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If anyone’s been groomed to take on this challenge, it’s Kyle DeSantis. Now 30, he’s the scion of a long-established local showbiz clan. His grandfather and mentor, Tony DeSantis, founded the Drury Lane chain of suburban dinner theaters, and Kyle—raised by his grandparents following the death of his mother—spent his teen years doing everything from selling tickets to managing the catering and convention operations.
In 2005, with Tony and Kyle’s aunt, Diane van Lente, at the helm, Drury Lane opened the Water Tower Place location, offering an ambitious season of original stagings. Their debut show, the musical version of The Full Monty, was a hit, but subsequent productions over the next year were box office disappointments. Meanwhile, both Tony and van Lente were diagnosed with cancer. “It took a toll on everyone,” Kyle recalls. “We couldn’t stay as focused as we wanted to.”
DeSantis has also forged an agreement with Chicago Cabaret Professionals, an organization of local singer-actors, to present a monthly series called Musical Mondays. The deal could attract an off-night audience of fans of classic American popular song.