This was originally slated to be a top 25. That was until I started thinking of more and just couldn’t decide. I just kept increasing it until I finally landed on 40. Kind of random, but who cares? This is my blog. I do what I want. A couple of fun facts about the list before we dive in.
- Most Featured Decade: 90s
- Most Featured Actors: Leonardo DiCaprio, Tom Hanks, Robert De Niro (4 Appearances)
- Two Trilogies Featured (I cheated and slotted them as one but again, it’s my blog)
40. Heavyweights
Starring: Tom McGowan, Aaron Schwaryz, Shaun Weiss, Tom Hodges, Leah Lail, Paul Feig, Keenan Thompson, David Bowe, Max Goldblatt, Robert Zalkind, Patrick LaBrecque, Jeffrey Tambor, Jerry Stiller, Anne Meara, Ben Stiller
Director: Steven Brill
Released: 1995
Favorite Character: Lars (Tom Hodges)
Favorite Quote: “Don’t pee in the water. Don’t drink the water. He peed in it.”
39. Scent of a Woman
Starring: Al Pacino, Chris O’Donnell
Director: Martin Brest
Released: 1992
Favorite Character: Lt. Colonel Frank Slade (Al Pacino)
Favorite Quote: “I don’t know if Charlie’s silence here is right or wrong, I’m not a judge or jury. But I can tell you this he wont sell anybody out to buy his future! And that my friend is called integrety, thats called courage! Now that’s the stuff leaders should be made of.”
38. Fast Times At Ridgemont High
Starring: Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Phoebe Cates, Brian Backer, Robert Romanus, Ray Walston
Director: Amy Heckerling
Released: 1982
Favorite Character: Jeff Spicoli (Sean Penn)
Favorite Quote: “Hey, wait a minute, there’s no birthday party for me in here.”
37. Blood Diamond
Starring: Leonardo DiCaprio, Jennifer Connely, Djimon Hounsou, Michael Sheen, Arnold Vosloo
Director: Edward Zwick
Released: 2006
Favorite Character: Solomon Vandy (Djimon Hounsou)
Favorite Quote: “Sometimes I wonder, will God ever forgive us for what we’ve done to each other? Then I look around and I realize… God left this place a long time ago.”
36. A League of Their Own
Starring: Tom Hanks, Geena Davis, Madonna, Rosie O’Donnell, Lori Petty, Jon Lovitz, David Strathaim, Garry Marshall, Bill Pullman
Director: Penny Marshall
Released: 1992
Favorite Character: Jimmy Dugan (Tom Hanks)
Favorite Quote: “There’s no crying! There’s no crying in baseball.”
35. Toy Story
Starring: Tom Hanks, Tim Allen, Don Rickles, Jim Varney, Wallace Shawn, John Ratzenberger, Annie Potts, John Morris, Erik von Detten
Director: John Lasseter
Released: 1995
Favorite Character: Woody (Tom Hanks)
Favorite Quote: “Rooooooar! Were you scared? Tell me honestly.”
34. American Pie 2
Starring: Jason Biggs, Shannon Elizabeth, Alyson Hannigan, Chris Klein, Natasha Lyonne, Thomas Ian Nicholas, Tara Reid, Seann William Scott, Mena Suvari, Eddie Kaye Thomas, Eugene Levy
Director: James B. Rogers
Released: 2001
Favorite Character: Steve Stiffler (Seann William Scott) & Paul Finch (Eddie Kaye Thomas)
Favorite Quote: “I’ll get you a spoon so you can eat my ass.”
33. Draft Day
Starring: Kevin Costner, Jennifer Garner, Denis Leary, Frank Langella, Sam Elliot, Ellen Burstyn, Chadwick Boseman
Director: Ivan Reitman
Released: 2014
Favorite Character: Sonny Weaver Jr. (Kevin Costner)
Favorite Quote: “Vontae Mack No Matter What”
32. Rudy
Starring: Sean Astin, Ned Beaty, Charles S. Dutton, Lili Taylor, Robert Prosky
Director: David Anspaugh
Released: 1993
Favorite Character: Rudy (Sean Astin)
Favorite Quote: “Having dreams is what makes life tolerable.”
