This took forever. And I'm still not sure it's 100% accurate. Inspired by @MatthewAlmont and many others.
  1. 1980: Star Wars: Empire Strikes Back
  2. 1981: Raiders of the Lost Ark
    This appears to be the only movie made in 1981 that I've seen.
  3. 1982: Annie
  4. 1983: Star Wars VI: Return of the Jedi
  5. 1984: This is Spinal Tap
  6. 1985: The Goonies
    Honorable Mentions: Back to the Future, Breakfast Club
  7. 1986: Ferris Bueller's Day Off
    Honorable mention: Top Gun
  8. 1987: The Princess Bride
    Honorable Mentions: Mannequin, Good Morning, Vietnam; Three Men and a Baby
  9. 1988: A Very Brady Christmas
    Honorable Mentions: Big, Coming to America, Twins, Bull Durham
  10. 1989: Steel Magnolias
    Honorable mentions: Little Mermaid, Field of Dreams, Dead Poets Society, When Harry Met Sally
  11. 1990: Pretty Woman
  12. 1991: Hook
    Honorable Mentions: Robin Hood Prince of Thieves, Point Break, Fried Green Tomatoes, Beauty and the Beast
  13. 1992: Aladdin
    Honorable Mentions: The Bodyguard, Mighty Ducks, A League of Their Own
  14. 1993: Mrs. Doubtfire
    Honorable Mention: Groundhog Day
  15. 1994: The Lion King
  16. 1995: While You Were Sleeping
    Honorable Mentions: Bad Boys, Tommy Boy, Clueless
  17. 1996: That Thing You Do!
    Honorable Mentions: Happy Gilmore, Independence Day
  18. 1997: Good Will Hunting
    Honorable Mentions: Titanic, Romy and Michelle's High School Reunion
  19. 1998: Playing By Heart
    Honorable Mention: A Bug's Life, Armageddon, Hope Floats
  20. 1999: Notting Hill
    Honorable Mentions: 10 Things I Hate About You, Office Space
  21. 2000: Miss Congeniality
  22. 2001: Bridget Jones' Diary
    Honorable Mentions: Harry Potter and The Sorcerer's Stone, Legally Blonde, Zoolander
  23. 2002: My Big Fat Greek Wedding
  24. 2003: Love Actually
  25. 2004: Harry Potter and the Prisoner of Azkaban
  26. 2005:Madagascar
    Honorable Mention: In Her Shoes
  27. 2006: Little Miss Sunshine
  28. 2007: Waitress
    Honorable Mentions: Harry Potter and the Order of the Phoenix, Dan in Real Life
  29. 2008: Baby Mama
    Honorable Mention: Mamma Mia!
  30. 2009:(500) Days of Summer
    Honorable Mention: Up in the Air
  31. 2010: Harry Potter and the Deathly Hallows Part One
    Honorable Mention: The King's Speech, True Grit
  32. 2011: Bridesmaids
    Honorable Mention: Harry Potter and the Deathly Hallows Part Two
  33. 2012: Pitch Perfect
  34. 2013: About Time
    Honorable Mention: The Way, Way Back
  35. 2014: Veronica Mars
  36. 2015:Star Wars VII: The Force Awakens
    Honorable Mentions: The Martian, Brooklyn
  37. 2016: Zootopia
    Currently the only movie I've seen in the theatre in 2016.