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Ranking the films of 1999, pt. 1

| Wednesday, October 2, 2019

JOSEPH HAN | The Observer

Brian Raftery’s 2019 book “Best.Movie.Year.Ever: How 1999 Blew Up The Big Screen” adopts an increasingly popular opinion among cinephiles: the last year of the 20th century witnessed more great films than any before it. 1999 was a watershed year for films of all stripes — from foreign-language pictures to special-effects blockbusters and everything in between. Over the next two days, I will rank the top-20 movies released in 1999.


  1. “The Iron Giant” (directed by Brad Bird)

Even if its retro fetishism and thematic morass now plays as a warmup to his later (and superior) “The Incredibles,” Brad Bird’s debut feature has plenty of character all its own. Twenty years on, Vin Diesel’s monosyllabic turn as the title character remains charming.

  1. “Eyes Wide Shut” (directed by Stanley Kubrick)

The famed director’s final film finds him returning to usual obsessions — emotional distance and male egocentrism — with ultimately diminished returns. Former real-life beaus Tom Cruise and Nicole Kidman’s performances as an estranged couple dominated tabloid headlines at the time, and are retrospectively the most interesting element of “Eyes Wide Shut.”

  1. “American Pie” (directed by Paul Weitz and Chris Weitz)

No, this update of bawdy ’80s comedies like “Porky’s” hasn’t aged particularly well. Very few comedies do, however; Conversely, very few movies period have a single scene as deservedly iconic as the one involving Jason Biggs’s hopeless romantic and the eponymous dessert.

  1. “Fight Club” (directed by David Fincher)

Fincher is one of the great feast-or-famine directors in history, and his most famous film lands squarely in the middle of those poles. Brad Pitt’s Tyler Durden has been adopted by the worst kind of dorm-room philosophers, but his bonkers performance is still one of his career peaks. For better or worse, this remains a film that everyone should see — if only so they can have an opinion on it.

  1. “Ten Things I Hate About You” (directed by Gil Junger)

This update of Shakespeare’s “Taming of the Shrew” doesn’t reinvent anything about the teen-movie genre, but it doesn’t have to. It has Heath Ledger, a marching band and “Can’t Take My Eyes Off You” — and if that’s enough for Julia Stiles’s Kat, that’s enough for the rest of us.

  1. “Boys Don’t Cry” (directed by Kimberly Pierce)

Hilary Swank won her first Oscar as the real-life Brandon Teena, a transgender man struggling to make a life for himself in rural Nebraska, and her bracing portrayal has only grown in stature since the film’s release.

  1. “Lock, Stock, and Two Smoking Barrels” (directed Guy Ritchie)

Ritchie’s exceptionally sleazy first feature is probably my favorite film of 1999, with Jason Statham’s acting debut and a knotty script combining to form a vibe that is best described as “Goodfellas” by way of Buster Keaton.

  1. “Toy Story 2” (directed by John Lasseter)

If there’s one thing Pixar is known for, it’s making films that can entertain and tug on heartstrings (and tear ducts) in equal measure. True to form, the “When She Loved Me” sequence in this film is perhaps the most emotionally affecting thing the studio has ever created.

  1. “Magnolia” (directed by Paul Thomas Anderson)

Please, if you can, forget the negative discourse around the frog-based ending to this film, and focus instead on the positive aspects of “Magnolia”: most importantly, a career-best performance from Tom Cruise. Even if the movie ultimately misses the mark, there’s something to be said for striking out with a big swing.

  1. “The Matrix” (directed by Lana Wachowski and Lilly Wachowski)

Come for the still-breathtaking special effects; stay for a muscular turn from Keanu Reeves that, beneath all the “whoa” memes, is stoic and athletic enough to recall both Clint Eastwood and Bruce Lee.


Check back tomorrow for the top-10 movies of 1999.

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