2014 happens to be a good year for movies. It is not because there have been a ton of quality flicks released so far, but because it's the 15 year anniversary for 1999 films and the 20 year anniversary for movies released in 1994. In my opinion, 1994 and 1999 are the two best years for film for those in Generation X. We're going to start this two part series looking back 15 years to 1999. I was only going to do 9 movies, but '99 was too good of a year to limit myself to that little of a number. So now, here are the 19 best films of 1999.
19) Toy Story 2
Directed By: John Lasseter, Ash Brannon, & Lee Unkrich
Starring: Tim Allen & Tom Hanks
STARS: 3 out of 4
Brief Description: Even the worst Toy Story is still pretty good.
18) The Talented Mr. Ripley
Directed By: Anthony Minghella
Starring: Matt Damon, Jude Law, & Gwyneth Paltrow
STARS: 3 out of 4
Brief Description: After being sent to Italy to bring home Dickie Greenleaf (Law) to his father, Tom Ripley (Damon), a lying sociopath, forces his way into Greenleaf's inner circle. And get this, bad things erupt. Dum, dum, DUUUUUUMMM!
17) Mystery Men
Directed By: Kinka Usher
Starring: Ben Stiller, William H. Macy, & Hank Azaria
STARS: 3 out of 4
Brief Description: Before The Dark Knight and Spider-Man creating superhero movies that took themselves too seriously, we had Mystery Men. After Captain Amazing (Greg Kinnear) rids the entire city of bad guys, he unwittingly lets Casanova Frankenstein (Geoffrey Rush) loose, forcing a pack of superheroes with no real powers to save the day.
16) Galaxy Quest
Directed By: Dean Parisot
Starring: Tim Allen, Sigourney Weaver, & Alan Rickman
STARS: 3 out of 4
Brief Description: A surprisingly smart and funny satire about life for actors after starring in geek project like Star Wars or Star Trek. Don't let "starring Tim Allen" fool you, Galaxy Quest is full of fun and laughs. I promise.
15) Lock, Stock, & Two Smoking Barrels
Directed By: Guy Ritchie
Starring: Jason Flemyng, Dexter Fletcher, & Jason Statham
STARS: 3 out of 4
Brief Description: I unfortunately saw Snatch before I saw Lock Stock; therefore, I think Snatch is far superior and Lock Stock is just alright. I know that's unfair to Guy Ritchie's debut, but that's the way the cookie crumbles. Still doesn't decrease the quality of Lock Stock as a whole, just in reference to ranking Guy Ritchie's films.
14) American Pie
Directed By: Paul Herz
Starring: Jason Biggs, Chris Klein, & Seann William Scott
STARS: 3 out of 4
Brief Description: Amidst the sophomoric humor and a dude shtupping a pie is a modern high school movie that will forever be a part of our cultural zeitgeist.
13) Big Daddy
Directed By: Dennis Dugan
Starring: Adam Sandler, Joey Lauren Adams, & Cole and Dylan Sprouce
STARS: 3 out of 4
Brief Description: Remember when Adam Sandler had the ability to not only make a film that made us laugh, but also managed to be sweet and endearing? Yeah, it's been awhile. One could even say it's been 15 years...
12) Eyes Wide Shut
Directed By: Stanley Kubrick
Starring: Tom Cruise & Nicole Kidman
STARS: 3 out of 4
Brief Description: Stanley Kubrick set out to make the best film in every genre. The best horror movie (The Shining), best science fiction movie (2001: A Space Odyssey), the best war movie (Full Metal Jacket), etc, etc. Eyes Wide Shut is easily the most artfully done porno flick ever made. In all seriousness, it's a great sexual thriller that only a director as great as Stanley Kubrick can make.
11) The Boondock Saints
Directed By: Troy Duffy
Starring: Sean Patrick Flanery, Norman Reedus, & Willem Dafoe
STARS: 3.5 out of 4
Brief Description: If there have ever been any imitators of Quentin Tarantino in the past 20 years, it's Troy Duffy. While he may be an obnoxious and insufferable asshole as seen in the documentary "Overnight", Troy Duffy is certainly an extremely talented director as seen by The Boondock Saints. It's just a shame his ego got in the way of making more movies.
10) American Beauty
Directed By: Sam Mendes
Starring: Kevin Spacey, Annette Bening, & Thira Birch
STARS: 3.5 out of 4
Brief Description: While it didn't deserve to win Best Picture at the Academy Awards in the midst of one of the deepest years in cinema of the past 50 years, it's still a great film about the Modern American society.
