1. "Swingers" - This movie is Money! My favorite movie all time. Reminds me of the friendships I have made in my life and keeps hope alive on me finding that special girl, just like Mikey.
2. "Almost Famous" - This movie is just plain amazing. Cameron Crowe is the most talented man in show business today. Billy Crudup, Kate Hudson, Patrick Fugit, and Jason Lee were all wonderful in this movie. Although I wish William would have ended up going to Morocco with Penny Lane.
3. "The Shawshank Redemption" - This movie is a masterpiece. Tim Robbins and Morgan Freeman. I never saw it until about 3 or 4 months ago and it went right to my favorites list.
4. "Forrest Gump" - Tom Hanks... "Hi my name is Forrest Gump", do I really need to say anything more? Hanks is one of the best actors of our time and Robert Zemeckis is one of the greats of all time. This movie encompasses every emotion possible and cannot be restrained to one single genre.
5. "Gladiator" - Russell Crowe kicked ass. Ridley Scott (brother of Tony Scott) sure as hell knows what he is doing when it comes to movie making.
6. "Jerry Maguire" - Tom Cruise, my favorite actor, Cuba Gooding Jr. saying, "Show me the money!" Cameron Crowe showing the life of a high price sports agent that hits the wall and learns how to be a man.
7. "Rush Hour" - Jackie Chan and Chris Tucker work flawlessly together to create what I consider the funniest move I have ever seen. Jackie Chan is a great martial arts actor.
8. "Braveheart" - Mel Gibson portraying my follow Scottsman William Wallace. Mel Gibson also Directed and was a Producer for the screenplay. I think I want to have the same type of cloth band thing at my wedding like they did back then. I just think it's cool.
9. "The Matrix" - Talk about special effects! In the words of Keanu Reeves, "Woah!" This movie introduced the world to CGI (I know it really didn't, but with how many people saw it you could said it really did.). Lawrence Fishburn was great in this movie.
10. "Notting Hill" - Probably my favorite "chick flick", I love Julia Roberts (oh how I would love to marry her). I don't care what anyone says I like Hugh Grant, that guy is funny in a dry British sorta way.
11. "Office Space" - For anyone that has ever worked in an Office Building (especially for larger companies) you know this movie. It is your life! Mike Judge (from Beavis and Butthead fame) Wrote, Directed and Produced this classic. Ron Livingston of Swingers fame stars. Look supporting actor Diedrich Bader of The Drew Carey Show fame.
12. "Saving Private Ryan" - The greatest war movie I have ever seen. Steven Spielberg made it feel like you were actually there. Tom Hanks once again shows why he's one of the best in the business.
13. "Better Off Dead" - John Cusack as a teenager has to deal with his girlfriend dumping him among family crises, homicidal paper boys, and a rival skier. Not to mention a mom that is trying to learn to cook! Green bacon!?!? John is another of my favorite actors.
14. "Lock, Stock, and Two Smoking Barrels" - Guy Ritchie sure knows what he is doing. This is a guys movie. Everything that can go wrong goes wrong, but it all works out in the end. Funny fact, Vinnie Jones who plays Big Chris, first came to public notice as a professional footballer, playing in the English Football League. Noted as one of soccer's hard men, he leapt to fame when a photographer at a match snapped him "marking" Newcastle United's Paul Gascoigne by grabbing his testicles.
15. "The Princess Bride" - Cary Ewles and Mandy Patinkin make Rob Reiner's fairytale classic one of the most memorable movies of the 80s and one of the favorite films of any female that grew up in the 80s. Saying you like this movie to a girl gives you a big gold star, not to mention this movie is great!
16. "The Wedding Singer" - Watching this Adam Sandler classic makes you think you are watching a movie from the 80s. Drew Barrymore is extra cute and Steve Buscemi making a quick performance all make this Sandler's best movies to date.
17. "There's Something About Mary" - Just like the title states, Mary is the perfect girl, she loves football, is beautiful, and likes food on sticks. Ben Stiller is a comic genius and Matt Dillon plays the perfect slimeball to ruin his attempt to be with his dream girl from high school.
18. "Wayne's World" - Before Mike Myers was Austin Powers he was Wayne. Wayne and Garth are the two funniest characters from Saturday Night Live ever to grace film. Tia Carrere makes me happy to be a man.
19. "Can't Hardly Wait" - I don't care what anyone says this is my favorite teen comedy of all time. Plus I had to have an appearance from Jennifer Love Hewitt, if I didn't you people would have thought that I may have had some issues.
20. American Pie - This movie was hilarious, plain and simple. Yes it was a little over the top, but it's one of the funniest movies of the late 90s. Shannon Elizabeth in all her splendor is an added bonus.
21. "Rushmore" - An offbeat, dark comedy, with a heart. Jason Schwartzman plays the perfect overachieving/geek/loser. Wes Anderson is one of the great new movies makers of my generation.
22. Good Will Hunting - No listing is complete without the greatest dramatic performance by Robin Williams. Matt Damon and Ben Affleck came of age in Hollywood with a terrific film.
23. Days of Thunder - Another great Tom Cruise flick. Robert Duvall is great as his crew chief. Tony Scott shows that he is just as talented as his brother Ridley with one of my favorite sports movies of all time.
24. Clerks - This is the movie that put Kevin Smith on the map. Probably one of the greatest dialog pieces of the 90s. Film in black and white. I can't believe they actually played hockey on the roof!
25. Chasing Amy - Joey Lauren Adams (or is that Renée Zellweger?), Ben Affleck, and Jason Lee are some of the future of Hollywood. Every guy dreams of turning a Lesbian straight... right?
26 High Fidelity - John Cusack playing a guy that is afraid of commitment and tends to be pretty picky when it comes to women (sounds like myself almost). Not to mention the movie of all time favorite lists...
27. Fight Club - "I am Jack's smirking revenge." Edward Norton Jr. and Brad Pitt work wonderfully together. This movie is very deep. You need to watch it a couple times to really understand what is going on.
28. "Overnight Delivery" - This is a hidden gem that I think very few people have seen. Reese Witherspoon with her natural brown hair (oh soooo cute). Paul Rudd who plays Wyatt Trips suspects his girlfriend who goes to another college is cheating on him, so he sends her a letter, but then he finds out he's wrong and has to stop the letter from arriving.