31. Mean Girls
Starring: Lindsay Lohan, Rachel McAdams, Tim Meadows, Ana Gasteyer, Amy Poehler, Tina Fey
Director: Mark Waters
Released: 2004
Favorite Character: Mr. Duvall (Tim Meadows)
Favorite Quote: “Oh my god! Danny DeVito, I love your work.”
30. Billy Madison
Starring: Adam Sandler, Bradley Whitford, Josh Mostel, Bridgette Wilson, Norm McDonald, Darren McGavin
Director: Tamra Davis
Released: 1995
Favorite Character: Billy (Adam Sandler)
Favorite Quote: “Rizzuto is not a word. He’s a baseball player. You’re cheating.”
29. The Sandlot
Starring: Tom Guiry, Mike Vitar, Patrick Renna, Chauncey Leopardi, Marty York, Brandon Adams, Grant Gelt, Shane Obedzinski, Victor DiMattia, Denis Leary, Karen Allen, James Earl Jones
Director: David Mickey Evans
Released: 1993
Favorite Character: Squints (Chauncey Leopardi)
Favorite Quote: “Heroes get remembered. But legends never die. Follow your heart kid. You’ll never go wrong.”
28. Remember The Titans
Starring: Denzel Washington, Will Patton, Donald Faison, Nicole Ari Parker
Director: Boaz Yakin
Released: 2000
Favorite Character: Herman Boone (Denzel Washington)
Favorite Quote: “I don’t want them to gain another yard. You blitz all night. If they cross the line of scrimmage, I’ma take every last one ya. You make sure that they remember forever, the night they played the Titans.”
27. Superbad
Starring: Jonah Hill, Michael Cera, Seth Rogen, Bill Hader, Martha MacIssac, Emma Stone, Christopher Mintz-Plasse
Director: Greg Mottola
Released: 2007
Favorite Character: Evan (Michael Cera)
Favorite Quote: “Take off your vest. You look like Aladdin.”
26. Shutter Island
Starring: Leonardo DiCaprio, Mark Ruffalo, Ben Kingsley
Director: Martin Scorsese
Released: 2010
Favorite Character: Teddy Daniels (Leonardo DiCaprio)
Favorite Quote: “Which would be worse – to live as a monster or die as a good man?”
25. Step Brothers
Starring: Will Ferrell, John C. Reilly, Richard Jenkins, Mary Steenburgen, Adam Scott
Director: Adam McKay
Released: 2008
Favorite Character: Brennan Huff (Will Ferrell)
Favorite Quote: “Suppose Nancy sees me coming out of the shower and decides to come on to me. I’m looking good. I got a luscious V of hair going from my chest pubes down to my ball fro. She takes one look at me and says ‘Oh my God. I’ve had old bull. Now I want the young calf.’ Then she grabs me by the weiner.”
24. Tommy Boy
Starring: Chris Farley, David Spade, Bo Derek, Julie Warner, Brian Dennehy, Dan Aykroyd, Rob Lowe
Director: Peter Segal
Released: 1995
Favorite Character: Tommy Callahan (Chris Farley)
Favorite Quote: “WHAT’D YA DO?”
23. Catch Me If You Can
Starring: Leonardo DiCaprio, Tom Hanks, Christopher Walken, Martin Sheen, Nathalie Baye
Director: Steven Spielberg
Released: 2002
Favorite Character: Carl Hanratty (Tom Hanks)
Favorite Quote:
Carl: Well would you like to hear me tell a joke?
Earl: Yeah. Yeah, we’d love to hear a joke from you.
Carl: Knock Knock
Earl: Who’s there?
Carl: Go fuck yourselves.
22. American Gangster
Starring: Denzel Washington, Russell Crowe, Chiwetel Ejiofor, Cuba Gooding Jr, Josh Brolin
Director: Ridley Scott
Released: 2007
Favorite Character: Frank Lucas (Denzel Washington)
Favorite Quote: “You’re either somebody or you’re nobody.”
21. Happy Gilmore
Starring: Adam Sandler, Christopher McDonald, Julie Bowen, Carl Weathers
Director: Dennis Dugan
Released: 1996
Favorite Character: Shooter McGavin (Christopher McDonald)
Favorite Quote: “You could trouble me for a warm glass of shut the hell up.”
