Stand-up comedian Tom Dreesen, best known as a longtime opening act for Frank Sinatra and as part of an early interracial comedy duo, has died. He was 86. Multiple outlets report that news of his death comes from family representatives and/or his official Facebook page. The reports do not state a cause of death.

Dreesen built a career as a touring comic and television performer, with hundreds of appearances mentioned across outlets. He is also described as having broad appeal within the entertainment industry, with several publications noting he was a favorite of major figures such as Johnny Carson and David Letterman, alongside Sinatra.

Another commonly cited aspect of his legacy is his partnership with Tim Reid. After meeting in Chicago, Dreesen and Reid—who is Black—formed “Tim and Tom” in 1969, one of America’s first interracial stand-up comedy teams. They worked together until the mid-1970s. In later years, Dreesen continued performing and appeared in film and television credits cited by outlets, including “Spaceballs” and “Columbo: Murder in Malibu.”