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Head Over Heels is a Jukebox Musical loosely based on Sir Philip Sidney's Arcadia combined with with the music of The Go-Go's. It tells the story of the royal family of Arcadia, King Basilius, Queen Gynecia, and their daughters Pamela and Philoclea. Problems are arising due to the daughter's love lives; Pamela refuses to marry any of her suitors, and Philoclea only has eyes on her childhood friend Musidorus, a penniless shepherd. Prophecies from the mysterious oracle Pythio lead Basilius to take his family on a journey away from their home, but as Pamela's handmaid Mopsa says, "a man can find his destiny on the way he takes to avoid it."

The show flopped on Broadway due to the odd pairing of Elizabethan language and 80s pop music, but the Cast Full of Gay caused it to develop a cult fanbase. The original cast featured Jeremy Kushnier as Basilius, Rachel York as Gynecia, Bonnie Milligan as Pamela, Alexandra Socha as Philoclea, Andrew Durand as Musidorus, Taylor Iman Jones as Mopsa, Tom Alan Robbins as Dametas, and Peppermint as Pythio.

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This musical contains examples of:

  • Abdicate the Throne: Pythio predicts Basilius will do this. He doubts it. He does eventually give the crown to his wife.
  • Adaptational Sexuality: Pamela and Mopsa were not in a romantic relationship in the orginal story.
  • Bed Trick: One of the few plot points kept around from the original story. The king and queen both make plans to meet up with Cleophila in a dark cave, but she gives their letters to each other without reading them.
  • Beta Couple: Mopsa and Pamela, though they rival the alpha couple in Act One.
  • Big Beautiful Woman: Pamela
  • Childhood Friend Romance: Philoclea and Musidorus as well as Mopsa and Pamela.
  • Disguised in Drag: Musidorus, as the Amazonian warrior Cleophila. He even decides to keep his female persona around!
  • The Glorious War of Sisterly Rivalry: Pamela (the Beautiful) and Philoclea (the Smart).
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  • "I Am" Song: "Beautiful" for Pamela, "Vision of Nowness" for Pythio, "Good Girl" for Philoclea.
  • Intercourse with You: "Heaven is a Place on Earth" turns into this.
  • Line-of-Sight Name: Three guesses who Cleophila first introduces herself to!
  • Lipstick Lesbian: Pamela
  • Magical Queer: Pythio, at first. They're eventually revealed to have been a citizen of Arcadia, banished after coming out.
  • Missing Mom: Mopsa has one. They come back.
  • Only Sane Man: Mopsa, to an extent.
  • Prophecy Twist: Played with. Most of the prophecies aren't too hard to decipher, but Basilius' stubborn nature makes him unwilling to think through them.
  • Quarreling Song: "Automatic Rainy Day"
  • Sexless Marriage: Basilius and Gynecia.
  • Sweet on Polly Oliver: The entire royal family except for Philoclea, ironically.
  • Transgender: Pythio identifies as nonbinary and uses they/them prounouns. Musidorus comes out as genderfluid near the end as well.
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