20 Best Movies of the Last 20 Years, Part 1: 20-16
I’ve always struggled when it comes to making a definitive list of my favorite movies of all time (but that doesn’t mean I haven’t done it, here is my current top 100, subject to change). I have a hard time comparing older movies to modern ones. That’s not to say I don’t enjoy movies that were made before I was born or have a hard time with black and white. Most of the classics that I’ve seen are classics for a reason and I like them as such. But when it comes to those older films I tend to rate them more binary for whatever reason. Its either yay or nay. My best guess is that there just isn’t that connection that comes from being alive in the era that a given movie was filmed in. Even with modern period pieces they’re still using current technology and are coming at it from today’s perspective.
Not to mention I just haven’t seen nearly enough movies pre-1987 to feel confident in having a substantial opinion on them. I’m always working to catch up with more of the classics and am open to recommendations on how to go about doing it but usually when I’m trying to pick a movie to watch I’ll lean towards a newer release. There’s only so much time in a day and its hard to keep up when you’re someone like me who tries to simultaneously keep up with new releases and watch highly regarded older movies. So that’s why when the idea for this list came up it made perfect sense for me. I only started to seriously get into film in the early 2000’s and I feel like I’ve seen most important or critically praised movies since then. And 20 years is a nice round number so the movies eligible for this list have to have been released theatrically in the United States after the clock struck 12 on January 1st, 1997. I never know how to distinguish between ‘best’ and ‘favorite’ with these things, I don’t think they’re mutually exclusive when it comes to a personal list such as this.
(Discuss this list and tell me why I’m wrong on the BSL Board here.)
WALL-E (June 27th, 2008)
When I wrote about my ranking of Pixar movies following the release of ‘Finding Dory’ I ranked this at the very top and I stand by it. Here’s what I wrote:
“Not only is WALL-E my favorite Pixar movie, its in my top 5 favorite animated movies of all time and my top 50 favorite movies period. Its not a perfect movie, the last act is a little too conventional and cartoony, but the first half transcends being a movie for kids. The silent film aspect and the relationship at the center of the story are so striking its hard to stop watching if your flipping channels and come across it at that point. In a time of sequels this film stands on its own.“
I’ve seen a lot of animated movies over the course of my life. Obviously most people see a bunch of them as they’re growing up but I kept watching most of the big ones as I got older and now that I have two kids, I pretty much see every one that gets released. There is a lot of mediocrity in the genre, it’s easy to entertain a young person as long as you’re telling hacky jokes and projecting bright colors on the screen. But a great animated movie can bridge the gap and entertain both kids and adults alike. ‘WALL-E’ does this as good or better than any of them. It makes a compelling case that humans will be their own demise while also just being a ton of fun with a couple of great characters.
The Social Network (October 1st, 2010)
Here we have another movie about technology and the changing tide of human behavior, this time centering around the invention of Facebook. Aaron Sorkin adapted the script for this from ‘The Accidental Billionaires: The Founding of Facebook, A Tale of Sex, Money, Genius, and Betrayal’ which was another book that people thought wouldn’t be possible to make into a cohesive movie (see also: Moneyball and Steve Jobs) that ended up being a razor sharp award worthy script. Not to mention one of the best directors in the business, David Fincher, elevated it further with his attention to detail and being able to get the most out of his cast. Great dialogue and character development, the legal proceedings are especially crackling. Not to mention the movie really captured a moment in time with the way Facebook became so ubiquitous, people of all demographics getting hooked on the social networking website. Its a shame the movie lost Best Picture at the Oscars to ‘The King’s Speech’, a very good but safe movie. The fact that Fincher was able to make this story feel like an entertaining thriller while also maintaining a sense of importance is impressive. Jessie Eisenberg was perfectly cast as a smarmy intellectual and the movie also introduced me to Andrew Garfield, Armie Hammer, and Rooney Mara, all good actors in their own right.
