Part Go-Go’s tribute, part gender statement, joyous ‘Head Over Heels’ works as both

When trying to describe “Head Over Heels,” the fresh-from-Broadway musical currently bopping its way into audiences’ hearts at Theater Wit, it’s hard not to sound like a Mad Libs. Case in point: Adapted from Phillip Sydney’s 16th century pastoral prose romance “The Arcadia,” “Head Over Heels” features the music of ’80s New Wave icons the-Go-Go’s and a book written (in part) by “Avenue Q” scribe Jeff Whitty. See? And yet, this dramaturgical décolletage is somehow electrically eclectic. Go figure.

All those elements collide most delightfully in co-directors Derek Van Barham and Elizabeth Swanson’s shaggily vibrant rendition of the show for Kokandy Productions. A winning cast filled with knockout singers certainly helps, as does the Chicago storefront joie-de-vivre that permeates the entire production. While it occasionally seeps over into sloppiness, this production’s joyous, theater-kid oomph, with music direction from Kyra Leigh and choreography from Breon Arzell, pairs nicely with Jeff Whitty and adaptor James Magruder’s wooly sense of whimsy — not to mention the Go-Go’s tunes, which just plain rock.

The action begins in the ancient Greek kingdom of Arcadia, where the Go-Go’s hit “We Got the Beat” is repurposed into an exuberant exaltation of small-c conservatism: Arcadia’s grumpy king, Basilius (Frankie Leo Bennett), is just trying to do things the way that they’ve always been done. End of story.

OK, not so much: There is a major complication in his eldest daughter Pamela (Bridget Adams-King, a fast-rising star) and her refusal of every suitor he puts before her, possibly because she has the mutually reciprocated hots for her handmaiden, Mopsa (Deanalis Resto). Oh, and his youngest daughter Philoclea (Caitlyn Cerza) is also in love with a poor shepherd, Musidorus (a superb Jeremiah Alsop), but that idea is so absurd to Basilious that he barely bothers to brush the man off when he asks for her hand in marriage.

Unfortunately for Basilius, the new oracle at Delphi — a self-identified “nonbinary plural” figure with a mischievous streak named Pythio (played by the sublime Parker Guidry) — has other ideas. Pythio hands down four prophecies that spell doom for the king’s vision of his family, his future and his kingdom that send Basilius racing to undo them, dragging his wife, Gynecia (Liz Norton), his daughters, his chief advisor Dametas (Shane Roberie) and their entire retinue into the forest on the pretense of a golden stag hunt. (Pro tip: In pastoral comedies, forests are where everything goes screwy.) The family is pursued by Musidorus, who arrives — thanks to a tip from Pythio — disguised as an Amazonian warrioress. The whole family immediately falls in love and/or lust with “Cleophila,” (look, inventing fake names is hard) and sexy, gender-fluid shenanigans ensue.

Old-school audience members who are accustomed to the gender-bending in Shakespearian comedies like “Twelfth Night” will recognize the similar tropes at play in “Head Over Heels.” In fact, gender is one of the musical’s primary concerns. Simply put, it finds the subject quite open to interpretation, taking the gender-fluid themes subtly present in Shakespeare’s cross-dressing comedies and slapping them on the marquee.

Younger audiences, on the other hand, will likely understand these things less as literary signifiers than as, well, just the way things are nowadays. They’re much more likely to be confused by the classical language — or, for that matter, the music of the Go-Go’s. In that sense, “Head Over Heels” has something for everyone, as well as something to push them out of their comfort zone. Really, the whole show is one big mess of people, comfort zones, and the two being forcibly yanked apart — only for the characters to discover that this strange new gender-fluid world fits them quite fine.

“Head Over Heels” is an odd beast, but it’s also a thrillingly queer one. The emotional beat that strikes the hardest revolves around a simple swapping of pronouns in one oft-repeated refrain. And when the show pokes fun at itself via Musidorus stumbling across a deceased theater troupe, reportedly starved “for lack of a serious message,” it does itself a slight disservice. Its messages are quite serious, actually. It’s just that they’re being presented in an unserious manner. The show is simultaneously a goofy jukebox musical and an earnest treatise on evolving gender norms. It is both, and it’s not quite either. How fluid indeed.

Alex Huntsberger is a local freelance writer.