Top 50 Movies Of The Past Twenty Years

Entertainment, Featured — December 5, 2013 at 9:52 pm by

50. Superbad ’07: Hilarious tale of the greatest quest a high school guy ever embarks upon; getting laid. Maybe the most notoriously funny character of this century in McLovin.

49. The Town ’10: Ben Affleck wrote, directed, and starred in this dynamic story of a bank robbing crew from Charleston. The final heist scene at Fenway Park is a classic.

48. Jurassic Park ’93: Spielberg was way ahead of his time as usual in this visual masterpiece. I was 12 when this came out and it scared the shit out me.

47. Vanilla Sky ’01: This story has so many layers and to this day, I’m still not sure how to interpret the ending. Either way, it’s fabulous acting, directing, and cinematography.

46. Titanic ’97: James Cameron’s epic depiction of one of the biggest tragedies of the twentieth century. It was the highest grossing movie in history until being unseated by another Cameron flick about blue aliens.

45. Braveheart ’95: The Mel Gibson epic is bloody, intense, and makes you want you go out and defend something.

44. Sleepers ’96: Great story, great cast, and a look at true justice being done at any cost.

43. 40 Year Old Virgin ’05: Steve Carrell’s first shot at a lead role and he was magnificent. Seth Rogen and Paul Rudd also really catapulted their careers of this movie.

42. The Da Vinci Code ’06: Yes the book was far better, and yes Tom Hanks’ hair looked ridiculous, but Ron Howard still did an excellent job adapting one of the most popular fiction novels of all time.

41. Inglorious Bastards ’09: Quentin Tarantino simply doesn’t make movies that aren’t fantastic. IB is just another example of his genius. In his version of reality, they kill Hitler in a movie theatre!

40. Mystic River ’03: This is a perfect case of superb acting. All three leads, Sean Penn, Tim Robbins, and Kevin Bacon give Oscar worthy performances in this gritty tale about how three childhood friends’ lives come back full circle to intertwine at the tragic murder of one of their daughters.

39. No Country For Old Men ’07: Another Coen Bros classic that pits Josh Brolin against one of cinema’s biggest badass characters Anton Chigurh, played masterfully by Javier Bardem.

38. The Fugitive ’93: Harrison Ford and Tommy Lee Jones are incredible in this instant classic. I’ve literally watched this movie twenty times and it doesn’t get old.

37. American Psycho ’00: This Bret Easton Ellis penned script horrifically comes to life through the performance of then newcomer Christian Bale. I mean who doesn’t secretly want to bang two hookers, film it while showing off your guns to yourself, and then go after the girls with a chainsaw? Patrick Bateman is one of the best characters of this century so far.

36. Knocked Up ’07: By far the best Judd Apatow movie, this movie made bonafide stars of Seth Rogan, Jonah Hill, and even put Paul Rudd on another level.

35. Boogie Nights ’97: Backed by a ridiculously great cast, Boogie Nights tells the story loosely based on John Holmes’ life through the fictional character Dirk Diggler.

34. Bridesmaids ’11: This movie is just fucking funny as shit. Melissa McCarthy steals every scene she’s in, but Kristin Wiig and the rest of the cast are great too. Classic line from Jon Hamm, “You’re no longer my number three!”

33. Scream ’96: Wes Craven brought this instant classic to life. It was absolutely genius to kill off a big star like Drew Barrymore in the first scene. This was one of the best films of the nineties.

32. Avatar ’09: Say what you will about the underlying political messages or whatever, but this film was impressive. Guess it should be for the most expensive movie ever made.

31. Heat ’95: This marked cinematic history as the first time two icons appeared together in a scene. De Niro and Pacino square off as bank robber vs cop in this action packed blockbuster from Michael Mann. If you really appreciate movies then you have to love how they build up this scene between the two heavyweights, which doesn’t even happen until almost two hours into the movie. It’s by far one of the most powerful scenes of the last twenty years.

30. Zodiac ’07: Another David Fincher gem, Zodiac follows the investigation into one of the most notorious unsolved murder cases in American history. Backed by an extremely strong cast, it’s a must see especially if you have little or no knowledge of the Zodiac murders.

29. Anchorman ’04: Will Ferrell is the funniest actor of our generation period. No movie better showcases his talents more than Anchorman.

28. Inception ’10: Christopher Nolan wrote, produced, and directed this mind bending thriller that undoubtedly should have earned him a best original screenplay award. The 37th most successful box office movie of all time, Inception will stand as one of the best and most influential films of this generation.

