Even though he was known for being an Actor before he got into politics, Ronald Reagan was never exactly an A-list movie star. Heck, the only movie I've ever heard that he was in was Bedtime for Bonzo (at least I think that was the title), and I don't think it was movie gold.
So, your challenege, is to have Ronald Reagan win an Academy Award (aka, an Oscar) for either Best Actor or Best Supporting Actor. POD must be between 1940 and 1963. Bonus points if you can also have him win an award later for Best Director.