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Besides the rumored Dave Chappelle cameo, Chris Rock was the original choice for Kovaks and Robert Redford was the original choice for Shaw. Redford turned down the role while Rock lost out to Stiller.
The alternate ending - Instead of ending on a bittersweet note as Josh starts his jail term for the successful heist, safe in the knowledge that everyone else wasn't charged & Shaw's going to spend the last years of his life in prison; originally the film was going to end on a more upbeat note, as the film skipped forward to Josh' release, where Slide would be waiting to return the favor for Josh picking him up from jail the last time he was released, and the front bumper of Josh's car replaced with Shaw's solid gold one. The scene would then cut to Lester's bar, in Shaw's former penthouse, where the staff of the Tower were waiting to celebrate his release, and the implication that he was going to go on that date with Denning after all.