I'm going with Reese Witherspoon and Jake Gyllenhaal. Not that this has to be about couples, but I think it would be an interesting change for each of them as she always plays the good-girl/southern belle and he some type of wonder boy.

Vivian Ward -- Anne Hathaway
Edward Lewis -- Patrick Dempsey
Kit DeLuca -- Lindsay Lohan
Phil Stuckey -- Jeremy Piven

**I REALLY wanted to cast Spencer Pratt as Stuckey, but I figured reality TV "star" didn't count for this! Britney Spears could also pull off Kit

Vivian-- Kiera Knightley

Edward-- Joshua Jackson

Philip the sleazy lawyer--Jack Black

Kit--Anne Hathaway

Bernard--Sacha Baron Cohen

Vivian (Evangeline Lilly)
Edward (Eric Bana)
Kit (Rose Mcgowan)
Philip (Jeremy Piven)
Bernard (William Fichtner)

Oops, I forgot Bernard...how could I forget him?!

Vivian Ward -- Anne Hathaway
Edward Lewis -- Patrick Dempsey
Kit DeLuca -- Linday Lohan
Phil Stuckey -- Jeremy Piven
Bernard -- Jack Nicholson (I think he'd spice it up!)

Other Possibilities

Vivian (Amanda Peet)
Edward (George Clooney)
Kit (Ali Larter)
Philip (Julian McMahon)
Bernard (Tony Shalhoub)

Vivian: Angelina Jolie
Edward: Brad Pitt
Kit: Christina Applegate
Phillip: Philip Seymour Hoffman
Bernard: Tim Russ (of Samantha Who and Star Trek)

I had to had to cast Jolie and Pitt for the amazing chemistry. Their dance in Mr and Mrs Smith would be nothing next to the piano scene. Plus we know Angelina looks hot in hooker boots (Mr/Mrs Smith)

I love that Hoffman can play such a slimy guy and Tim Russ does a fantastic job of playing a reserved, polished guy.

Vivian – Sandra Bullock
Edward – Patrick Dempsey
Kit – Jennifer Esposito
Philip – Matt Dillon
Bernard – Morgan Freeman

Nothing beats the original!

vivian: isla fisher
edward: patrick dempsey
kit: drea de matteo
phillip: paul giamatti
bernard: hugh laurie

Vivian-- Kate Hudson/Natalie Portman

Edward-- Harrison Ford/Dennis Quaid

Philip--John Cusack/Christian Slater

Kit--Elisha Cuthbert/Elizabeth Berkeley

Bernard--Tim Curry (a shoe in, just check him out!)

Vivian (Julia Roberts)--Ali Larter
Edward (Richard Gere)--Shia LaBeouf
Kit (Laura San Giacomo)--Rachel Bilson
Philip (Jason Alexander)--Hayden Christenson
Bernard (Hector Elizondo)--Queen Latifa (I know in the movie it's a man, but I just see the queen as being very helpful!)

My spelling is off today, sorry! And sorry about the linking of R.Bills and Hayden, but I put them in and just noticed it! They would be great--they don't even see each other in the movie anyway.

Vivian=Anne Hathaway (she's proven she does the make-over princess thing well, and she was pretty impressive in Havoc)

Edward=I think John Cusak could be interesting as Edward. Sort of like if Lloyd Dobler had grown up and sold out. Vivian could reignite that iconoclastic spark.

Kit=Brittany Murphy. Can't you just hear her saying "Cinder-*bleeping*-rella"?

Philip=Jeremy Piven. Especially fun because he and Cusak used to be really good friends, and then apparently had some kind of falling out.

Bernard=Dunno why, but I'd really like to see Edward Herrmann in this role.

Vivian- Scarlet Johanson
Edward- Viggo Mortenson
Kit- Lindsay Lohan
Philip- Billy Bob Thorton
Bernard- Matthew Broderick

Billy Bob would make such a goof sleazy lawyer, and you know Scarlet could pull this off.

Vivian - Rachel McAdams
Edward - Patrick Dempsey
Kit - Sienna Miller
Phillip - Jeremy Piven
Bernard - Billy Crystal

Vivian - Jenna Fischer
Edward - Paul Judd
Kit - Britney Spears (she already has the slutty boots)
Philip - Jack Black
Bernard - George Lopez

Vivian- Rachael McAdams
Edward- Ben Affleck
Kit- Jennifer Esposito
Philip- Clive Owen
Bernard- Robin Williams

Vivian - Rachel McAdams
Edward - Brad Pitt
Kit - Sarah Michelle Gellar
Philip - Peter Sarsgaard
Bernard - Stanley Tucci

Vivian = Lauren Graham
Edward = Ben Affleck
Kit = Taryn Manning
Philip = Kevin Nealon
Bernard = Terry Kinney

Vivian- Katie Holmes
Edward- Tom Cruise
Philip- Jack Black
Kit- Hayden Pannetierre
Bernard- Matthew Modine

Vivian - Rachel McAdams
Edward - Clive Owen
Kit - Tessa Thompson
Philip - Philip Seymour Hoffman
Bernard - Michael Caine

Vivian - Jamie-Lynn Sigler
Edward - Christian Bale
Kit - Brittany Murphy
Philip - Patton Oswalt
Bernard - Larry David

No one could ever fill Julia's, hooker boots.

