Let me please again state this is a clearly hypathetical cast, I know we all fear a live inaction of ANYTHING anime being a flop like Dragon ball or Air Bender, but lets look at my cast in the eyes of knowing that were this made it would be by a brilliant director who could actually make a live action set of movies work, and a lot of them in sequence like the Harry Potter movies as that is the only way i could see the movies working to include all these characters.
Down to business...
This is a cast according to Shippuden's story arc that will be over several movies long understandably.
For Naruto Uzumaki, I choose Alexander Ludwig
For Sasuke Uchiha-
Thomas Dekker
For Sakura Haruno- Hayden Panettiere
For Kakashi Hatake- Ryan Renolds
For Rock Lee Boo-Boo Stewart
For Gai Sensi- Jackie Chan (Shut up, you know it makes sense)
For Shikamaru- Josh Hutcherson
For Captain Yamato- Ioan Gruffud
For Sai- I choose Matt Dallas from Kyle XY
For TenTen, no she has no last name, I choose Emily Osment
For Hinata- Emily Browning
For lady Tsunade- I choose Christina Hendricks
For the Third Hokage- Nathaniel Lees from Matrix Reloaded, and other movies where he's the wise old guy
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For Orochimaru- Johnny Depp or Christian Bale
For Kabuto- Joseph Gordon Levitt (hey if he's willing to stoop for G-I-Joe, he can do a fricking Naruto movie)
Gaara- Elijah Wood.
The Akatsuki-
Pein- Xavier Samuels
Itachi Uchiha- Ben Barnes
Konan- Anna Kendrick
Deidara- Jamie Cambell Bower
For Kasime I choose Sam Witwer
Took me a while but i chose Alexander Skarsgard as Hidan
And Burn Notices' Jeffory Donovan as Kakuza
Sasori- Cameron Bright