Tom Dreesen, the stand-up comedian and actor known for his long run as Frank Sinatra’s opening act, has died at 86.

His family confirmed his death, marking the end of a career that stretched across comedy clubs, television, film, and major concert stages. Dreesen became widely known for touring with Sinatra for 14 years, a role that placed him in front of large audiences and built a close professional bond with the singer.

Before that chapter, Dreesen made history with actor and comedian Tim Reid as part of Tim and Tom, one of the first interracial comedy duos in the United States. Their act used humor to address race and everyday life during a period when that kind of pairing was rare onstage.

Dreesen also appeared on late-night television and worked steadily as a solo comic for decades. Beyond entertainment, he supported charitable causes and often spoke about his working-class upbringing.

His career leaves a lasting mark on American comedy and live entertainment.