19 More for 1999

I love lists. Movie lists especially. So whenever I see someone create a list, it grabs my attention. When I saw the “Must See Movies from 1999” list from @Film School Rejects, I knew it was going to be something I’d enjoy reading. At that time in my life, one of my uncles had given me some movies to watch that really started my interest in exploring movies further. It also happened to be a year that produced quite a few movies that are worth watching, as I would come to find out as I read the list from Film School Rejects and looked to see what other films I might’ve included.

Their list is great. It includes some movies that I absolutely agree should be considered “Must See”. It also had a couple movies I hadn’t heard of before which I’ll certainly be looking forward to watching after reading their recommendations. But as I looked through the list of movies from 1999 which didn’t make their list, I found myself thinking that there were likely 19 more movies that could arguably make their list as well.

I’m not going to argue which movies could or should be removed from their list to make room for some of mine, and I’m also not going to try to rank order my movies in terms of how vehemently I’d argue for their addition. Just like with their list, I’ll order mine alphabetically, with some honorable mentions at the end because it was hard narrowing it down to just 19, even if that puts the overall combined list over 40 movies.

American Beauty

This Kevin Spacey movie was never one of my favorites, nor did I gush over it like a lot of movie lovers did, but it won Academy Awards for most of the top categories – Best Picture, Best Director, Best Original Screenplay, Best Actor, and Best Cinematography. While I often disagree with the results of the Oscars, there’s no denying that it’s at least one of the best movies of that year, if not the entire decade. Because of that, almost all movie buffs have seen it or at least have it on their list of movies to watch, but on the off chance that it isn’t on someone’s list, it should be.

Any Given Sunday

I remember going into the theater to watch the film, expecting an entertaining football movie with Al Pacino there to add some gravitas as the head coach. What I got was a gritty look into the world of professional sports, shining a light on things I hadn’t thought about before regarding the physical, mental and emotional toll the game has on athletes and coaches trying to build and sustain careers in a sport that doesn’t love them back. I was blown away, and I consider this to be a “Must See” film for anyone who loves professional football.

Being John Malkovich

I don’t know what compelled me to see Being John Malkovich, but even if I had any expectations for what it might be like, they were certainly obliterated. John Cusack is one of my favorite actors, with many, many memorable moments in his filmography, but this movie was such a “mind-scrambler” (that’s the PG way of saying it anyway) that I came away just trying to figure out what was going on. That said, for people who like experimental, philosophical, “different” movies that might be considered “avant garde”, Being John Malkovich is one that should be on the list of films to watch.


One of my favorites, Bowfinger is a really clever movie that I consider to be one of the best movies in the filmographies of both Steve Martin and Eddie Murphy. It’s also probably the last really good live-action movie Eddie Murphy made before a string of… regrettable movies in his filmography (“Dreamgirls” not withstanding). Additionally, I’ve found that many movie lovers have dreams of someday working to make a movie themselves, the movie-within-a-movie aspect of Bowfinger is also a lot of point of interest.


Kevin Smith built his considerably large and loyal fanbase in the 90s through Clerks, Mallrats, and Chasing Amy, but Dogma felt like he was taking things to another level. He went from movies that felt like they could be shot on a hand-held camera to having what feels more like a big budget blockbuster with some serious actors in its cast. The scope of the plot also goes from his previous films being more intimate, personal storylines, to a place where Dogma takes on religion and Good vs Evil in an irreverent way.

Drop Dead Gorgeous

Perhaps the least prominent film on this list, it’s a fantastic mockumentary featuring a cast including Denise Richards, Kirsten Dunst, Allison Janney, Ellen Barkin, Brittany Murphy, Kirstie Alley, and Amy Adams in her first film role. I distinctly remember going to see this movie and being surprised that no one else was talking about it even a year later. It’s definitely one that I would recommend on occasion while working at Blockbuster in one of the summers which followed.


Reality TV was already considerably popular back in 1999 and with EDtv, Director Ron Howard took a satirical look at people becoming famous through sharing their unfiltered lives on television, the voyeuristic fandom that often turns toxic, and the negative impacts it has on the lives of those involved. The Truman Show gets far more praise for sharing a similar message, but I’d argue that EDtv does it just as well in a more realistic way. The cast of EDtv is also excellent for a movie that doesn’t get talked about much, with Matthew McConaughey, Woody Harrelson, Jenna Elfman, Martin Landau, Dennis Hopper, Elizabeth Hurley, Ellen DeGeneres, Rob Reiner, and Sally Kirkland.


