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FilmoFilia > Movie News > The 99 Best Films of 1999: Rolling Stone’s Rankings and Controversies
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The 99 Best Films of 1999: Rolling Stone’s Rankings and Controversies

Rolling Stone’s 99 Best Films of 1999 revisits a groundbreaking year in cinema. From "Magnolia" to unexpected omissions like "The Green Mile," the rankings ignite nostalgia and debate.

Allan Ford
August 18, 2025
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The Best Films of

1999 was a monumental year in cinema, often referred to as the last great year of the 20th century for movies. Rolling Stone magazine recently curated a list ranking the 99 best films of 1999, reigniting debates over which films truly defined the era. While classics like Magnolia and The Matrix dominate the top spots, the list also includes surprising omissions and controversial placements. Let's take a closer look at the highlights, the surprises, and what this ranking says about the enduring legacy of these films.

Contents
  • Rolling Stone’s Top Picks
  • Controversies and Omissions
  • A Closer Look at the Mid and Lower Rankings
  • The Legacy of 1999 in Film
  • Rolling Stone’s 99 Best Films of 1999

Rolling Stone's Top Picks

Topping the list is Paul Thomas Anderson's Magnolia, a sprawling, emotional drama that embodies the ambition of 1999's cinematic offerings. Following closely is the groundbreaking sci-fi masterpiece The Matrix, which redefined the action and sci-fi genres with its innovative storytelling and visual effects. Other notable entries in the top 10 include Being John Malkovich (#3), The Insider (#4), and Fight Club (#9).

Despite the critical acclaim for these films, Rolling Stone's choices have raised eyebrows, particularly for their inclusion of Wes Anderson's Rushmore (#10) and Sofia Coppola's The Virgin Suicides (#5), as neither strictly qualifies as a 1999 release.


Controversies and Omissions

Perhaps the most contentious ranking is Sam Mendes' American Beauty, placed at #87. Once celebrated as a cultural touchstone, winning five Oscars including Best Picture, its fall from grace reflects changing societal attitudes and the controversies surrounding lead actor Kevin Spacey. Rolling Stone's critique notes that the film's themes of suburban ennui and its iconic imagery have not aged well.

Adding to the debate, The Green Mile, a beloved audience favorite with a stellar IMDb score of 8.6/10, is entirely absent from the list. Fans of Frank Darabont's adaptation of Stephen King's novel may find it puzzling, especially when films like The World Is Not Enough (#93) and Big Daddy (#97) secured spots.

Spike Lee's Summer of Sam (#84) and Martin Scorsese's Bringing Out the Dead (#88) are also ranked surprisingly low, sparking discussions about the recognition of these lesser-known gems in the directors' filmographies.


A Closer Look at the Mid and Lower Rankings

The middle of the list features cult classics and animated favorites, including Office Space (#21), Toy Story 2 (#22), and The Iron Giant (#24). These films, though not at the forefront of critical acclaim during their release, have gained significant fan followings over the years.

In the lower rankings, Austin Powers: The Spy Who Shagged Me (#92) and Varsity Blues (#96) reflect Rolling Stone's eclectic approach, balancing high art with cultural phenomena that defined the late '90s.


The Legacy of 1999 in Film

Rolling Stone's rankings serve as a reminder of the extraordinary diversity of films in 1999, from introspective dramas to genre-defining blockbusters. This was a year when directors like Stanley Kubrick (Eyes Wide Shut), David Fincher (Fight Club), and Spike Jonze (Being John Malkovich) pushed the boundaries of storytelling.

While not everyone will agree with Rolling Stone's choices, the list highlights how cinema from this year continues to influence filmmakers and audiences alike.


Rolling Stone's 99 Best Films of 1999

  1. Magnolia
  2. The Matrix
  3. Being John Malkovich
  4. The Insider
  5. The Virgin Suicides
  6. Beau Travail
  7. Election
  8. The Straight Story
  9. Fight Club
  10. Rushmore
  11. The Limey
  12. The Sixth Sense
  13. Three Kings
  14. American Movie
  15. Eyes Wide Shut
  16. Topsy-Turvy
  17. South Park: Bigger, Longer & Uncut
  18. The Blair Witch Project
  19. Last Night
  20. Boys Don't Cry
  21. Office Space
  22. Toy Story 2
  23. Run Lola Run
  24. The Iron Giant
  25. The Talented Mr. Ripley
  26. Audition
  27. Lock, Stock and Two Smoking Barrels
  28. Notting Hill
  29. The Wind Will Carry Us
  30. All About My Mother
  31. Galaxy Quest
  32. Ghost Dog: The Way of the Samurai
  33. Mr. Death
  34. The Best Man
  35. Go
  36. 10 Things I Hate About You
  37. Star Wars: Episode I – The Phantom Menace
  38. Buena Vista Social Club
  39. Ratcatcher
  40. American Pie
  41. eXistenZ
  42. The Mummy
  43. Any Given Sunday
  44. Girl, Interrupted
  45. Cruel Intentions
  46. The Wood
  47. But I'm a Cheerleader
  48. Rosetta
  49. Cookie's Fortune
  50. The Hurricane
  51. Ravenous
  52. Holy Smoke
  53. Felicia's Journey
  54. Instrument
  55. Dick
  56. The Thomas Crown Affair
  57. Bowfinger
  58. Princess Mononoke
  59. Analyze This
  60. Jesus' Son
  61. Pola X
  62. Ride With the Devil
  63. The End of the Affair
  64. Judy Berlin
  65. October Sky
  66. Sleepy Hollow
  67. Deep Blue Sea
  68. Cradle Will Rock
  69. Stuart Little
  70. Limbo
  71. An Ideal Husband
  72. Sweet and Lowdown
  73. Miss Julie
  74. Titus
  75. For the Love of the Game
  76. Man on the Moon
  77. She's All That
  78. Tarzan
  79. Double Jeopardy
  80. The Muse
  81. Following
  82. The Cider House Rules
  83. The Winslow Boy
  84. Summer of Sam
  85. Flawless
  86. Mystery Men
  87. American Beauty
  88. Bringing Out the Dead
  89. Jawbreaker
  90. The Red Violin
  91. Black & White
  92. Austin Powers: The Spy Who Shagged Me
  93. The World Is Not Enough
  94. Angela's Ashes
  95. Music of the Heart
  96. Big Daddy
  97. Varsity Blues
  98. Boondock Saints
  99. Dogma

Personal Impressions

Rolling Stone's list is both a nostalgic trip and a catalyst for debate. While it's hard to argue against the brilliance of Magnolia or The Matrix, omissions like The Green Mile feel glaring. Personally, I find the low ranking of American Beauty a bit extreme, as the film's craftsmanship remains undeniable despite its controversies. However, seeing gems like Galaxy Quest (#31) and Notting Hill (#28) recognized reminds us of the incredible variety that 1999 had to offer.

What are your thoughts on Rolling Stone's rankings? Do you agree with their top picks, or were your favorites left out? Let us know which 1999 films you believe deserve more recognition!

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