While top 10 lists are pretty attainable to keep in your head, it's near impossible to really keep a Top 100 although somewhere in my archives I did tackle the task of trying to create the top 100 films I've ever watched.
I decided recently to try redrafting it, since I've seen many more films and my take on films has changed as I've gone along. The first time I ever made a top 100 list was in 2003 (the cut was a much lowered bar: films like Cool Runnings and Aspen Extreme made it) and because a) it really is hard to squeeze all the new films into 100 and b) films need some time to age, I'm going to go with greatest films up to 2003. A lot of the newer films are just going to surface in the bottom ranks of the list just because comparing classic films and recent films are like apples and oranges.
This entry was tiring and I'm not sure if I'll make it all the way to one even though I have the list written out. Leave comments and click on my links and I might be inspired to continue!
100. Cider House Rules, 1999, dir. by Lasse Holstrom, starring Tobey MaGuire, Michael Caine, Jane Alexander, Charlize Theron, Kathy Baker, Paul Rudd
A beautifully shot coming-of-age period piece that my coworker at Blockbuster made fun of me for liking and that I'm still ashamed to say that I have a lot of reverence for. It's not necessarily a profound film and if Miramax succeeded in getting the film an Oscar win over Dreamwork's American Beauty (fresh off the heels of Saving Private Ryan vs Shakespeare in Love, the two were engaged in a fierce marketing battle) then there might really be reason to hate this film. Nevertheless, it is a good film.
99. You Can Count on Me, 2000, dir. and written by Kenneth Longorean, starring Laura Linney, Mark Ruffalo, Matthew Broderick, John Tenney
I always group this one with "Wonder Boys" and "Almost Famous" as very honest character-driven pieces that came out in the same yaer, and I could easily exchange this with "Almost Famous." It's a film about how little of an adult you feel like when you're in the presence of your adult sybling. Laura Linney plays a "responsible" single mom and Ruffalo plays the "irresponsible" brother coming for a visit. Both characters are full of doubt about themselves in different ways and the way in which these two lost souls intersect on this visit is very moving.
98. 25th Hour, 2002, dir. Spike Lee, starring Ed Norton, Rosario Dawson, Barry Pepper, Philip Seymour Hoffman, Barry Pepper, Brian Cox, Anna Paquin
It's been a somewhat frustrating experience originally liking and championing this film when it first came out and then watching it get praised in retrospect for all the wrong reasons. When publications such as The AV Club, RogerEbert.com, Rolling Stone, Paste Magazine and others came out with Best Films of The Decade list* 25th Hour seemed to come at the top of many of these lists because a lot of people wrongly hailed this film as the definitive cinematic artifact of 9/11. In truth, it has absolutely nothing to do with 9/11 except that Spike Lee filmed it in New York right after the event and you can see the buildings missing in the skyline in the background. I like 25th Hour because it's a film with a great sense of dramatic tension, with the story taking place over just one night, and I think the characters are taken in very interesting directions. It's also very well-acted.
*I don't have the time to look up specifically which ones named it so high. I believe AV Club had it listed at #2 and Roger Emerson of Roger Ebert ran a poll in which 25th Hour placed pretty high for the wrong reasons.
97. Sunshine State, 2002 dir. John Sayles, starring Angela Bassett, Alan Rickman, Mary Steenburgen, Edie Falco, Timmothy Hutton, James McDaniel, Gordon Clapp, Jane Alexander
I love good ensemble films and I love films that have a great sense of place. There's also no place I love more than Florida which is what this film is about. It's about a seaside town is an unrealized slice of paradise to a lot of people. The beachside town has historical significance for the black residents because it represented a civil rights victory enabling them to get a "piece of the beach." From that subpopulation, a woman forced into exile through a teen pregnancy (Bassett) and the much more succesful ex-NFL player who impregnated her are both returning to town because a decision has to be made as to whether to sell their land to make way for a new development. In the meantime, there's a seaquarium mermaid entertainer who's bored to death of living in the same town too long (Falco) and a tightly wound spokeswoman for the new development freaking out that no one's sharing her enthusiasm (Steenburgen) and failing to notice that her husband is repeatedly attempting suicide (Clapp).
96. Our Man Flint, 1966, starring James Coburn, Lee J. Cobb, Gila Gollan
It's difficult to quantify just why this is a great film except by the measure that I've watched it over and over and over and still enjoyed it. It's camp, which I previously wrote (in my post about Glee and the 1960's Batman show) is something you enjoy because it's consciously bad. The film is a parody of James Bond films that is played straight in a way, but is ultimately very silly and I find the film both hillarious and very classy. The actor, James Coburn (Great Escape among other films), was a very slender actor who stood out for me in the films I saw him and like the actor who played James Bond he won an Oscar well after his superhero days. He won in 1998 and was a very pudgy old man when he appeared on the podium to accept*.