The Assassination of Jesse James By the Coward Robert Ford (September 21st, 2007)
As well as having one of the longest titles without a colon in film history this movie caught me off guard as one of the years best in 2007 which is an impressive feat when you take a look at how many great movies came out that year. Its a long movie, almost three hours, that I didn’t have high expectations for when I eventually watched it and ended up being blown away. The thing that stood out for me was the tone and atmosphere that the film conveyed. The cinematography is dark and a little grainy but it works for the realism that director Andrew Dominik is going for. Brad Pitt and Casey Affleck are phenomenal as the title characters respectively and so is everyone in the cast for that matter. They really take you on this epic journey of their relationship from beginning to the bitter end. Dominik digs deep into the character development, really showing you the reasoning behind their actions without beating you over the head with it. The supporting cast includes Sam Rockwell, Sam Shepherd, Jeremy Renner, and Zooey Deschanel. There are scenes from this film seared into my brain they’re so good including the end. You know whats coming based on the title of the movie alone but you know these characters so well you’re really hoping they’ll change their destiny. Its not a movie for everyone but if it sounds interesting and you haven’t seen it beore, definitely check it out. The director of this has only made three movies since he started at the turn of the century but he’s batting 1.000 in my eyes with ‘Killing Them Softly’ and ‘Chopper’ being the other two.
No Country For Old Men (November 9th, 2007)
Speaking of the great year for movies that was 2007, here we have the film that went on to win Best Picture at the Academy Awards. The Coen brothers directed this modern western about a guy played by Josh Brolin who finds a bag of money following a drug deal gone wrong, a monotone terrifying killer looking to recover said money, and an old sheriff who is looking to apprehend said killer. The killer is legendary movie villain Anton Chigurh played by Javier Bardem in an Oscar winning performance. His simple and emotionless murdering gives an immediate sense of danger to any character that crosses his path with a flip of a coin being the only determining factor. The Sheriff is played by Tommy Lee Jones at his ‘get off my lawn’ best while Josh Brolin and Woody Harrelson bring their A game as well. Movies like this and ‘A Simple Plan’ have taught me that if I come across a bunch of cash unexpectedly, let it be. It never ends well. And honestly either does this movie. Instead of going out with a crescendo it ends abruptly following a monologue by Jones. I respect what the Coens were going for but for me its the difference between a great movie that makes the tail end of a list like this and competing for the top spot. Maybe over time and over re-watches I’ll come around to it but for now this is where it stands.
Fantastic Mr. Fox (November 13th, 2009)
I just wrote about how great of an animated film ‘WALL-E’ is for both kids and adults and while I think my 16th favorite movie of the past 20 years doesn’t equal it in that department, its still my favorite animated movie of all time. While I do think most kids would like ‘Fantastic Mr. Fox’ well enough the quirky humor and stop motion animation isn’t as easy of a sell. I’m not always a big fan of Wes Anderson’s movies but his style of film making is perfectly suited for stop motion. Intricate attention to detail and parallel shots galore. His characters are typically cartoonish in nature anyway so of course having George Clooney, Bill Murray, Jason Schwartzman, Willem Dafoe, and Owen Wilson voice the dry wit of the characters here is a perfect fit. Its both the funniest of his cussing movies and I would argue the most impressive visually. The characters here humanized animals and they are a great blend of having the wherewithal of human beings while keeping the base instincts of their species nature. Its a great take on the story of a criminal who takes on “one last job” while also being a good family drama with a central father/son relationship. It’s a bunch of fun and an easy re-watch. I’m hopeful that Anderson will return to stop motion animation at some point in his career.
An auxiliary member of the MMAJA, Bob used to run the baseball blog 'The Oriole Report' before transitioning to podcasting about movies, TV, Video Games, and MMA. 'The Redbox Report' movie podcast was started in 2013 followed by 'The Redbelt Report' MMA podcast in 2016. In 2018 they were merged into 'Phelan to Communicate', a podcast that can be found on iTunes and a blog that can be found at http://PhelanToCommunicate.wordpress.com. Bob has also written for Konsume.com and BaltimoreSportsReport.com and delivers mail for a living in Baltimore County. Follow him on Twitter @PhelanToTweet.