These are my top 3, but have watched them so much that they are now tinged with sadness. Just looking to coat other happy movies with a film of depression.
  1. The Birdcage
  2. Bridget Jones' Diary
  3. Manhattan Murder Mysteries
  4. When Harry Met Sally
  5. Always Tootsie
    Or Wayne's World 🌎
    Suggested by @angela3950
  6. Royal Tenenbaums
    (Honestly, it's been years since I watched this, but it's the first movie that came to mind)
    Suggested by @angusisley
  7. Clueless
    Suggested by @StuckOnThe7
  8. There Will Be Blood
    HEAR ME OUT! The film is so demanding that it requires all of your attention, thus fully distracting you from whatever is bringing you down
    Suggested by @Nicholas
  9. Whip It
    Suggested by @alanarogerrrrs
  10. The Goonies
    Suggested by @alanarogerrrrs
  11. Party Girl
    You can never go wrong with Parker Posey
    Suggested by @eatthelove
  12. The Full Monty
    Suggested by @dreadpiratemama
  13. Static
    Suggested by @dev
  14. Endless Summer
    When you got the winter blues, nothing beats a couple of surf bums chasing sun in the '60s. It's the quaint narration style that triggers the satisfying nostalgia endorphins.
    Suggested by @elooto
  15. Monty Python - Holy Grail
    Suggested by @aditim
  16. Breakfast Club
    Such a lovely distraction.
    Suggested by @Boogie
  17. Breakfast at Tiffany's
    Suggested by @rachelanne
  18. Heathers
    Suggested by @SarahMoore
  19. Jaws
    It never disappoints.
    Suggested by @kiraandlulu
  20. Step brothers
    Suggested by @tombatten
  21. Suggested by @sarahmccoy