Favorite Films of 1999

In case you haven’t heard, 1999 was a great year for movies. I don’t remember seeing any of them in the theater at the time (I was 12), but I fondly remember watching and rewatching many on VHS and DVD later on.

I really tried to rank them. But the exercise of ranking felt even more futile and arbitrary than usual when I considered all the candidates and how I loved them nearly equally for different reasons. And so:

Top 10 films of 1999 I love nearly equally for different reasons, in alphabetical order

Dick

This gets funnier the more you know about Watergate. Choice scene: Haldeman’s house

Fight Club

Filmmaking as muscular as Brad Pitt’s abs. Choice scene: “The first rule of Fight Club.”

The Matrix

As a tween I babysat for a family that owned only a few DVDs, the only interesting one being The Matrix. Since the kids were always in bed by the time I arrived, basically I was paid to watch The Matrix. Choice scene: “I’ve been looking for you, Neo.”

October Sky

Jake Gyllenhaal has been great for a long time. Ditto Chris Cooper, who had quite the one-two punch with this and American Beauty. Choice scene: “He isn’t my hero.”

Office Space

In the Mount Rushmore of quotable comedies. Choice scene: “Sounds like somebody’s got a case of the Mondays!”

The Sixth Sense

Ah, the halcyon days of M. Night Shyamalan fever. Choice scene: “She wanted me to tell you she saw you dance.”

The Straight Story

What could have been a sentimental schlockfest is actually a graceful meditation on redemption and the cosmic importance of the quotidian. Choice scene: “That’s a darn good grabber, Alvin.”

The Talented Mr. Ripley

Could be titled Call Me By Your Name, which would work on several levels. Might be Matt Damon’s best performance. Choice scene: “Is there something you’d like to say, Freddie?”

Three Kings

This really owns the intersection of the “buddy comedy heist war movie” Venn diagram. Choice scene: “The blinding power of American sunshine”

Toy Story 2

In the Mount Rushmore of best movie sequels. Choice scene: Tour Guide Barbie

Bonus lists

Top 10 films of 1999 that aren’t “great” but are nostalgic favorites due to innumerable rewatches, in alphabetical order

• Austin Powers: The Spy Who Shagged Me
• Blue Streak
• Dogma
• Mickey Blue Eyes
• The Mummy
• Never Been Kissed
• She’s All That
• South Park: Bigger, Longer & Uncut
• Tarzan
• 10 Things I Hate About You

Top 6 highly regarded films of 1999 I don’t have strong feelings about, in alphabetical order

• American Beauty
• Election
• The Green Mile
• The Insider
• Magnolia
• Man on the Moon