humanity to audiences across America. A proud native of Harvey, Illinois, Tom built a remarkable career through perseverance, talent,” they wrote. In a separate message posted to his official Facebook page, his children wrote that their father passed away early in the morning, adding that he wanted audiences to know how much joy they had brought him over the years.

Born on Sept. 11, 1939, Dreesen grew up in Harvey, a south suburb of Chicago, as the third child in a poor family of eight. He began working at a young age, selling newspapers, shining shoes and setting pins in bowling alleys to help make ends meet. He attended Thornton Township High School but dropped out as a sophomore, and at 17 he enlisted in the U.S. Navy, leaving the service in 1960.

After his time in the Navy, Dreesen returned to the Chicago area and worked a series of jobs, including selling insurance. It was during this period that he met Tim Reid, the future “WKRP in Cincinnati” star, and the two formed a comedy team that would help break new ground in American entertainment.

A Groundbreaking Duo

Dreesen and Reid formed “Tim and Tom” in 1969, becoming one of the first interracial comedy duos in the United States. “Together, they became one of America’s first interracial comedy duos, using humor to break barriers and open doors during a time of great social change,” the family statement read.

The partnership left a lasting impression on the comedy world. Years later, Dreesen and Reid co-wrote the 2008 book “Tim and Tom: An American Comedy Act in Black and White,” chronicling their experience performing together during a turbulent era. After the duo split, Dreesen built a solo career that would carry him to the heights of show business.

A Fixture on Late-Night Television

As a solo act, Dreesen became a familiar face on national television, racking up more than 500 appearances over the course of his career. He made roughly 60 visits to The Tonight Show Starring Johnny Carson, establishing himself as one of the most reliable stand-ups of his generation.

He was also a frequent guest, and occasional guest host, on The Late Show with David Letterman. His friendship with Letterman dated back to the early 1970s, when both performed at The Comedy Store in West Hollywood. “He had wisdom and endless stories. Everyone admired him, looked up to him,” Letterman wrote in a tribute. Dreesen’s final television appearance came just last week on “Comics Unleashed with Byron Allen.”

Sinatra’s Right-Hand Man

Dreesen warmed up audiences for some of the biggest names in entertainment, including Liza Minnelli, Smokey Robinson, Gladys Knight and Sammy Davis Jr. In 1983, he began sharing a bill with Frank Sinatra, launching a partnership that would last 14 years and define much of his legacy. The two grew close, and Dreesen served as a pallbearer and spoke at Sinatra’s funeral after the singer died in 1998.

Beyond stand-up, Dreesen built a steady career as a character actor. His film credits included “Spaceballs,” “Man on the Moon” and “Trouble With the Curve,” along with the HBO movies “The Rat Pack” and “Lansky.” On television, he appeared in series such as “Columbo,” “Murder, She Wrote” and “Touched by an Angel.”

Dreesen was also remembered as an advocate for his fellow performers. Drawing on his roots as a Chicago teamster, he helped organize a 1979 strike at The Comedy Store to ensure that comedians were paid for their work. In his later years, he devoted himself to charitable causes, motivational speaking, and veterans’ work, serving as an ambassador for the Gary Sinise Foundation. “America lost one of our great comedians and patriots, and I lost a dear friend,” Sinise wrote following news of his death.