Vivian (Julia Roberts)--Ali Larter
Edward (Richard Gere)--Shia LaBeouf
Kit (Laura San Giacomo)--Rachel Bilson
Philip (Jason Alexander)--Hayden Christenson
Bernard (Hector Elizondo)--Queen Latifa (I know in the movie it's a man, but I just see the queen as being very helpful!)

My spelling is off today, sorry! And sorry about the linking of R.Bills and Hayden, but I put them in and just noticed it! They would be great--they don't even see each other in the movie anyway.

i'll go with this.lol

That's a hard one! No one could ever replace Julia in Pretty Woman!

Vivian (Julia Roberts)- Kate Hudson
Edward (Richard Gere)-- George Clooney
Kit (Laura San Giacomo)-- Christina Applegate
Philip (Jason Alexander)--Jeremy Piven
Bernard (Hector Elizondo)-- Gary Senise

Vivian - Mandy Moore
Edward - Dermot Mulroney
Kit - Jessica Biel
Phillip - Kevin Bacon
Bernard - Willie Garson (Stanford from SATC)

I re casted 2 ways one with original story and the second with a twist like he meets her in Compton instead of Beverly Hills but keep the sweet charm it has by keeping director Garry Marshall!

Vivian - Zooey Deschanel or Keri Russell /Joy Bryant
They all are different in their movie choices,but I know they could all pull it off!

Edward - James Franco or Joseph Gordon-Levitt /Common All 3 of those actors would do a great job! Common seems like such a gentleman and I could see him being tormented about his father and his feelings for him!

Kit - Zooey Deschanel she is great at quirky characters if being Vivian doesn't work out OR Britney Murphy /Jessica Alba OR Rosario Dawson Jessica and Joy can switch up a bit a bit since in Honey Jess was the lead and Joy was the funny friend!

Phillip - Josh Hartnett I would like to see josh play a role where he is mean /Jeremy Piven(both) is great at being dirty sleazebags with alterior motives ,He could be in the original and the twist and he and Common are buddies!

Bernard - Hugh Dancy someone British should play the nice guy who helps her out /Andre 3000 I just could see him being helpful and funny!

Vivian: Megan Fox
Edward: Ethan Hawke

Vivian -Mary Kate Olsen
Edward - Jude Law
Kit - Natalie portman
Philip - Michael Cera
Bernard - Steve Martin

Vivian-Linday Lohan
Edward-Tom Cruise
Kit-Emily Blunt
Philip-Jeremy Piven
Bernard-Stanley Tucci

Vivian - Rachel McAdams
Edward - George Clooney
Kit - Selma Blair
Philip - Paul Giamatti
Bernard - Hugh Laurie

Vivian- Anne Hathaway
Edward- Patrick Dempsey
Kit- Brittany Murphy
Philip- James Spader
Bernard- Tony Plana (The dad from Ugly Betty)

Vivian - Meghan Fox
Edward - Hugh Grant or Clive Owen
Kit - Zooey Deschanel
Philip - Jack Black, David Spade, or Jeremy Piven
Bernard - Willie Garson

Vivian - Reese Witherspoon in brunette
Edward - Rupert Everett
Kit - Marisa Tomei
Philip - Jack Black
Bernard - Paul Giamotti

Vivian: Scarlet Johansson
Edward: Hugh Jackman
Kit: Rosario Dawson
Philip: Paul Giamatti
Bernard: Rupert Everett

Vivian (Julia Roberts) - Kate Bosworth
Edward (Richard Gere) - Clooney!
Kit (Laura San Giacomo) - Rhianna (the singer)
Philip (Jason Alexander) - Will Arnett
Bernard (Hector Elizondo) - the janitor from Scrubs

My Pretty Woman Recast:

Vivian (Lauren Graham)
Edward (Patrick Dempsey)
Kit (Kristin Chenowith)
Philip (Vince Vaughn)
Bernard (Hector Elizondo)

Vivian: Keira Knightley
Edward: Clive Owen
Kit: Maya Rudolph
Philip: Philip Seymor Hoffman
Bernard: Anthony Hopkins

I've got to entries. And I didn't look at other ideas before posting mine so here i GO!

Entry 1:
Vivian: Anne Hathaway
Edward: Ben Affleck
Kit: Kierston Warren (Alex from saved by the bell the college years)
Phillip: Jeremy Piven
Bernard: Victor Garbur

Entry 2:

Vivian: Reese Witherspoon
Edward: Casey Affleck
Kit: Heather Matarrazzo (Lily form princess diaries)
Phillip: Patrick Dempsey (I really think that he could play a really good a-hole effectively)
Bernard: Victor Garber

fyi, victor garbur(garber?) is dad from Alias.

Vivien: Elisha Cutbert
Edward: Daniel Craig
Kit: Emily Blunt
Phillip: Michael Keaton
Bernard: Stanley Tucci

Cymone, nice one on bringing in Danieal Craig. he is fiercely sexy. mmmmmmmm.

Vivian (Sophia Bush)
Edward (Johnny Depp)
Kit (Rachel McAdams)
Philip (Jeremy Piven)
Bernard (Eric Dane)