My little bro would say his are Jingle all the Way and How the Grinch Stole Christmas
All of my guy friends love A Christmas Story and The Muppet's Christmas Carol
Some are attached to Home Alone 1, 2, or 3
and others love Smoky Mountain Christmas, Christmas in Connecticut or While You Were Sleeping
Each year my family watches White Christmas and Holiday Inn and there are probably quite a few I'm forgetting.
I like all of those (bar a couple), but the two very best Christmas movies of all time, the ones I watch every year and pine after and am ALWAYS uplifted by and want my children and their children's children and their children's children's children to watch, are Mr. Kreuger's Christmas and It's a Wonderful Life. Always tear-jerking, always life changing. Try it. I promise you'll like it.
Yes, they both feature Jimmy Stewart. Very astute observation you. And yes, it's true, we are bosom friends. We're going to be neighbors in Heaven. But that's not why I love these. They're just amazing, that's why.