LOS ANGELES (AP) — Tom Dreesen, who along with partner Tim Reid formed one of America’s first interracial stand-up comedy duos and later spent years as Frank Sinatra’s opening act, died Wednesday. He was 86.

Dreesen died at his home in Los Angeles, according to publicist Lori De Waal. A cause of death was not provided.

After meeting in Chicago, Dreesen and Reid, who was Black, formed “Tim and Tom” in 1969. Against a backdrop of simmering racial tension, they used humor to address social issues and promote understanding between audiences of different backgrounds. They worked together until the mid-1970s.

After splitting with Reid, Dreesen honed a solo comedy act, making over 500 national TV appearances, including 60 visits to “The Tonight Show Starring Johnny Carson.” He also was a frequent guest and sometime guest host on “The Late Show with David Letterman.” Their friendship dated to the early 1970s when both worked at The Comedy Store in West

Hollywood, California.