27. Clerks ’94: Our first look at the comedic genius of Kevin Smith, who wrote, produced, directed, and costarred in the low budget cult classic. Smith financed the movie himself, shot it in black and white, and launched an extremely successful movie career all on the back of the Clerks success.

26. Fight Club ’99: I’m probably going to get bashed for not having Fight Club higher, but it is what it is. Love the movie, obviously love the aforementioned director David Fincher, and the acting is top notch. It’s hard to imagine that Floyd from True Romance has become one of the best actors of the last twenty five years.

25. Boondock Saints ’99: This movie came out of nowhere to become a huge cult classic. It’s a badass in your face thrill ride that’s funny and easy to watch over and over. You have to respect Troy Duffy’s unique storytelling methods, and Willem Dafoe is brilliant as FBI agent Paul Smecker.

24. Almost Famous ’00: Cameron Crowe’s look at an upcoming band dealing with their rising stardom in the early seventies, and the young boy who wrote their story for Rolling Stone magazine. The guy who steals every scene in my mind is Jason Lee, who plays the lead singer who’s constantly overshadowed by the lead guitar player. The best scene is where the band thinks their plane will eminently crash and they spend their last few moments telling each other exactly what they think of each other.

23. The Game ’97: Broken record maybe but this is my second favorite David Fincher movie. The screenplay is phenomenal as it’s one of those movies that you wish you could go back and watch it again for the first time.

22. American Pie Series: The four main installments of the AP franchise are all side splitting hilarious. Jim and his friends are my exact age so maybe that’s why I hold this franchise in higher regard then some, but there is no denying that American Pie was the funniest young comedy since Animal House.

21. Casino ’95: To me Casino was even better than Scorsese’s Good Fellas a few years earlier. The cast was stellar, and the story was much more invigorating. I love Don Rickles as the Casino manager.

20. Cocaine Cowboys ’06: This documentary makes you want to move to Miami, buy an Uzi, and become and cocaine dealer. Ok maybe not but this doc is the most entertaining I’ve ever watched.

19. Dogma ’99: By far my favorite Kevin Smith movie, Dogma is a hilarious light hearted look at how ludicrous some people are over religion. The all-star cast really makes this one of the funniest movies that I’ve ever seen. Alan Rickman is phenomenal as the arch angel Metatron, “You people. If there isn’t a movie about it, it’s not worth knowing, is it?”

18. Social Network ’10: Aaron Sorkin does great job adapting Ben Mezrich’s book about the birth of Facebook and the betrayal of its founders against one another. Jesse Eisenberg is fabulous playing computer genius Mark Zuckerberg, and you will never guess who but David Fincher directed.

17. Old School ’03: My fourth favorite comedy of all time, Will Ferrell, Vince Vaughn, and Luke Wilson star as three regular guys who decide to start a fraternity. It’s hard to go a few weeks without having someone around you reference something from this movie. “You know what, I’ll do one!”

16. Pulp Fiction ’94: Widely considered one of the best films of this generation, Quentin Tarantino genius is unparalleled. His storytelling is unique and fresh, and he presents such a wide variety of interesting characters whose lives all become randomly intertwined. This is the movie that put Travolta’s career back into relevance.

15. Dark Knight Rises ’12: I know I’m much higher on this movie then most, but I came out if the theatre thinking that that was one of the best movies I had ever seen. Tom Hardy had the impossible job of playing the villain following Heath Ledger’s legendary performance as The Joker, and he was spectacular. His performance as Bane blew me away, stealing every scene.

14. The Departed ’06: Martin Scorsese’s look at the corrupt world of the Boston Police force and Mob. All the acting performances were superb from Leo and Damon, all the way down to Alec Baldwin and Mark Wahlberg. And of course Jack was at his best playing Frank Costello. You really have to watch it two or three times to really appreciate how great this movie is.

13. The Hangover ’09: The monster summer hit of 09 may have spawned two bad sequels, but nothing can beat how fucking funny the original is. Zach Galifianakis rightfully shot into stardom after his hilarious performance as Allen, and who can forget baby Carlos!

12. The Oceans Series: All three of these movies were instant classics. From the star studded cast to the extravagant settings, Oceans always delivered in good hearted entertainment (even if it is about a bunch of crooks.). I wish someday I can dress like the guys from the Oceans movies.

