Jeff Whitty Go-Go’s for broke with ‘Head Over Heels’

“This is my new world of outdoor theater,” Jeff Whitty says of the rain pouring down on a gray Ashland afternoon. “The rain and the owls.”

The Tony-winning playwright of Avenue Q is hard at work on his new play, Head Over Heels, which will open at the Oregon Shakespeare Festival’s outdoor Elizabethan Theatre on June 3, and the weather is not cooperating. He shrugs it off.

“I’ve always felt theater should be like sports,” he says. “This is the closest I’ve had to if it’s raining at the football game, then people just soldier on. People have their parkas. But I say as the one that gets to stay under the overhang.”

Luckily all the costumes are rain-proof. As for the owls, he advised the cast to stop the show and do their best to translate.

The Elizabethan Theater is the same stage where Whitty, a Coos Bay native, saw his first-ever professional theater production, and the same where his play The Further Adventures of Hedda Gabler played in 2008.

Unlike Gabler’s run at OSF, Head Over Heels is a world-premiere. And an incredibly unlikely one at that.

For one, it’s a musical, which OSF hasn’t historically specialized in, and Whitty, wasn’t interested in after the relative tanking of his adaptation of the 2000 cheerleading film, Bring it On.

“It ran five months on Broadway,” he says. “But didn’t hit the right way. It just wasn’t in the pocket. It sent me into a huge depression.”

He moved to LA and swore off musicals, even though his agent kept trying to pitch him on a jukebox project using the music of ’80s icons, The Go-Go’s.

But then Whitty had a real left-field idea: “What if it’s not in the 1980s, but based on this thing I read at the University of Oregon called The Old Arcadia?” he says.

For the uninitiated, The Old Arcadia is an epic 16th-century prose piece about a king trying to outrun the ill effects of a prophecy handed down by the oracle at Delphi. It was written by poet Sir Philip Sydney, and then rewritten by either him or his sister, The Countess of Penbroke. His original text was lost until the early 1900s, earning it the label “The Old Arcadia,” when it was rediscovered.

“I had this thought: ‘what if I mash them together?’” says Whitty. “I like to do things that are in opposition. Like, for Avenue Q, it was how do you tell an adult story for puppets.”

Strangely enough, that jived well with The Go-Go’s, who Whitty says were fine with their music being used for a play, but didn’t want to see their story put on stage eight times behind the week.

“They already have the best VH1 Behind the Music story ever,” says Whitty.

Whitty got to work, adapting the story to be about an epic road trip to Bohemia and working the songs in along the way.

“I like re-contextualizing for the audience so it’s like, ‘here’s what’s familiar and then here’s how it’s totally new,’” he says. “A total reinvention.”

One place that reinvention is very evident is during the song “Vacation,” which despite sounding like a breakup tune, Whitty says is actually about trying to escape the grips of heroin, a sadness Whitty embraced by slowing down “Vacation’s” dancy tempo.

And now?

“It’s the most beautiful ballad without changing a word of it,” he says.”

Key to making that happen was the work of music director Geraldine Anello, whom Whitty insisted on bringing along for this show to give her “her big break.”

Another member of the crew Whitty brought with him to the show is costume designer Loren Shaw, whose costumes are so ambitious he feels they might actually be upstaging him.

“I’m so jealous,” he says. “Because I dress up for the rehearsals, and I’m like ‘damn you. I would just love to wear that at Burning Man!’”

But the costumes and choice of music aren’t the only elements of Head Over Heels that are going for broke. It’s also entirely in verse, a change Whitty introduced to trim his original script after discovering it was too long. He made the update in a four-day writing blitz.

“I was like a meth addict, except it was iambic pentameter instead of drugs,” he says.

And in many ways, that blitzkrieg serves as a metaphor for the show as a whole. It’s a musical comedy mashup jukebox reboot in period language from two eras half a millenia apart. In a word: ambitious.

“There will be no middle ground with this,” says Whitty. “It will be a massive hit or a spectacular failure. We’re not hedging our bets.”

Head Over Heels

June 3-October 10

Oregon Shakespeare Festival, 15 S. Pioneer St., Ashland

$30-$115