The Caldwell Theatre may be South Florida's oldest theater company still in operation, but there was a time when it didn't have the esteem of the county's dramatic powerhouses, Mosaic and Dramaworks. In the mid- to late '00s, the theater's forte seemed to be conventional, familiar audience pleasers rather than provocative think pieces — a pair of Steel Magnolias for every Doubt. This is no longer the case, particularly since Clive Cholerton took over the reins as artistic director. After a bumpy first season beset with actor injuries and less-than-stellar selections, Cholerton turned the Caldwell into a regular hit factory in 2011 and 2012. It offered hip and thoughtful shows like the fact-based hoarding dramedy Stuff, the American postwar panorama Six Years, the political domestic drama After the Revolution, the satiric pro-wrestling comedy The Elaborate Entrance of Chad Deity, and the of-the-moment and pro-labor musical Working. The fact that the Caldwell is heading toward bankruptcy protection from unpaid loans at the height of its artistic success is a tragic irony.