20. Training Day
Starring: Denzel Washington, Ethan Hawke, Eva Mendes, Scott Glenn, Cliff Curtis, Dr. Dre, Snoop Dog
Director: Antoine Fuqua
Released: 2001
Favorite Character: Jake (Ethan Hawke)
Favorite Quote: “You gotta be a wolf to catch a wolf.”
19. Sleepers
Starring: Kevin Bacon, Robert De Niro, Dustin Hoffman, Bruno Kirby, Jason Patric, Brad Pitt, Brad Renfro, Minnie Driver, Vittorio Gassman
Director: Barry Levinson
Released: 1996
Favorite Character: King Benny (Vittorio Gassman)
Favorite Quote: (After shooting Nokes in the groin) “Did that hurt, Nokes?”
18. Wedding Crashers
Starring: Owen Wilson, Vince Vaughn, Christopher Walken, Rachel McAdams, Isla Fisher, Bradley Cooper, Jane Seymour
Director: David Dobkin
Released: 2005
Favorite Character: Jeremy Grey (Vince Vaughn)
Favorite Quote: “Not nearly as much as I do with the attire that you have on or just your general point of view towards everybody. But let’s go kill some birds, I’m psyched.”
17. Goodfellas
Starring: Robert De Niro, Ray Liotta, Joe Pesci, Lorraine Bracco, Paul Sorvino
Director: Martin Scorsese
Released: 1990
Favorite Character: Jimmy Conway (Robert De Niro)
Favorite Quote: “Now go home and get ya fuckin shine box.”
16. Tombstone
Starring: Kurt Russell, Val Kilmer, Michael Biehn, Powers Boothe, Robert Burke, Dana Delaney, Sam Elliot, Stephen Lang, Joanna Pacula, Bill Paxton, Jason Priestley, Michael Rooker, Jon Tenney, Billy Zane, Charlton Heston
Director: George P. Cosmatos
Released: 1993
Favorite Character: Doc Holliday (Val Kilmer)
Favorite Quote: Literally every word from Doc Holliday’s mouth.
15. Top Gun
Starring: Tom Cruise, Kelly McGillis, Val Kilmer, Anthony Edwards, Tom Skerritt
Director: Tony Scott
Released: 1986
Favorite Character: Pete “Maverick” Mitchell (Tom Cruise)
Favorite Quote:
Iceman: You can be my wingman anytime.
Maverick: Bullshit. You can be mine.
14. Scream
Starring: David Arquette, Neve Campbell, Courtney Cox, Matthew Lillard, Rose McGowan, Skeet Ulrich, Drew Barrymore
Director: Wes Craven
Released: 1996
Favorite Character: Stu Macher (Matthew Lillard)
Favorite Quote: “See it’s a lot scarier when there’s no motive.”
13. The Goonies
Starring: Sean Astin, Josh Brolin, Jeff Cohen, Corey Feldman, Kerri Green, Martha Plimpton, Ke Huy Quan
Director: Richard Donner
Released: 1985
Favorite Character: Chunk (Jeff Cohen)
Favorite Quote: “The next time we see sky, it’ll be over another town. The next time you take a test, it’ll be in some other school. Our parents, they want the bestest stuff for us. But right now they gotta do what’s right for them, cause it’s their time. Their time, up there. Down here, it’s our time. It’s our time, down here. That’s all over the second we ride up Troy’s bucket.”
12. The Lion King
Starring: Matthew Broderick, James Earl Jones, Jeremy Irons, Moira Kelly, Nathan Lane, Ernie Sabella, Robert Guillaume, Rowan Atkinson, Madge Sinclair, Whoppi Goldberg, Cheech Marin, Jim Cummings
Director: Roger Allers & Rob Minkolf
Released: 1994
Favorite Character: Mufasa
Favorite Quote: “Yes, the past can hurt. But the way I see it, you can either run from it or learn from it.”
11. The Bourne Trilogy
Starring: Matt Damon,
Director: Multiple
Released: 2002, 2004, 2007
Favorite Movie: The Bourne Ultimatum
Favorite Character: Jason Bourne (Matt Damon)
Favorite Quote: “If you were in your office right now we would be having this conversation face to face.”
10. The Godfather Part II
Starring: Al Pacino, Robert Duvall, Diane Keaton, Robert De Niro, Talia Shire, Morgana King, John Cazale, Mariana Hill, Lee Strasberg
Director: Francis Ford Coppola
Released: 1974
Favorite Character: Tom Hagen (Robert Duvall)
Favorite Quote: “Keep your friends close, but your enemies closer.”
