Citizen Kane - William Randolph Hearst & Marion Davies The Godfather - Frank Sinatra & Harry Cohn Dr. Strangelove - Werhner Von Braun & Curtis LeMay Monty Python & the Holy Grail - King Arthur & Sir Lancelot MASH - Douglas MacArthur Patton - George S. Patton
A cougar commentary for that scene from 24 season 2.
"So there I am, and, er... I'm walking stealthily - that's not my normal stealthy walk, it's a special stealthy walk, 'cause I know, I know, right, that Kim Bauer's in the area, I can smell her stupidity, as she so blithely steps into my trap. ...There, she did it, the fool! The absolute fool! Ha-ha!"
Something that I think lots of you forget is that many stars have or had very little to say about a certain film, especially the classics. Remember that back in the studio days actors produced films on a virtual assembly line, so film assignments rarely differed from one to another. Historically actors have been much more effective doing featurettes than whole commentaries. It is mainly the directors that have interesting commentary on films. A recent example is on Finian's Rainbow. While Coppola had a fascinating discussion about cinematography, studio heads, editing, and the script, I doubt that Petula Clark could have talked about anything more than the dancing.
This falls under the category of technically possible, but extremely unlikely...
I really enjoy Oliver Stone's commentary on JFK. He backs up his point of view, is engaging, and relates a lot of good production information, anecdotes, and personal philosophy. I think a fascinating counterpoint to his commentary would be one with scholars who support the Lone Gunman view. Perhaps someone who can defend the technical aspects of the case, and someone else who can critque the portrayal of Garrison and the trial.
I know this will never happen, but I think it would be fascinating...