It’s hard to explain why I like Go, but to me, it just feels like a 90s movie at its core with its pacing, its tone, its coming-of-age story with lack-of-gloss-bordering-grittiness, and its style, all a credit to Director Doug Liman. The soundtrack was really good (I still have the CD somewhere), and its cast that included Timothy Olyphant, Katie Holmes, Jane Krakowski, William Fichtner, Breckin Meyer, Scott Wolf, Jay Mohr, Taye Diggs, and the film debut of Melissa McCarthy. The intertwining plot was also partially what made this such an interesting film that was fun to rewatch.

Happy, Texas

This is one of the two movies on the list that I’d guess many people hadn’t seen, although they might mistakenly think I’m referencing the movie Paris, Texas here. I can assure you, this movie is as far removed from that movie as the state of Texas allows. It’s a hilarious case of mistaken identity and served as my introduction to the great Steve Zahn, and has a great performance by William H. Macy in his role as the local sheriff trying to find his identity. It’s a movie that I’d watch just about any time if I saw it show up on a streaming service, although I’m more than happy to grab the DVD off the shelf for re-watches. I’m yet to introduce this to someone who ends up not enjoying it.

Man on the Moon

Having seen a bit of Andy Kaufman’s work and having heard of his reputation as a comedic genius, I was absolutely interested in seeing Jim Carrey, the top comedic actor of the 1990s, portray him in a biopic. While I was prepared to learn a lot about why Andy Kaufman was a genius, I don’t think I was fully prepared to see just how great Jim Carrey could be as an actor. I had probably seen The Truman Show at that point, which he’s very good in, but what he does in Man On The Moon was transformational. It almost certainly opened the door for him to get cast in more serious roles like The Majestic and Eternal Sunshine Of The Spotless Mind. For anyone who enjoys comedies (which is everyone, right?), this should be a “Must See” as it provides a good depiction of who Andy Kaufman was, and shows Jim Carrey’s incredible range.

Mystery Men

Unlike today, the cinematic landscape of 1999 wasn’t as full of superhero movies. There had been a few, and the Ben Stiller helmed comedy Mystery Men did a great job of respectfully spoofing the genre. These heroes aren’t capable of going head-to-head with the Avengers, Justice League, or even The Suicide Squad, but the cast does a wonderful job of mixing together heart and laughs. Given that there have been over 25 big superhero films since its release, Mystery Men is absolutely worth the watch, perhaps now more than when it originally hit theaters.

Mystery, Alaska

Maybe this is just on the list because I’m a hockey fan, but Russell Crowe’s underdog film has always been one of my favorites. They capture the feel of a small town, the return of a prodigal son, and a group of guys playing semi-organized hockey in wonderful ways. It builds on the often-debated concept of whether a cohesive group of amateurs could defeat a professional team by extending the discussion to how it would affect not only those who are directly involved, but also what it does for the town and its traditions. Maybe it only resonates with sports fans, but that’s enough to keep it from being just an Honorable Mention.

Office Space

I’m terrible at quoting movies, but this film has quite a few lines that I immediately recognize when someone recites them. In fact, many of the lines and concepts have become so much of a part of our culture that many people might not even realize this is where they’re from. Mike Judge has proven himself to be a comedic genius, and Office Space goes a long way towards making his case. I’ve never looked at a stapler the same way after seeing this. If you have a desk job or are a server at a restaurant, this is a “Must See” for sure.


As a life-long fan of comic books and superheroes, the idea of vigilante justice has always been something that I’ve been inclined to support as a means to solving issues that law enforcement can’t. This revenge thriller is easily one of my top five Mel Gibson movies, as it mixes in enough dark humor and fun dialogue to go along with the action.

The Talented Mr. Ripley

I’ve always been of the opinion that Matt Damon is a very talented actor, and this movie pairs very nicely with Good Will Hunting to show his range in serious roles. This is one of those films with such good performances, interesting plotlines, awesome filming locations and is crafted in such a high quality manner that I got myself a copy to watch at home as soon as it was available, introducing as many other people to it as I could. Now more than 20 years later, I guess I’m trying to do that again. I can’t speak to how well it has held up, although I’ll be making a point of watching it again soon now that it’s back on my mind. Regardless, I’m certain that this isn’t a risky recommendation.

