Roy Leonard

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Roy Leonard
Roy Leonard

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Roy Leonard worked for WGN Radio as host 1967-1998. He focused on “The World of Entertainment,” featuring movie and theater reviews, contemporary music, and interviews with many of the biggest names in entertainment during the three decades of his program.


“Hello, from Chicago.”

Roy Leonard joined WGN Radio in 1967. During his 31-year career at the station, his radio shows and regular appearances as host and arts critic on television made him one of Chicago’s most popular sources of information and entertainment.

The question most often asked during his career was, “How does he do it?” Roy actually read the book before he interviewed the author. He saw every major movie and play and attended concerts regularly. Such dedication caused personalities such as Sally Field, Quincy Jones, Shirley MacLaine and Charles Kuralt to rate Roy, “the best in his field.” And, many of his radio colleagues remain in awe of Roy’s ability to turn the reading of a script into a friendly chat with his audience.

Roy Leonard
Roy Leonard

An important aspect of “The Roy Leonard Show” was the introduction of new artists. Listeners to WGN Radio were the first to hear such diverse talents as Harry Connick, Jr., Billy Joel, Barry Manilow and Carly Simon. Listeners were also treated to relaxing, in depth conversations with a guest list that reads like an international “Who’s Who” with such stars as Clint Eastwood, Isabella Rossellini, Tom Cruise, Linda Ronstadt, John Cusack, Jimmy Stewart and Ella Fitzgerald.For diversity, Roy frequently took his show on the road with trips to Europe. His program originated from London and Moscow and, in the United States, New York, the Academy Awards in Los Angeles, Disneyland and Walt Disney World.

Roy’s listeners often traveled with him as he and his wife, Shelia, hosted their annual London Theater Tour in October. They also treated their tour members to a food and wine excursion in France, a trip to Norway for the Bergen Music Festival, an Alaskan Cruise, a week in the Netherlands for the 100th anniversary celebration of Vincent Van Gogh and three memorable excursions behind the Iron Curtain before the Soviet coup. At least twice a year, the Leonards offered a New York theater weekend and trips to Canada’s Shaw and Stratford Festivals.

On WGN-TV, Roy’s movie and theater reviews were a regular feature on the Channel Nine News. From October to April of each year, he hosted Family Classics on Sunday afternoons, bringing to the home audience the great films ranging from Robin Hood and Boys Town to The Music Man and Benji. His specials on New Year’s Day garnered great ratings opposite the deluge of football bowl games. In April, 1998, Roy hosted WGN-TV’s 50th Anniversary special.

Roy’s innovative career began in the early fifties at a station in Salem, Massachusetts after attendance at Boston’s Emerson College. His success in the commercial market however, was interrupted by Uncle Sam, and a stint in the United States Air Force found him in Nome, Alaska, at an Armed Forces Radio Station. When his duty expired, Roy returned to radio in Fitchburg, Massachusetts, followed by a job in Framingham MA., as an on-air personality and program director.

It was in Framingham that Roy was asked to appear in a local stage production by the Civic League Players. After passing the casting director’s audition, he asked her for a date and a year later, on October 11, 1953, Sheila Marie Finn became Mrs. Roy Leonard. The first of their six sons, Kip, was born in 1955, and the following year Roy joined WHDH Radio and TV in Boston, where he hosted two daily radio shows and presented the nightly news on television. In 1958, he joined WNAC Radio and TV in Boston as host of the Morning Show on AM radio and anchor on the Early Evening TV News. He also hosted “Yankee Camera,” a Sunday news magazine program on television.

Other Leonard lads arrived in 1956 (Kerry), 1957 (Kolin), 1958 (Kent), 1962 (Kyle), and 1966 (Kelly) and in 1967, along with their six K’s, Shelia and Roy moved to Chicago and the long association with WGN Radio was underway.

After six sons, the Leonards now have eight grandchildren who are frequent visitors to their North Shore home, as all the boys have remained in the Chicago area in such diverse professions as education, architecture, retailing, banking, publishing and theater.

Roy served on the Midwest Board of the American Foundation for the Blind. He is a past President of the Red Cloud Athletic Fund and a board member of the Chicago Film Critics Association. His interest in food and wine led to membership of Les Amis d’Escoffier Society and the Chaine de Rotisseurs.

In 1992, Roy won the prestigious Peter Lisagor Award for Criticism. He also holds a Grammy Award Certificate for his contribution as emcee for the “Tribute To Steve Goodman” and the 1986 Grammy Winning Best Contemporary Folk Recording. From the music industry’s leading trade magazine, Billboard, Roy was honored with Best Feature Radio Programming of the Year for his two hour special with Linda Ronstadt.

As Roy’s radio career neared its end, he hosted a special farewell show from the Museum of Broadcast Communications. A week later, on December, 26, 1998, Roy was joined by Sheila in Studio A for his final regularly scheduled broadcast. But, it was not his final appearance on the station. His Christmas specials have remained a staple of WGN’s holiday line-up. And, in August, 2003, Roy returned to the microphone for part of an afternoon to reminisce with listeners and remind us all of his unique talents.

In October, 1999, Roy was awarded the Lifetime Achievement Award in Radio Broadcasting by the Chicagoland A.I.R. Awards Board of Governors.

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