In an annual series, Every Movie Has a Lesson is going to look back twenty years to revisit, relearn, and reexamine a year of cinema history to share favorites, lists, and experiences from the films of that year.

1999! Man, what a time it was to be alive. That Prince song finally came true, Y2K be damned. I was a 20-year-old college junior and loving life. Can we go back yet?

Looking back, many cinephiles and experts put 1999 right next to 1939, 1969, and 1982 are one of cinema’s greatest years. Seeing the year’s impact 20 years later, I cannot argue with that distinction from an historical impact between the many emergent movies of future auteurs, the peak of the now virtually extinct mid-budget programmers, and the increasing reach of cell phones and the internet. Personally, I like the movies from last year, 1998 (and even 1997 too), better than 1999, but history wins and I’ll grant 1999’s earned place.

Just as I did last year, I need to offer a personal level of clarification when I build and justify lists like the one you’re going to read below for 1999. That challenge is that there can often be a distinct difference between a movie that is considered one of the “best,” respected and revered on technical and artistic levels, and something held dear as a personal and subjective “favorite.” I find myself torn between “bests” and “favorites” all the time, every year present or past, when creating any “10 Best” list as a credentialed film critic. Call it an occupational hazard. Alright, as Prince said, let’s party like it’s 1999.

(All poster images from IMDb)

The 10 Best Movies of 1999

I’ll have dig through my old college archives, but there is a good chance 1999 was the first year I ever printed a “10 Best” as a wannabe film critic writing for The Observer student newspaper at Saint Joseph’s College in Rensselaer, Indiana. I would have been a well-traveled junior who was consuming more movies with each year. If memory serves me write 20 years later at the age of 40, I’m pretty sure my #1 then was The Green Mile, meaning my top spot has changed with time and I’m not surprised by what. The Matrix is an undeniable game-changer for its era and the kind of movie that is a dual “favorite” and “best” on my lists when I vote with my head or my heart.

One of the films that really moved me in 1999 and does so still today is The End of the Affair. I know I was swept by the torrid World War II romance, Graham Greene’s prose, a fetching Julianne Moore, and the powerful drama in the mold of The English Patient. Easily the most under-seen of my Top 10 is Arlington Road at #4. It’s probably one of my most recommended “blind spots” I share with others who want, as they always say, “something different.” It’s a frighteningly topical pre-9/11 terrorist film that makes you shudder harder today.

Beyond that, I was a big fan of Norman Jewison’s The Hurricane and have long been a Denzel Washington worshipper. However, I cannot deny the power and historical impact that American Beauty and Fight Club have generated in two decades. They are watersheds, even if I didn’t see their full greatness as a younger man. The end of my list is closed by two perfect dark comedies (which is subjectively hard to say) and cult classics in Office Space and Election. Election was the real head-turner, dropping its acidic wit in a peak year of the high school movie genre. Finally, no top list of 1999 is complete without The Iron Giant. It beats the best of 1999 by Pixar or Disney by a country mile.

The Next 10 Best:

11. The Thomas Crown Affair

12. For Love of the Game

13. Notting Hill

14. Toy Story 2

15. Ghost Dog: The Way of the Samurai

16. Bringing Out the Dead

17. Tarzan

18. The Cider House Rules

19. Three Kings

20. Magnolia

Once again, going back to that young college kid’s brain, I can guarantee you I had The Thomas Crown Affair and For Love of the Game in my Top 5 back then. I think the Pierce Brosnan vehicle is a ultra-cool heist film remake that easily improves on the original, even against Steve McQueen. It’s probably the 1999 movie I’ve re-watched the most in 20 years. It’s instantly entertaining. I know Bull Durham and Field of Dreams will always be bigger baseball films for Kevin Costner, but I have a romantic sweet spot for Sam Raimi’s little gem where the a guy reflecting on how he blew it with his girl takes precedent over the sport for two hours.

I’ll go with a deep cut in giving a spot to Jim Jarmusch’s Ghost Dog: The Way of the Samurai. I’m not really a Jarmusch guy, but damn, Forrest Whitaker was outstanding and the zen tension dichotomy of that movie builds well. I’ve always felt that Bringing Out the Dead was ballsy and underrated Scorsese. It absolutely still zips now. The same goes with Three Kings, which feels ahead of its time. Tarzan makes the list because, at the time, Disney finally made an animated movie with a non-princess lead for a dude like me.

Lastly, go ahead and call me out, film snobs, for having Magnolia this low. It was lucky to make the list. It needs a re-watch from me because it confounded and maddened me back in 1999. It’s aged well, but that one is still going to take time. Call me again in 2039. May by then I’ll be playing Vulcan Vegas no deposit bonus. As always, it loses me at the frogs.