Iconic Movies That Defined 1999: A Year in Film

With another month, it is time to do another year in movies. This year is 1999. 1999 was my first full year of existence as I was born in December of 1998 so while I still didn't see any of these when they came out, I was alive. This year had a lot of great movies from popular directors as well as launches or relaunches of popular Sci-fi franchises.

The highest grossing movies of 1999 were

1. The Phantom Menace ($924,000,000)

2. The Sixth Sense ($673,000,000)

3. Toy Story 2 ($487,000,000)

4. The Matrix ($464,000,000)

5. Tarzan ($448,000,000)

6. The Mummy ($418,000,000)

7. Notting Hill ($364,000,000)

8. The World Is Not Enough ($362,000,000)

9. American Beauty ($356,000,000)

10. Austin Powers: The Spy Who Shagged Me ($311,000,000)

There were a lot of memorable family and animated movies that came out this year with many being a continuation or remake of a popular TV show or kids book such as

• Doug's First Movie

• South Park: Bigger Longer and Uncut

• Pokemon: The First Movie

• Dudley Do-right

• Inspector Gadget

• Stuart Little

There also several standalone family films such as

• Baby Geniuses

• Muppets from Space

• The Iron Giant

• Fantasia

There were a few horror films from this year that were semi popular

• The Rage: Carrie 2

• The Blair Witch Project (majorly popular and launched the found footage subgenre)

There were also a lot of well known directors that released another film in their impressive filmographies such as

• Lock Stock and Two Smoking Barrels (Guy Richie)

• Eyes Wide Shut (Stanley Kubrick)

• Sleepy Hollow (Tim Burton)

• Bringing Out the Dead (Martin Scorsese)

• Fight Club (David Fincher)

• Magnolia (Paul Thomas Anderson)

• For Love of the Game (Sam Raimi)

• The Sixth Sense (M. Night Shamylan)

On the thriller front the year got films like

• Run Lola Run

• The Thomas Crown Affair

• True Crime

• Deep Blue Sea

• The Talented Mr. Ripley

• The Mod Squad

• 8mm

There were also a couple of standout romance films like

• She's All That

• Cruel Intentions

1999 also saw the release of several iconic comedies such as

• Wild Wild West (Fun Fact: Will Smith turned down the Matrix to star in this film)

• American Pie

• Being John Malkovich

• Galaxy Quest

• The Story of Us

Finally, on the drama front there were films like

• October Sky

• Tumbleweeds

• The Green Mile

• Bicentennial Man

• Any Given Sunday

For the Oscars, the five films that got nominated for best picture were

• American Beauty (Winner)

• The Cider House Rules

• The Green Mile

• The Insider

• The Sixth Sense

I saw 14 films from this year, with the majority of them being the most famous ones. Here is a quick ranking of the films I have seen from 1999.

14. Deep Blue Sea

Deep Blue Sea is just a dumb shark movie from this year. It isn't high quality but is still fun to watch. The movie is lots of nonsense but somehow landed both Samuel L Jackson and Stellan Skarsgard. But in the end if I am in the mood for some dumb fun, I will put on this movie.

Score: 5.5/10 Grade: C

13. Fantasia

Fantasia is just a bunch of shorts put to classical music. It's not really much in terms of a movie but if you like classical music this will be interesting for you. I don't really want to watch concert shorts. The only thing I liked about this film is that it features the famous Sorcerer Mickey short.

Score: 6.5/10 Grade: B-

12. Sleepy Hollow

Sleepy Hollow is Tim Burton's big release of this year. I like the mystery aspect of this film with Icabod Crane. The movie also has a pretty stacked cast with Dumbledore, Uncle Vernon, Christopher Walken, Alfred, and Emperor Palpatine. However, the movie gets kind of bogged down when it gets into the reveals of who is behind the killings.

Score: 6.5/10 Grade: B-

11. The World is Not Enough

This was a fairly decent James Bond movie. I liked how it goes into the past mistakes of M and her past, however, Skyfall does that better. Where the movie loses me is with the over the top nature of the villain. With his ability to not feel pain, he seems more like a villain from a Superhero movie than a spy movie. It is definitely one of the weaker Pierce Brosnan films.

Score: 6.5/10 Grade: B-

10. Star Wars: Episode 1 - The Phantom Menace

The Phantom Menace was such a big deal in 1999 but ultimately left many disappointed. There are some pretty solid moments in this between the final battle, the lightsaber stuff, and Darth Maul. I also didn't mind the Podracing scene. The movie just gets too bogged down with Senate hearings, Naboo politics, and Gungans, none of which you really want in a Star Wars movie.

Score: 6.5/10 Grade: B-

9. Magnolia

Magnolia is a film I appreciated more than I enjoyed. This movie features great performances from its entire cast. Tom Cruise plays such a different role than he normally does. I also thought it was interesting how all of these different stories are loosely tied together. However, this type of movie just isn't really my kind of thing. I can appreciate the craft but wish it was a little more streamlined in the plot. 

Score: 7.5/10 Grade: B

8. Eyes Wide Shut

Eyes Wide Shut is another film that I appreciated more than I enjoyed. I thought the film had this interesting thrilling and mystery aspect to it as we follow Tom Cruise on edge from this organization he encountered. However, this story is just a little too erotic and sexually charged as the entire plot is driven by this man coping with his wife potentially having an affair. 

Score: 7.5/10 Grade: B

7. Tarzan

Tarzan is an iconic Disney movie. It has a great soundtrack from Phil Collins and a lot of fun characters. I thought this was one of the more effective love stories from Disney as we see Tarzan and Jane learn from each other and grow.

Score: 8/10 Grade: B

6. Galaxy Quest

Galaxy Quest is a fun parody of Sci-fi films and culture while also setting itself apart as its own thing. It digs the most at the Star Trek fanbase but is still a lot of fun to watch. It has as tacked quest with Tim Allen, Sigourney Weaver, Alan Rickman, Sam Rockwell and even a small early role with Dwight Shrute.

Score: 8/10 Grade: B

5. The Talented Mr. Ripley

This was a very effective thriller. It is all about a guy that goes too deep with his lies and has to somehow get him self out without consequences. Matt Damon is great in this role with the movie also featuring Gwyneth Paltrow, Jude Law, Cat Blanchett and Phillip Seymour Hoffman.

Score: 8/10 Grade: B

4. Toy Story 2

Toy Story 2 is one of my favorite Toy Story movies as it is the one that was popular when I was the perfect age. I like how the movie builds on Woody's backstory as well as making him cope with the idea of Andy getting older. I also like how it let's Buzz and the other toys take on more of a heroic roll.

Score: 8.5/10 Grade: A-

3. Fight Club

Score: 9/10 Grade: A

2. The Sixth Sense

I watched this movie for the first time in 2026 and thought it was a very good drama thriller. I went in knowing the big twist (it is hard to avoid spoilers for a very popular 27 year old movie) but I felt the movie was just a good knowing as it gives a new perspective on the characters. I thought Bruce Willis was great in the movie and played this child psychologist very well.

Score: 9.5/10 Grade: A

1. The Matrix

The Matrix is one of best and most iconic movies of all time. It takes everything great from Sci-Fi, action and martial arts movies and puts them all together. The world building here is masterfully done and the action is top notch. It is such a shame that the franchise went so downhill after this film.

Score: 10/10 Grade: A+