1) Paul Newman in Somebody Up There Likes Me
Dean was going to play Rocky Graziano in Somebody Up There Likes Me for MGM. He died. Paul Newman stepped in instead. Newman became such an individual star that it's often forget he was very much in Dean's shadow for a long time, playing a lot of similarly moody young men. Like Dean, he was also under contract to Warners. Every role Newman played in the late 50s you could imagine being played by Dean.
2) John Kerr in The Corn is Green
In 1955 just before Dean died it was announced Maurice Evans was negotiating with Dean to star in The Corn is Green for TV with Judith Anderson. He was about to start rehearsals when he died. Kerr took the part - Anderson's role ended up being played be Eva La Galliene.
3) Dewey Martin in The Battler
Martin took over a role meant to Dean in The Battler on TV.
4) Paul Newman in The Left Handed Gun
Apparently Dean was going to be in this. Sounds like a perfect fit. Unlike the first three this may have more been in the "advanced talks" phase. Dean would have made a Western, inevitably. Even Brando did one.
5) Tony Perkins in Fear Strikes Out
This was in negotiation apparently not a done deal. The role would be perfect for Dean - moody young man, athlete, TV origins.
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