Weathervane Playhouse, a Knight Arts grantee, knows how to put together a gala. This year, three-time Tony Award nominee (and Tony Award winner) Michael Rupert will be the headliner for the fest (and fundraiser to support the theater’s many productions and activities). He will perform as part of the ceremonies at the Weathervane gala, I♥WP, on Saturday, September 28.

Rupert, as Weathervane Playhouse noted, has blazed out an extraordinary 40-year career. He is an actor, singer, director and composer. On Broadway, he performed leading roles in such shows as “Pippin,” a revival of “Sweet Charity” (his Tony-winning role), “City of Angels,” “Falsettos” (for a Tony nomination), and “The Happy Time” (for another Tony nomination). That kind of work put him into contact with such theater legends as Bob Fosse, Julie Andrews and Stephen Sondheim. Not bad company.

As composer and writer, he won a Drama Desk Award for outstanding book for the off-Broadway play, “Guys Naked from the Waist Down.”

For Weathervane, Rupert will perform one of the highlight numbers from his latest Broadway show, “Legally Blonde,” on the Weathervane stage the night of the gala, which is being held in honor of our honorary chair, Thomas R. Trotter.

Michael Rupert. Photo courtesy of Weathervane Playhouse

Trotter once served as president of the Weathervane Board of Trustees. In that position, he oversaw the capital campaign in 1998 – which created three classrooms, a costume shop, scene shop, fly gallery and elevator – in an expansion project for Weathervane. It was much needed at the time. These areas were completed and dedicated in 2001.

A solo performance isn’t the only thing on Weathervane’s agenda. There will be food, prizes and a live and silent auctions featuring fine jewelry, tickets to Cleveland’s Playhouse Square for some 2014 season productions, vacation getaways, hot-air balloon rides and tickets to many local Akron area attractions.

Weathervane’s gala fundraiser, I♥WP, will begin festivities at 6 p.m. on Saturday, September 18, at Weathervane Playhouse, 1301 Weathervane Lane, Akron; 330-836-2626; www.weathervaneplayhouse.com. Tickets are $175 (Amorous Patrons) and $125 (Loving Admirers).