Singing senior: William Conroy will celebrate his 90th birthday next month at Mills Tower in Oak Park.MARTY STEMPNIAK/Staff

In another era, William Conroy used to hop on the el in Oak Park and ride to Michigan Avenue in the city. There he had a singing job on a radio show called The Chicago Theatre of the Air in the 1940s and was pulling in more than $50,000 for his work, no small sum in that era, not too far removed from the Great Depression.

“Live radio in Chicago was a very lucrative field until TV came along and knocked it out,” he said.

Fast forward some 70 years later, and Conroy is long retired from his career of crooning. He lives in the Mills Park Tower retirement community in Oak Park, and next month, he’ll celebrate his 90th birthday.

Conroy said he first got interested in singing in the late 1930s, taking private lessons at the Chicago Conservatory of Music. He got his first big break around 1943, when he started performing for the Municipal Theater Association of St. Louis, where he sang for two seasons. He starred in shows such as Naughty Marietta, about a French princess who flees to New Orleans to avoid a prearranged marriage, as well as Robin Hood, in which he played the title character.

After building a name for himself, Conroy returned to his hometown of Chicago, scoring a gig on WGN Radio, as well as performing the occasional show at venues such as Grant Park in 1946 and “The Messiah” at Orchestra Hall in 1956.

“It was quite lucrative for those times, and when you’re doing something you love, it’s not like working,” Conroy said.

While taking part in the opera La Traviata at the 8th Street Theatre, he crossed paths with some famous faces. Future broadcasting legends Barbara Walters and Hugh Downs performed in the chorus in 1946, according to the program, though Conroy said he never got a chance to meet them.

With the end of radio’s heyday and his skills diminishing, Conroy decided to call it quits in the early 1970s, after spending the previous decades teaching choir at St. Catherine of Siena. He’s been retired for the past 40 years, annually visiting his sister in the Canary Islands for six months each year. He stopped, though, a few years back, after getting a nasty case of double pneumonia.

Nowadays, Conroy keeps busy trying to figure out “this computer thing.” And he’s always socializing, cracking jokes and just being “the life of the party” at Mills Park Tower, according to Melissa Winn, manager of Mills Park Tower.

Conroy got married in the 1940s, had three children and later divorced. His daughter, Valerie Gager, 66, recently moved into Mills Park Tower, too, about a year ago. Her dad doesn’t sing anymore, but she remembers him harmonizing with her as a child.

“He’s almost 90, so he doesn’t have much of a voice, but it lasted a good long time,” she said. “It was a beautiful voice from what I remember growing up.”

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