Longtime Chicago radio and TV personality Roy Leonard, who introduced listeners and viewers to some of America’s biggest celebrities as they were just getting started, has died. He was 83.
Leonard was well known around the Midwest for his decades of talk radio, celebrity interviews and movie reviews on Chicago’s WGN Radio and TV, where he crafted an improvisational interview style around the art of listening and allowing a conversation to unfold.
“He always read the book before he saw the movie; he did his research, and then he let a conversation happen. He didn’t try to pre-plan everything,” said his son, Kelly Leonard.
Leonard died Thursday night at Evanston Hospital, north of Chicago, surrounded by his six sons, their wives and several of his grandchildren, Kelly Leonard said.
Leonard’s three-decade run at WGN was marked by interviews with an array of entertainers, ranging from the mime Marcel Marceau to Tom Cruise.
He caught many of them as they were just starting out, talking on location with Christopher Reeve about Superman and Dustin Hoffman about making Tootsie in 1982.
Kelly Leonard, executive vice president of comedy group The Second City, said his family’s dinner table often resembled his dad’s radio show, with discussions of music, politics and culture and occasional appearances by musicians and other entertainers themselves.
Leonard was born in Redwood, Minnesota. He came from nothing, though he didn’t dwell on growing up poor, Kelly Leonard said.
According to his son, Leonard ran away from home at 16 and ended up on the streets of Boston, where he was taken in by a woman who hired him to walk her dog and helped him through college.
He did some sports play-by-play and landed radio gigs. By 1967, he arrived at WGN, where he was reaching audiences around the Midwest. In 1985, he took over hosting the long-running show Family Classics, which aired films on TV.
Leonard had been in the hospital for several weeks with respiratory and other health problems, his son said. When it became clear he would soon pass away, Leonard’s family gathered around him, listening to one of his favorite jazz artists, Dave Brubeck, on an iPad and waiting for a priest to give him last rites.
“Literally at the end of the prayer, my dad went,” Kelly Leonard said. “He always knew how to sign off. His timing was perfect.”