Skylight has one of the most colorful histories of any company in the nation. Its genesis came during a party in the late 1950s, when some friends lamented the paucity of culture in Milwaukee. They put together $2,000 and opened a coffeehouse. A surprise hit of Gilbert and Sullivan selections in the space’s second floor launched what soon became the present company. With seemingly boundless energy—one year saw a dozen productions—Skylight embarked on an eclectic mix of musical theater: musicals, Baroque and chamber operas, Gilbert & Sullivan and other operettas, and revues.

The company took a big jump forward in the mid-1980s when future superstar directors Stephen Wadsworth and Francesca Zambello took over the artistic reins at the beginning of their careers. And on the verge of its 50th anniversary in 2009, an internal eruption attracted the attention of the New York Times, which termed it “a case of ‘Figaro’ meets ‘Fargo’ (minus the wood chipper).”

With the dust settled, the company continued its hectic annual schedule of nearly 100 performances—almost always sung in English—and added an open-air summer program. Its primary five-work season in the intimate (358-seat) Cabot Theatre is complemented by the even smaller Studio Theatre and free post-performance cabarets. The company also has an active education program which partners with Milwaukee schools and includes touring, student writing and performing, and other activities.