Tom Dreesen, the classy comedian who opened for Frank Sinatra for 14 years, pushed for stand-ups to get paid at The Comedy Store and partnered in a pioneering interracial act with Tim Reid, has died, his family and representatives announced Wednesday. He was 86.

The pride of Chicago, Dreesen made hundreds of TV appearances during his 50-plus years in show business, including dozens on The Tonight Show Starring Johnny Carson and on the late-night programs hosted by David Letterman, his dear friend from their days in the 1970s at The Comedy Store in West Hollywood.

Always thought-provoking but never controversial, few were better at delivering a joke.

“I don’t know if you know this or not, but in 1871 in baseball, men started wearing the cup to protect the family jewels,” Dreesen quipped during a gig at the Laugh Factory. “In 1971, it became mandatory to wear a helmet. It took men 100 years to realize the brain is important also.”

After warming up audiences for the likes of Liza Minnelli, Smokey Robinson, Gladys Knight and Sammy Davis Jr., the always dapper Dreesen began sharing a bill with Sinatra in 1983 and shared a special camaraderie with the Chairman of the Board during the singer’s twilight years.