Raindrops Keep Falling on Cusack

Rain has always been more than weather in John Cusack’s world, it’s a mood. From heartbreak under a gray sky to shootouts in a storm, Cusack seems destined to share the screen with raindrops. So while the skies open up, here’s a soundtrack to match his most unforgettable downpours.

Romantic Rain

  • Say Anything… (1989) Cusack’s iconic Lloyd Dobler has a heartbreak-in-the-rain moment. The perfect starting place for teenage angst and puddle-soaked love.
  • The Sure Thing (1985) A road trip rom-com where Cusack gets caught in a cold downpour with Daphne Zuniga. Young Cusack + rain = awkward charm.

Quirky Melancholy

  • Better Off Dead (1985) Lane Meyer (Cusack) wallows in heartbreak, complete with a rain gag that turns melodrama into comedy.
  • High Fidelity (2000) Adult Cusack, older and still brooding, wandering in the rain to reflect on love, loss, and mixtapes.

Dark Drama

  • Midnight in the Garden of Good and Evil (1997) Gothic Savannah storms and Southern humidity match the mystery Cusack’s character gets drawn into.
  • Grosse Pointe Blank (1997) Martin Blank’s assassin life comes to a climax with shootouts and drenched streets, violence and rain go hand in hand.

Psychological Storms

  • Identity (2003) Practically the rain movie. Cusack and a group of strangers are stranded at a motel during a relentless thunderstorm, unraveling a surreal murder mystery.
  • 1408 (2007) Paranormal horror, with lightning and stormy rain outside the cursed hotel room. Cusack alone in the storm, both inside and out.

John Cusack Rain Playlist

Romantic Rain (80s Heart-On-Sleeve)

  • Peter Gabriel – “In Your Eyes” (Say Anything…)
  • The Cars – “Drive” (The Sure Thing)
  • Howard Jones – “Like to Get to Know You Well” (Better Off Dead)

Quirky Melancholy

  • Stevie Wonder – “I Just Called to Say I Love You” (jokingly from High Fidelity)
  • Elvis Costello – “Shipbuilding” (High Fidelity mood match)
  • The Jam – “Town Called Malice” (High Fidelity soundtrack gem)

Dark Drama

  • Tony Bennett – “I Left My Heart in San Francisco” (Midnight in the Garden of Good and Evil)
  • The Clash – “Rudie Can’t Fail” (Grosse Pointe Blank shootout scene)
  • Violent Femmes – “Blister in the Sun” (Grosse Pointe Blank)

Psychological Storms

  • The Carpenters – “We’ve Only Just Begun” (1408 creepy use of cheerful music)
  • Frank Sinatra – “It Had to Be You” (Identity eerie rain motel vibes)
  • Eurythmics – “Sweet Dreams (Are Made of This)” (1408 atmosphere match)

Closing the Marathon

  • Nick Drake – “Northern Sky” (fits the rainy reflective mood perfectly)
  • Echo & the Bunnymen – “The Killing Moon” (dark and poetic, the storm’s last word)