The Boondock Saints

I remember being sooooo excited to introduce my friends to this movie that I saw on campus my first semester at college, but tracking down a copy proved to be a difficult task back then. For whatever reason, The Boondock Saints didn’t have great distribution, but I eventually got a copy and my friends were certainly glad that I did. The performance by Willem Dafoe takes an otherwise good movie and makes it great. The level of violence involved makes it something that won’t suit everyone’s tastes, but it’s one of those films that I just love watching.

The Hurricane

By the time Denzel Washington starred in The Hurricane, he didn’t need the help of a strong performance in this biopic to prove what he was capable of doing. He had already shown how great he was in the likes of Glory, Malcolm X, and Philadelphia (just to name a few). This film was meaningful to me because it was in the phase of my life where I was starting to actively pay attention to what actors were bringing to roles instead of just getting immersed in the film, as well as seeking out movies to help broaden my understanding of the human condition and films that introduced the notion that there are societal evils that exist that many people aren’t aware of (myself, specifically, included). I’m not sure whether I had heard the Bob Dylan song about boxer Rubin Carter before I saw the movie, but if I had, I certainly didn’t understand it (and its implications) until I saw this movie. While I think unfair treatment of minorities by law enforcement is something that movies and television shows are bringing to the forefront more today than they did 20 years ago, I think this film certainly serves as a good example of mistreatment and inequality as it brings to light a true story that many might not be aware of otherwise.

The Sixth Sense

There are some movies that deserve an immediate re-watch the moment the first viewing is over, and The Sixth Sense might have been the first time I encountered such a movie. I’m typically not a fan of scary movies, and while many people might scoff at the notion that I’d consider The Sixth Sense “scary”, there were certain moments in it that were a bit frightening the first time I saw it, and even during re-watches, they’re still moments where I’ll look at the corner of the screen to lessen their impact. This movie is likely one that most people know the plot twist for, even if they haven’t seen it, but it’s such a well-crafted movie that re-watching it while knowing the twist is actually a more enriching experience. I won’t give away the twist for anyone who has avoided it thus far, because it’s quite an experience to watch it, get the plot twist, and then watch it all over again and see it in a different way.

The Thomas Crown Affair

He’s not my favorite actor in the role of James Bond, but if I’m honest with myself, I enjoy the work of Pierce Brosnan more than I probably give him credit on first consideration. But in the remake of The Thomas Crown Affair, he might be perfectly cast. Maybe it’s because I’m a fan of painter Rene Magritte, whose artwork is prominently featured in the film, or maybe it’s the chemistry between Brosnan and Rene Russo, but I really liked this movie. Perhaps not nearly as iconic as some of the films in the Honorable Mentions section, it’s also less prominently discussed and thusly more likely that people haven’t heard of it or seen it yet than some of the films I didn’t include.

Honorable Mentions

American Pie

Teenagers in the late 90s and early 2000s undoubtedly heard about American Pie, even if their parents wouldn’t let them see it. I don’t know how many sequels this movie spawned, or how many quotable lines it has, but if you’re talking about iconic coming-of-age comedies, this was probably the top of the list for that era.

South Park: Bigger, Longer & Uncut

This movie just continued to build the case for the genius of Trey Parker and Matt Stone, as the South Park juggernaut took to the big screen. It took the form of a satirical musical that was so good that its script convinced George Clooney to join in the list of actors who voiced characters in the film.

Notting Hill

One of my wife’s favorite movies, the storyline between Hugh Grant and Julia Roberts makes for a decent movie, but what I enjoy most about this film is the roommate character played by Rhys Ifans. His total commitment to a zany, grimy, uncultured, completely non-self-aware housemate just steals the scenes he’s in.

The Green Mile

This Stephen King novel adaptation was nominated for Best Picture and had some very memorable performances, big and small. It essentially made the career of Michael Clarke Duncan, though would probably rank low on the list of Tom Hanks roles.

The Insider

Currently the highest-rated film from 1999, the biopic featuring Russell Crowe got a few Academy Award nominations, including Best Picture and Best Actor, but no wins. While I usually like movies from Crowe and Director Michael Mann, this one wasn’t memorable enough for me to include it on the main list.

Wild Wild West

While this futuristic-but-somehow-a-bit-steampunk Will Smith and Kevin Kline sci-fi had some fun moments, the only reason I even mention this movie is because of some trivia I learned a few years back. Kevin Smith almost wrote and directed a Superman movie, but folks at Warner Bros provided notes on the storyline on how they envisioned the movie. Their notes, as relayed by Kevin Smith in a Q&A session that made it to YouTube, were core elements of what years later would become the movie Wild Wild West.

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