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Tom Dreesen, the comic who was a close friend of David Letterman and spent years as Frank Sinatra’s opening act, has died.

Tom Dreesen, the standup comedian who warmed up audiences for Frank Sinatra, has died at 86.

Dreesen made his final TV appearance just a week before his death, when he appeared on Byron Allen’s Comics Unleashed, which replaced The Late Show with Stephen Colbert last month.

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Dreesen had served as a mentor figure to Allen–who started his career in standup comedy before becoming a billionaire media mogul–since 1975, according to Variety.

Dreesen’s family announced his death in a Facebook post. “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,” the family wrote. No cause of death has been revealed.

The Chicago-born comic launched his comedy career in the late 1960s with actor and comedian Tim Reid in the groundbreaking duo Tim and Tom, the first biracial stand-up comedy duo in the United States.

Striking out on his own in the mid-1970s, Dreesen opened for the likes of Liza Minnelli, Smokey Robinson, Gladys Knight, and Sammy Davis Jr.

Dreesen began performing alongside Sinatra in 1983 and spent the next 14 years touring as the legendary singer’s opening act, appearing at Sinatra’s final concert in 1995.

“In a lot of ways, he was like a father to me,” Dreesen once said of Sinatra, according to The Hollywood Reporter. “I didn’t have a father that really cared that much where I was and what I did. But Frank would give me advice and counsel and then he was a buddy in a lot of ways. I thought the world of him.”

Over the course of his life, Dreesen made over 500 appearances on national television, according to People, including guest-hosting The Late Show for his friend David Letterman and making frequent appearances on The Tonight Show Starring Johnny Carson.

Letterman, 79, honored Dreesen’s memory in an Instagram post on Wednesday.

“Tom was the first comedian I met at Comedy Store in 1975. We became friends immediately,” he wrote. “He had wisdom and endless stories. Everyone admired him, looked up to him and wondered if he ever stopped talking. He never did, he never will. We love him for that. We’ll miss the stories. God bless you Tom.”

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The official Comics Unleashed Instagram account also paid tribute, writing, “Tom will forever and for always be a cherished part of the Comics Unleashed family. Despite his health struggles, he brought so much joy, life, and vitality to our set: stay tuned for Tom’s last appearance on our show.”

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