9) Magnolia
Directed By: John Lasseter, Ash Brannon, & Lee Unkrich
Starring: Tim Allen & Tom Hanks
STARS: 3 out of 4
Brief Description: Even the worst Toy Story is still pretty good.
Directed By: Anthony Minghella
Starring: Matt Damon, Jude Law, & Gwyneth Paltrow
STARS: 3 out of 4
Brief Description: After being sent to Italy to bring home Dickie Greenleaf (Law) to his father, Tom Ripley (Damon), a lying sociopath, forces his way into Greenleaf's inner circle. And get this, bad things erupt. Dum, dum, DUUUUUUMMM!
Directed By: Kinka Usher
Starring: Ben Stiller, William H. Macy, & Hank Azaria
STARS: 3 out of 4
Brief Description: Before The Dark Knight and Spider-Man creating superhero movies that took themselves too seriously, we had Mystery Men. After Captain Amazing (Greg Kinnear) rids the entire city of bad guys, he unwittingly lets Casanova Frankenstein (Geoffrey Rush) loose, forcing a pack of superheroes with no real powers to save the day.
Directed By: Dean Parisot
Starring: Tim Allen, Sigourney Weaver, & Alan Rickman
STARS: 3 out of 4
Brief Description: A surprisingly smart and funny satire about life for actors after starring in geek project like Star Wars or Star Trek. Don't let "starring Tim Allen" fool you, Galaxy Quest is full of fun and laughs. I promise.
Directed By: Guy Ritchie
Starring: Jason Flemyng, Dexter Fletcher, & Jason Statham
STARS: 3 out of 4
Brief Description: I unfortunately saw Snatch before I saw Lock Stock; therefore, I think Snatch is far superior and Lock Stock is just alright. I know that's unfair to Guy Ritchie's debut, but that's the way the cookie crumbles. Still doesn't decrease the quality of Lock Stock as a whole, just in reference to ranking Guy Ritchie's films.
14) American Pie
Directed By: Paul Herz
Starring: Jason Biggs, Chris Klein, & Seann William Scott
STARS: 3 out of 4
Brief Description: Amidst the sophomoric humor and a dude shtupping a pie is a modern high school movie that will forever be a part of our cultural zeitgeist.
Directed By: Dennis Dugan
Starring: Adam Sandler, Joey Lauren Adams, & Cole and Dylan Sprouce
STARS: 3 out of 4
Brief Description: Remember when Adam Sandler had the ability to not only make a film that made us laugh, but also managed to be sweet and endearing? Yeah, it's been awhile. One could even say it's been 15 years...
Directed By: Stanley Kubrick
Starring: Tom Cruise & Nicole Kidman
STARS: 3 out of 4
Brief Description: Stanley Kubrick set out to make the best film in every genre. The best horror movie (The Shining), best science fiction movie (2001: A Space Odyssey), the best war movie (Full Metal Jacket), etc, etc. Eyes Wide Shut is easily the most artfully done porno flick ever made. In all seriousness, it's a great sexual thriller that only a director as great as Stanley Kubrick can make.
Directed By: Troy Duffy
Starring: Sean Patrick Flanery, Norman Reedus, & Willem Dafoe
STARS: 3.5 out of 4
Brief Description: If there have ever been any imitators of Quentin Tarantino in the past 20 years, it's Troy Duffy. While he may be an obnoxious and insufferable asshole as seen in the documentary "Overnight", Troy Duffy is certainly an extremely talented director as seen by The Boondock Saints. It's just a shame his ego got in the way of making more movies.
Directed By: Sam Mendes
Starring: Kevin Spacey, Annette Bening, & Thira Birch
STARS: 3.5 out of 4
Brief Description: While it didn't deserve to win Best Picture at the Academy Awards in the midst of one of the deepest years in cinema of the past 50 years, it's still a great film about the Modern American society.
9) Magnolia
Directed By: Paul Thomas Anderson
Starring: Tom Cruise, Philip Seymour Hoffman, Julianne Moore, John C. Reilly, & Jason Robards
STARS: 3.5 out of 4
Brief Description: Very few directors are able to tell multiple stories with many more characters within a single film. But Paul Thomas Anderson is not like most directors. Even with a cast as huge as Magnolia, P.T. Anderson still manages to create wonderful three dimensional characters. He even managed to pull an Oscar nominated performance from Tom Cruise.
