(Photo by Warner Bros. Pictures/courtesy Everett Collection. The Iron Giant.)

The Best Movies of 1999, Ranked by Tomatometer

The Iron Giant and The Sixth Sense celebrate their 25th anniversaries!

Welcome to the best movies of 1999, ranked by Tomatometer!

1999 has a reputation for arguably the best year for movies of the ’90s, a strong feat considering its direct competitor is the dream team that was 1994’s cinematic batch. But for every Lion King, Pulp Fiction, Clerks, and Shawshank, 1999’s got an answer. Toy Story 2. Fight Club. Office Space. The Green Mile.

1999 was like a culmination of what had thrived during the decade, like the American independent cinema (literally the hilarious doc called American Movie), the adventure blockbuster (The Mummy), animation both computerized and traditional (Toy Story 2, The Iron Giant), increased international appetite (All About My Mother, Run Lola Run), and the entire Hollywood class of mid-budget adult thrillers, like The Thomas Crown Affair, The Talented Mr. Ripley, Arlington Road, Double Jeopardy…that list goes on.

One running theme of 1999 can be found concentrated in Being John Malkovich, American Beauty, Office Space, and Fight Club. An exploration of modern malaise and boredom, albeit from a specific middle-class vantage.

The introduction of the internet and screeching modems to homes across America fostered new, expanded, and sometimes clashing realities, put on screen with eXistenz, The Thirteenth Floor, and The Matrix.

Classic high school movies were also a 1999 forte, with American Pie, Election, 10 Things I Hate About You, SLC Punk, Never Been Kissed, Varsity Blues, Cruel Intentions, and But I’m a Cheerleader.

Comedies of all stripes thrived, from the romantic (Notting Hill), the controversial (Dogma, South Park: The Movie), black-lensed (The Wood, Life, The Best Man), and broad mainstream (Big Daddy, Austin Powers: The Spy Who Shagged Me, Analyze This).

The horror genre languished in the ’90s, but in its twilight we got the Sixth Sense/Blair Witch/Sleepy Hollow hat trick.

Continue on for our guide the best movies of 1999. It starts with every Certified Fresh film of the year. Those are followed by Fresh movies, and then Rotten movies with positive Audience Scores.