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It's A Wonderful Life (1946)
Despite its cheerful rep, the holiday season can be a tough time of year. Who better to watch than Jimmy Stewart as the down-in-the-dumps George Bailey realizing things might not be so bad, after all? Though new versions in color have been released, we vote for the old-school black and white.
He'll love: The catchy 1940s lingo.
You'll love: Mary and George are so in love they donate their honeymoon cash to townspeople in need and stay home instead.