Songfacts®:

• "Orlando In Love," the lead single from Japanese Breakfast's fourth album, For Melancholy Brunettes (and Sad Women), finds their leader, Michelle Zauner, venturing into literary territory. The song is a string-laden pop ballad inspired by the epic poem "Orlando Innamorato," by Italian Renaissance writer Matteo Maria Boiardo. It is described as Japanese Breakfast's take on American writer John Cheever's riff on "Orlando Innamorato."
  
  The album is the first from Japanese Breakfast since Jubilee in 2021. That album earned them airplay and TV appearances thanks to the popular track "Be Sweet."
• "Orlando Innamorato" (or Orlando in Love) is a sprawling poem published in bits and pieces between 1483 and 1495. It chronicles the misadventures of Orlando (the Italians' answer to France's Roland), a knight whose unrequited love for Angelica, a pagan princess, drives him to questionable decisions amid a backdrop of warring Christian paladins and Saracen invaders. Toss in a star-crossed romance between Bradamante and Ruggiero - she's a knight, he's a Saracen - and you've got enough melodrama to fuel an entire album cycle.
• The poem, famously unfinished, clocks in at a hefty 68.5 cantos, which provides the foundation for Michelle Zauner's cheeky opening verse:
  
  Orlando in love
  Writes 69 cantos
  For melancholy brunettes and sad women.
  
  It's a winking nod to the absurdity of poetic excess and a sly hint at the album's overarching theme: the rich and brooding terrain of melancholy, long regarded as the fertile ground where poets stand on the brink of inspiration.
• The press release paints the protagonist of "Orlando In Love" as a well-meaning poet who parks his Winnebago by the sea and, naturally, succumbs to the call of a siren. It's a vivid, slightly surreal image - part Midsummer Night's Dream, part seaside noir. The second verse sketches this scene with dreamlike precision, while the final verse leaves us pondering the perils of longing.
• Blake Mills provided the lush, string-adorned production. His resumé includes tracks by Alabama Shakes, Fiona Apple, John Legend and Feist.