8) Being John Malkovich
Directed By: Spike Jonze
Starring: John Cusack, Cameron Diaz, & Catherine Keener
STARS: 3.5 out of 4
Brief Description: Only a film written by Charlie Kaufman and directed by Spike Jonze is allowed to be as messed up yet wonderful as Being John Malkovich is. Craig Schwartz (Cusack) finds a hidden portal that allows a person to spend 15 minutes inside the brain of character actor John Malkovich. Plus, it's great to see Diaz and Keener play against type and play roles clearly written for the other.
7) Fight Club
Directed By: David Fincher
Starring: Brad Pitt, Edward Norton, & Helena Bonham Carter
STARS: 3.5 out of 4
Brief Description: While I absolutely love David Fincher's movies, I think I might be the only person in Generation X to think Fight Club is pretty good, but not great. I actually think the twist at the end ruins the movie (don't believe me, check out this scene below and re-watch the entire movie like that), but I also refuse to discount how great the first 95% is as well.
6) Dogma
Directed By: Kevin Smith
Starring: Linda Fiorentino, Matt Damon, Ben Affleck, Jason Lee, Alan Rickman, Chris Rock, Jason Mewes, & Kevin Smith
STARS: 3.5 out of 4
Brief Description: Classic Jay and Silent Bob film but with philosophical debates about Jesus Christ and organized religion. Plus, it's great to see Matt Damon and Ben Affleck going on a murderous rampage before the Bourne flicks and Argo. "Was Wisconsin really that bad?" Yes. Yes it is.
5) Office Space
Directed By: Mike Judge
Starring: Ron Livingston, Jennifer Aniston, & Gary Cole
STARS: 3.5 out of 4
Brief Description: I don't care that Office Space plays on Comedy Central every other weekend. The multiple viewings doesn't diminish how amazing this comedy is. We've all been stuck in a dead end job and how inadequate we feel. Only the mind behind King of the Hill and Beavis and Butthead can make this mundane topic brilliant.
4) The Green Mile
Directed By: Frank Darabont
Starring: Tom Hanks, Michael Clarke Duncan, & Sam Rockwell
STARS: 3.5 out of 4
Brief Description: After John Coffey (Duncan) is sentenced to death for alleging killing two little girls, prison guard Paul Edgecomb (Hanks) must do his best to free Coffey from prison. Frank Darabont just has a knack for not only releasing great films, but doing so amidst great years. First, The Shawshank Redemption in 1994, and The Green Mile in '99.
STARS: 3.5 out of 4
Brief Description: After John Coffey (Duncan) is sentenced to death for alleging killing two little girls, prison guard Paul Edgecomb (Hanks) must do his best to free Coffey from prison. Frank Darabont just has a knack for not only releasing great films, but doing so amidst great years. First, The Shawshank Redemption in 1994, and The Green Mile in '99.
Directed By: M. Night Shyamalan
Starring: Bruce Willis, Haley Joel Osment, & Toni Collette
STARS: 4 out of 4
Brief Description: It's easy to dismiss the quality of The Sixth Sense 15 years later considering the horrible turn for the worst that M. Night Shyamalan's career has taken. However, this film is absolute brilliant. The use of red in every shot, the legitimate sense of suspense Shyamalan sets up, and the twist at the end actually makes the film better (unlike Fight Club and every other Shyamalan film).
Directed By: Trey Parker
Starring: Matt Stone, Trey Parker, & Isaac Hayes
STARS: 4 out of 4
Brief Description: Not only is the South Park movie one of the greatest comedies of all time, it's one of the best animated films of all time, and, IMHO, the best musical of all time. Who knew all those pesky restraints like the F.C.C. and only having 6 days to create a product were holding Matt Stone and Trey Parker back.
Directed By: Andy & Lana Wachowski
Starring: Keanu Reeves, Lawrence Fishburne, & Carrie-Anne Moss
STARS: 4 out of 4
Brief Description: On my old site, we did a list of the 25 Greatest Movies of the Past 25 years. The Matrix ended as #2 on the list. I wrote much more on this topic back then than I ever could fit in this little blurb. And probably much more eloquently as well. The Matrix is not only just a fun blockbuster popcorn flick, it's the greatest science fiction film ever made.
Refused to Consider
- Girl, Interrupted
- Star Wars, Episode I: The Phantom Menace
- The Virgin Suicides
- Star Wars, Episode I: The Phantom Menace
- The Virgin Suicides
Ones I Haven't Seen
- Election
- For The Love of the Game
- Iron Giant
- Iron Giant
- Run Lola Run
- Sweet and Lowdown
- The Blair Witch Project
- The Insider
- Three Kings
- The Blair Witch Project
- The Insider
- Three Kings
- Varsity Blues
What Do You Think Is The Best Film of 1999?
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