11. Any Given Sunday ’99: I’m a huge Oliver Stone fan and outside of JFK (which wasn’t eligible for this list due to its 91 release), Any Given Sunday is my favorite Stone flick. It perfectly encapsulated the state of the NFL at the turn of the century. Stone was able to address so many issues seamlessly in the story from money, contracts, medical morality, media interference, old vs. new, and the idea of constantly evolving in the game of football. Pacino’s speech before the playoff game will be a scene I will hold onto forever.

10. There’s Something About Mary ’98: The Farrelly Brothers hit it big here with Stiller, Diaz, and Dillon. It’s by far the funniest romantic comedy if all time, if that’s how you want to distinguish it. So many great lines and memorable scenes, “how did you get the beans over the frank?” I know I spent the summer of 98 quoting the movie entirely way too often. “No six minute abs, who can work out in six minutes!”

9. LA Confidential ’97: Great script, great cast, and Russell Crowe kicking the shit out of people. Danny DeVito is especially good as the sleazy back alley photographer the feeds the corruption machine that is the LA police department in the 50’s with his candid blackmailing shots. Everyone has a secret and no secret is safe. The only thing it lacked was a good shot of Kim Basinger’s Leinenboobals, you figure she plays a high priced hooker you’re at least privy to some skin but surprisingly no.

8. Seven ’95: Another Fincher masterpiece, Brad Pitt, Morgan Freeman, and Kevin Spacey are all brilliant in this dark thriller. A serial killer is targeting his victims who are violating the seven deadly sins. The movie keeps you on the edge of your seat throughout, and Spacey’s chilling final scene performance was absolutely Oscar worthy.

7. Forrest Gump ’94: If you don’t love this movie then you’re not American. Tom Hanks is at his very best as the slightly slow southern boy from Alabama who always seems to fall up in every endeavor. A completely original script that tells a story that you can’t help but fall for. It’s one of the smartest movies I’ve ever seen.

6. Dumb and Dumber ’94: Also one of the smartest movies I’ve ever seen. Maybe not, but by far the funniest movie I have ever seen. I would love to sit and argue with anybody who doesn’t think this is the greatest comedy movie ever made.

5. Good Will Hunting ’97: Affleck and Damon won a well-deserved Oscar for this amazing screenplay. Robin Williams also was well deserving of his best supporting actor win, as his performance was one of my favorite in any movie I’ve seen. The movie is gritty, smart, funny, and above all entertaining.

4. Saving Private Ryan ’98: I call bullshit if you can tell me that you don’t feel like you’re watching actual combat footage of D-Day. My grandfather stormed the beach, and when he saw the first twenty minutes of the movie, he said it couldn’t have been more real. Watching this movie just amazes me at what they were able to accomplish on screen. This story will hit you deep down in your gut, and you will never forget it.

3. The Dark Knight ’08: This movie will blow you away. It’s hard not to let Heath Ledger’s turn as the Joker take spotlight off the movie as a whole, because it easily can. Ledger, in my mind, portrayed the best villain in cinematic history. The opening heist scene is also one of my favorite action scenes ever. Christopher Nolan took the Batman franchise to an elite level.

2. The Usual Suspects ’95: I was hard pressed not to put this at number one because it’s my favorite movie of the past twenty years. I could watch this crime thriller ten times in a month and never get tired of it. I love every character, it’s funny, exciting, keeps you guessing all the way through the end, and who really is Keyser Soze?

1. The Shawshank Redemption ’94: Widely regarded as one of the greatest movies ever made. No argument here, as everything about Shawshank is excellent. The story, which was based off a Stephen King novel, is captivating. The acting is superb from Tim Robbins and Morgan Freeman, all the way down the cast; I especially enjoyed William Sadler’s performance as Heywood. It’s nearly impossible to make a stronger case for a movie of the past twenty years.


  1. I almost stopped reading when I saw Braveheart at 45. I do like the top 10 though. One of my favorite movies of the last 20 years that is not on there is How to Train Your Dragon. I know animated. It has everything though, the action at the end is as good as anything.

  2. Woops. you spelled ‘Inglorious Bastards’ incorrectly.


  4. How old are you?? 11 years old? So many crap film you input as the best film such as The Tourist, American Pie, Avatar. Blah…. fix it kid….

  5. The worst list i have ever seen in entire my life!!!!

  6. How can braveheart, avatar, and gladiator made the list while lord of the rings not?????

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