9. Dead Poets Society
Starring: Robin Williams, Robert Sean Leonard, Ethan Hawke, Kurtwood Smith, Norman Lloyd
Director: Peter Weir
Released: 1989
Favorite Character: John Keating (Robin Williams)
Favorite Quote: “No matter what anybody tells you, words and ideas can change the world.”
8. The Dark Knight
Starring: Christian Bale, Michael Caine, Heath Ledger, Gary Oldman, Aaron Eckhart, Maggie Gyllenhaal, Morgan Freeman
Director: Christopher Nolan
Released: 2008
Favorite Character: The Joker (Heath Ledger)
Favorite Quote: “Some men just want to watch the world burn.”
7. The Karate Kid
Starring: Ralph Macchio, Noriyuki “Pat” Morita, Elisabeth Shue
Director: John G. Alvidsen
Released: 1984
Favorite Character: Mr. Miyagi (Pat Morita)
Favorite Quote: “Sweep the leg.”
6. Forrest Gump
Starring: Tom Hanks, Robin Wright, Gary Sinese, Mykelti Williamson, Sally Field
Director: Robert Zemeckis
Released: 1994
Favorite Character: Forrest Gump (Tom Hanks)
Favorite Quote: “That’s my boat.”
5. The Departed
Starring: Leonardo DiCaprio, Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, Anthony Anderson, Alec Baldwin
Director: Martin Scorsese
Released: 2006
Favorite Character: Sgt. Sean Dignam (Mark Wahlberg)
Favorite Quote: “I don’t want to be a product of my environment. I want my environment to be a product of me.”
4. The Mighty Ducks Trilogy
Starring: Emilio Estevez, Joshua Jackson, Joss Ackland, Lane Smith, Michael Tucker
Director: Multiple
Released: 1992, 1994, 1996
Favorite Movie: D2
Favorite Character: Gordon Bombay (Emilio Estevez)
Favorite Quote: “Defense. See, unlike scoring, defense never quits, but to play great defense, you need one thing above all else. Confidence. Listen, if you learn nothing else when you’re here, you learn this. All right? ‘Cause it’s not just about hockey. It’s easy to be confident when you have control of the puck. It’s very, very difficult to keep that confidence when you gotta take whatever strange bounces life throws your way. Don’t be careless, but don’t be too careful either. You cannot be afraid to lose. That’s how you gain the confidence to attack the game when the puck isn’t yours. That’s how you attack life even when you think you don’t have any control. And that’s how you play real defense.”
3. The Breakfast Club
Starring: Emilio Estevez, Paul Gleason, Anthony Michael Hall, Judd Nelson, Molly Ringwald, Ally Sheedy
Director: John Huges
Released: 1985
Favorite Character: John Bender (Judd Nelson)
Favorite Quote: “You ought to spend a little more time trying to make something of yourself and a little less time trying to impress people.”
2. Good Will Hunting
Starring: Robin Williams, Matt Damon, Ben Affleck, Stellan Skarsgard, Minnie Driver
Director: Gus Van Sant
Released: 1997
Favorite Character: Will Hunting & Dr. Sean McGuire
Favorite Quote: “If I asked you about love, you’d probably quote me a sonnet, but you’ve never looked at a woman and been totally vulnerable. Known someone that could level you with her eyes. Feelin’ like God put an angel on Earth just for you, who could rescue you from the depths of hell. And you wouldn’t know what it’s like to be her angel, to have that love for her be there forever. Through anything.Through cancer. And you wouldn’t know about sleepin’ sittin’ up in a hospital room… for two months, holding her hand, because the doctors could see in your eyes… that the terms ‘visiting hours’ don’t apply to you. You don’t know about real loss, ’cause that only occurs when you love something more than you love yourself. I doubt you’ve ever dared to love anybody that much.”
1. The Godfather
Starring: Marlon Brando, Al Pacino, James Caan, Richard Castellano, Robert Duvall, Sterling Hayden, John Marley, Richard Conte, Diane Keaton
Director: Francis Ford Coppola
Released: 1972
Favorite Character: Sonny Corleone
Favorite Quote: “Leave the gun. Take the cannoli.”
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