Skylight operates an arts-in-education program, called Enlighten, that provides free classroom workshops, residencies and performances for the Milwaukee Public Schools.
Sprague Vonier, the program manager at WTMJ television, public relations agent Clair Richardson decided to add to the cultural variety of Milwaukee by founding a coffeehouse, like those in San Francisco, with live beat poetry and folk music.
Soon, at a nearby fundraising event for another of their cultural projects, Bel Canto Chorus, two church musicians, Jim Keeley and Ray Smith, gave an impromptu performance of Gilbert and Sullivan songs.
A nearby outdoor space was acquired, and the company produced more small-scale Italian operas and operettas, alternating with Gilbert and Sullivan pieces.
The success of that project led to the company receiving a large grant to finance a two-year residency at the Skylight for Wargo.
The 2006–07 season included Humperdinck's Hansel and Gretel, South Pacific, the contemporary American comic opera Tartuffe, Smokey Joe's Cafe, and Gilbert and Sullivan's Patience.
The 2009–10 season included The Barber of Seville, Plaid Tidings, The Marriage of Figaro, A Day in Hollywood/A Night in the Ukraine and the first licensed production of Rent.
Pinafore, Jacques Brel Is Alive and Well and Living in Paris, Così fan tutte, a 2007 work by Joshua Schmidt and Adding Machine – The Musical.
Pinafore praised the performances, technical aspects and conducting and commented that the production "handsomely adds luster to the G&S tradition at Skylight.
[7] In June 2009, at the conclusion of the 2008–09 season, popular long-time artistic director Bill Theisen and several other staff members were dismissed due to a projected budget deficit and the economic downturn.
[12][13] On July 17, 2009, the Board sent letters withdrawing the contracts of two local actors over what the company considered disloyal comments on Facebook.
[14] This move, in turn, further angered Theisen, who revoked an earlier offer to direct four works on a freelance basis during the season.
[15] Former artistic director Richard Carsey, who had been asked to return to music direct two productions, next resigned, writing to the Board, "The Skylight is being destroyed by Eric and Suzanne's leadership.
[16] Over the next few days, two dozen of the other artists scheduled to perform in or work on the company's upcoming season resigned in protest at the firings.
Cabot soon announced that many of the artists who withdrew would return for the Skylight's 50th season, and Theisen agreed to direct the four productions that he had earlier offered to helm.