Kyle DeSantis

The Drury Lane Theatre Water Tower Place is in a tricky situation. A 549-seat commercial venue in an expensive neighborhood better known for shopping than for entertainment, it’s competing with the huge Broadway-style houses in the nearby Loop theater district on the one hand and the small to midsize nonprofit theaters that dominate the rest of the city on the other. Tucked away on Chestnut east of Michigan Avenue, it’s easily overlooked by folks shopping the Magnificent Mile. And because it has alternated between self-produced shows and rentals since it opened three years ago, it hasn’t been able to establish a distinctive identity.

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.”

Drury Lane Water Tower Place became a rental house. Broadway in Chicago’s 2006 production of The 25th Annual Putnam County Spelling Bee ran there for a year and a half; 2007 brought productions of two musicals, Altar Boyz and Shout!, that fared less well.

Kyle took charge of the business a year ago, following the deaths of his grandfather and aunt. Under him, Drury Lane Oakbrook Terrace (the only other theater left in the downsized chain) had the biggest hits in its 24-year history—the musical bio Buddy: The Buddy Holly Story and Meet Me in St. Louis, a stage version of the 1944 MGM classic. Now he’s focusing on the Water Tower Place location.

“If I’m in charge of the product I can control the quality,” he says. His plan: to transfer Buddy and Meet Me in St. Louis to Water Tower Place and see if city audiences respond as enthusiastically as suburban theatergoers did. “We’re taking the two shows that were so successful in Oakbrook Terrace and bringing them downtown to see if they have a life here,” says DeSantis, who lives in Streeterville. “I want to see if we can get back into producing shows downtown again.”

With its score of golden oldies, the Drury Lane Buddy won praise for its period authenticity the first time around. “It was important that we make the show realistic and youthful,” says DeSantis. “The cast is young, and the actors play their own instruments. Not only that, the instruments themselves are true to the 50s.” On a pragmatic note, he adds, “The sets are already built; although we’re going to enhance them a little bit, we’re basically happy with the product. That means we can spend more money on advertising than we did the last time we tried producing our own shows [at Water Tower Place].” Increased marketing could be a major factor in bolstering the theater’s name recognition and defining its identity.

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.

DeSantis is covering his bets, though: in January, Drury Lane Water Tower Place will host the national tour of the Broadway hit Xanadu. “I’m certainly not taking away the idea of using the theater as a rental house for the right product,” he says. “I need to find ways the theater can be viable in the community. We’re taking it one step at a time. If it works it opens a lot of doors for us. If it doesn’t, we’ll have to start looking for another way.”

aBuddy: The Buddy Holly Story runs 9/10-11/2, the Christmas-themed Meet Me in St. Louis 11/12-1/4/09. Upcoming Musical Monday performances this fall include Some Enchanted Cabaret: Rodgers & Hart & Hammerstein (9/22), Curtain Up! Broadway Showstoppers (10/27), and Cabaret Canteen: Music That Got Us Through (11/24). —Albert Williams