Lelaina: Rachel Bilson
Troy: James Marsden
Vickie: America Ferrara
Michael: T.R. Knight
Sammy: Shia LaBeouf

Lelaina Pierce: Alexis Bledel
Troy Dyer: James McAvoy
Vickie Miner: America Ferrara
Michael Grates: Matthew Rhys
Sammy Gray: Shia LaBeouf

Hi,

Here are my picks:

Lelaina Pierce (Winona Ryder) - Evan Rachel Wood
Troy Dyer (Ethan Hawke) - Shia LaBeouf
Vickie Miner (Janeane Garofalo) - Anna Paquin
Michael Grates (Ben Stiller) - Adam Brody
Sammy Gray (Steve Zahn) - Emile Hirsch

Lelaina: Thora Birch
Troy: Ryan Gosling
Vickie: Maggie Gyllenhaal
Michael: Milo Ventimiglia
Sammy: Kerr Smith

Lelaina Pierce: Lindsay Lohan
Troy Dyer: Shane West
Vickie Miner:Sandra Oh
Michael Grates: Adam Brody
Sammy Gray: Seth Green

Lelaina Pierce (Winona Ryder) - Kirsten Dunst (with her boho style, she can pull off the brilliant slacker, all indecisive about men and future)
Troy Dyer (Ethan Hawke) - Chad Michael Murray (he can definitely do scruffy bad boy)
Vickie Miner (Janeane Garofalo) - Amber Tamblyn (she's got that great sarcastic voice for this caustic character)
Michael Grates (Ben Stiller) - Adam Brody (looks like a lot of people had the same idea!)
Sammy Gray (Steve Zahn) - Joseph Cross (he was the lead in Running with Scissors, he could definitely pull off the sensitive best friend role)

Lelaina Pierce - Samaire Armstrong
Troy Dyer - Shia LeBeouf
Vickie Miner - Christina Ricci
Michael Grates - Milo Ventimiglia
Sammy Gray - Zachary Levi or Michael Cera

leaina- sarah michelle gellar (prinze)
troy- ryan gossling
vickie- mandy moore
micheal- justin long
sammy- daniel radcliffe

Lelaina Pie - Zooey Deschanel
Troy Dyer - Danny Masterson
Vickie Miner - Liza Weil
Michael Grates - Devon Gummersall (Brian Krakow all grown up)
Sammy Gray - Joseph Gordan-Levitt

no idea, but i loved this movie! "tempted by the fruit of another..." i think of this movie everytime i hear that song. and how hot was ethan hawke in this

Lelaina Pie - Natalie Portman
Troy Dyer - Justin Bobby from The Hills
Vickie Miner - Ellen Page
Michael Grates - Christopher Gorham from Ugly Betty
Sammy Gray - Ben Foster

Lol @ Justin Bobby playing Troy. Wait, no, that could work. JB reminds me of a disgusting pig version of a good friend of mine and Troy is basically the same person as a good friend of mine. Haha.

BTW, I LOVED this movie.

ok i didnt look at any other comments so i wouldnt be influnced

winona - zooey descanel
ben - Milo ventimiglia
ethan - shia lebeuff
jeanine - sara silverman
steve - seth rogan

winona - keira knightley (has anyone seen The Jacket?)
ben - jake gyllenhaal
ethan - ryan philippe
jeanine - sara silverman
steve - zach braff

Lelaina Pierce--Natalie Portman
Troy Dyer--Ryan Gosling
Vickie Miner--Zooey Deschanel
Michael Grates--Jake Gyllenhaal
Sammy Gray--Zac Efron

This is going to be a hard one......the original cast was perfecto.

Lelaina Pierce (Natalie Portman)
Troy Dyer (Adrian Grenier)
Vickie Miner (Zooey Deschanel)
Michael Grates (Adam Brody)
Sammy Gray (Andy Samberg)

Again, I didn't look at anyone else's before posting...

Lelaina Pierce - Selma Blair
Troy Dyer - Hayden Christiensen
Vickie Miner - Zooey Deschanel
Michael Grates - Milo Ventimiglia
Sammy Gray - Justin Long

Lelaina Pierce (Courtney Cox)
Troy Dyer (David Arquette)
Vickie Miner (Tina Fey)
Michael Grates (Adam Sandler)
Sammy Gray (Elijah Wood)

Lelaina Pierce (Winona Ryder)- Marisa Tomei
Troy Dyer (Ethan Hawke)- Jude Law
Vickie Miner (Janeane Garofalo)- Salma Hayek
Michael Grates (Ben Stiller)- Adam Sandler
Sammy Gray (Steve Zahn)- Hugh Jackman

Ok - here goes:
Vickie - Rumer Willis
Michael - Ryan Philippe
Sammy - Seth Rogan
Lelaina- Natalie Portman
Tory - John Mayer

Lelaina Pierce (Anna Faris)
Troy Dyer (Heath Ledger)
Vickie Miner (Amber Tamblyn)
Michael Grates (Ben Foster)
Sammy Gray (Michael Cera)

Lelaina Pierce (Ellen Page)
Troy Dyer (Emile Hirsch)
Vickie Miner (Alia Shawkat)
Michael Grates (Zachary Levi)
Sammy Gray (Paul Dano)

Lelaina Pierce (Chyler Leigh)
Troy Dyer (Shia LaBeouf)
Vickie Miner (Amber Tamblyn)
Michael Grates (Adam Brody)
Sammy Gray (Michael Cera)

Rachel Blison-Leliani
Emile Hirsch-Troy
Zooey Deschanel-Vickie
Milo Ventimiglia-Michael
Elijiah Wood- Sammy

Lelaina - Rachel McAdams
Troy - James McAvoy
Vickie - Maggie Gyllenhal
Michael - Ryan Gosling
Sammy - Emile Hirsch

I tried to pick people that haven't been mentioned yet:

Lelaina Pierce - Kate Bosworth
Troy Dyer - James Franco
Vickie Miner - Chloe Sevigny
Michael Grates - Mark Ruffalo
Sammy Gray - Peter Sarsgaard

Lelaina Pierce (Natalie Portman)
Troy Dyer (Josh Hartnett)
Vickie Miner (Sarah Gilbert)
Michael Grates (Jason Schwartzman)
Sammy Gray (James Franco)

Actually, I want to switch Jason as Sammy and James as Michael

BTW. Justin Bobby...HILARIOUS.

Lelaina Pierce (samaire armstrong)
Troy Dyer (Ryan Gosling)
Vickie Miner (Zooey Deschanel)
Michael Grates (Milo Ventimiglia)
Sammy Gray (Zach Braff)

Leilani Price-Evan Rachel Wood
Vicki Miner-Zooey Deschanel
Troy Dyer-Skeet Ulrich
Micheal Grates-Paul Rudd
Sammy Gray-Luke Wilson

Lelaina Pierce (Emily Mortimer)
Troy Dyer (Jason Bateman)
Vickie Miner (Amy Poehler)
Michael Grates (Thomas Gibson)
Sammy Gray (Paul Adelstein)

I really liked that film, especially the passage when U2's All I Want is You starts playing. Still sends shivers down my spine!

Lelaina Pierce- Natalie Portman
Troy Dyer- Heath Ledger
Vickie Miner- Mandy Moore
Michael Grates- Adam Brody
Sammy Gray-Jake Gyllenhal