The plot of the show is adapted from The Countess of Pembroke's Arcadia written by Sir Philip Sidney in the 16th century.

Head Over Heels opened at the Oregon Shakespeare Festival in June 2015, running for five months in their outdoor theater.

Head Over Heels is a jukebox musical that adapts the plot of The Countess of Pembroke's Arcadia, the 16th-century prose romance by Sir Philip Sidney.

Basilius and his loyal viceroy Dametas depart for the forest, with Gynecia reminding her hot-headed husband to listen to what Pythio has to say.

Basilius, for whom the new king is the most pressing matter, decides to leave Arcadia to find and slay him on the road, bringing everyone along so he can keep watchful eyes on his wife and daughters.

He lies to his family, explaining that Pythio only prophesied happy ends and that they must hunt a golden stag on the road.

On the road, Philoclea asks her sister and Mopsa, Dametas' daughter and Pamela's loyal handmaid, for advice about Musidorus.

Musidorus realizes that his journey was not well-planned, and worries that he may die in the forest before coming across a dead theatre troupe and their belongings.

Musidorus is able to evade Dametas' watchful eye with his female disguise, and is about to confess to Philoclea before a jealous and distraught Pamela interrupts them, destroying the room ("How Much More").

Philoclea is shocked that Pamela would be jealous of her and her new friend, and when Cleophila admits that she had reason to be, she realizes that the Amazon is actually Musidorus, and they embrace.

As the trip continues, both couples are happy in their new relationships, though Musidorus must also deal with the king and queen's feelings for Cleophila ("Head Over Heels").

Mopsa and Pamela are unsure of what their relationship means, but they are elated to find another couple like themselves when they witness Philoclea and Cleophila kissing ("Turn to You").

As she takes it, the fourth flag falls and, with all prophecies fulfilled, the citizens of Arcadia are struck with the loss of the Beat.

Realizing that they have traveled in a circle, the group considers how they have changed on their journey and vow to become a wiser and more accepting society with their new Beat ("Finale").

Also joining the re-imagined creative team were music supervisor Tom Kitt (who previously worked with Mayer on American Idiot) and Magruder to adapt Whitty's original libretto.

[16][17] The album features three bonus tracks: Turn to You (Pre-Prise), an acoustic version of "Automatic Rainy Day," and the Go-Go's performance of "This Town."

The album was engineered by Isaiah Abolin and Lawrence Manchester, produced by Scott M. Riesett and Tom Kitt, and co-produced by Louise Gund and Christine Russell.

[3] In Entertainment Weekly, Kelly Connolly viewed the show more favorably, praising "the charismatic cast" and Michael Mayer's "joyful production"; she gave the A− score overall.

[20] In March 2023, original librettist Jeff Whitty published an essay alleging severe mistreatment by the Broadway producers, his agent, and his lawyer, including—variously—exploitation, harassment, threats, and theft of royalties for Head Over Heels.