*I saw his acceptance speech only in retrospect
95. Birth of a Nation, 1915, dir. by DW Griffith, starring Lillian Gish
This film prompts an interesting debate: It's undoubtedly a historic artifact, being the first major epic, the first silent film to tell a story, the first movie that approached feature length, and a number of other firsts. It's also a very racist and misguided film that helped launch the popularity of the Ku Klux Klan. I omitted this film the last time I made my list but I recently reconsidered because the film has great historical value. More importantly, there's just a certain magic existent in it: you're watching the experience of right and wrong change right from under your eyes.
94. Catch Me If You Can, 2002 dir. by Stephen Spielberg, starring Leo DiCaprio, Tom Hanks, Christopher Walken, Amy Adams, Martin Sheen, Jennifer Garner, Ellen Pompeo
I thought it was a great time capsule and one of many great examples of how Spielberg's films are always solid stories that rarely dissapoint. Beware, there are always a lot of Spielberg haters out there.
Link to a review
93. X-Men 2, 2003, dir. by Bryan Singer, starring Patrick Stewart, Ian McKellan, Famke Jannsen, Hugh Jackman, Brian Cox, Alan Cumming, Halle Berry, Shawn Ashmore, James Marsden, Anna Paquin, Kelly Hu, Rebecca Rojmain
I wasn't a comic book geek growing up. Of the few superhero series I was exposed to as a kid, X-Men was one of my enthusiastic favorites and I was delighted to see the cartoon (or rather the comic) translated cinematically so well. X-Men 2 was superior to the first in working the kinks out. I've enjoyed the scientific bent, the realistic modern tone, the sleek visuals and the great special effects. Most importantly, the cast is incredible.
92. Evita 1996 dir. Alan Parker, starring Madonna, Antonio Banderas, Jonathan Pryce
I remember watching this in a movie theater when I was in 8th grade. I was in my third year of Spanish and I have always had an interest in Latin Ameircan culture and history (I later took courses on Latin American history and geography in college) but I was dissapointed with this film because they almost never spoke. I didn't know the difference between a musical (songs interspersed with dialogue) and an opera (all songs) back then. This film has grown a lot more on me in subsequent viewings. One of the few Non-Disney musicals to be made in the 25 or so years prior to the genre's return with "Moulin Rouge" and "Chicago", this film wins me over for its great musical numbers and because it's rich in historical context. Although it's merely song and dance, the film has almost as much to say about the period as a history textbook.
91. To Kill a Mockingbird, 1962 dir. Robert Mulligan, starring Gregory Peck, Robert Duvall, Mary Badham, Phillip Alford
I was struggling with placement here and whether to put this at all. The film is ranked 58th on imdb and it's on the AFI top 100, so others haven't hesitated to list this as a classic. My brief conflct, aside from taking up a space on the list, was that the book (which I've personally read) itself is a masterpiece. Is this just something to watch if you're too lazy to read the book? I think in this case, the performances elevate it. Gregory Peck competed against Peter O'Toole of "Lawrence of Arabia" and won at the Oscars, and it was because he took an iconic figure and made it his own (O'Toole did the same thing too, to be fair). I also do like a good courtroom drama (even though I detest lawyers and being in court).
90. Master and Commander, 2003 dir. Peter Weir, starring Russell Crowe, Paul Bettany
In a way, this movie is the best historical epic I've ever seen because even though it doesn't serve the story, it serves history. For example, in a story set in the Napoleonic Wars on the high seas (where every minute of this film takes place) we would naturally be looking forward to seeing exciting naval battles amd while we do get our share of exciting naval action, we mostly experience the HMS Surprisespending their time waiting and trying to maintain their sanity so that when a battle actually does come, you realize the magnitude of it. The human element of the movie, the multi-layered friendship between Russell Crowe and Paul Bettany, doesn't disspaoint either
89. Wait Until Dark, dir. Terrence Young, starring Audrey Hepburn, Alan Arkin
Audrey Hepburn is such a sweet, precious concoction that it's hard to imagine her in a thriler. That is, it's hard to imagine anyone wanting to kill her. In "Charade" (which also makes my list), the villains are so quirky and (even cute in a Looney Tunes kind of way) that you never really feel like she's in danger. Wait Until Dark is a great thriller that really does push that line. The film is also very minimalist in its use of space. Audrey Hepburn plays a blind women and the film takes place almost entirely in her apartment. As the audience, we are privy to more than she is and are given the point of view of the villains. A pair of thieves willing to kill for a valuable stash of trafficked drugs in Hepburn's possession. With their mark being blind, they set up their ruse in our plain sight. It's a brilliantly suspenseful film
88. Gangs of New York, 2002 dir. Marty Scorsese, starring Leo DiCaprio, Daniel Day-Lewis, Cameron Diaz, Liam Neeson, Jim Broadbent, John C Reilly, Brendan Gleason, Gary Lewis