I'd chose A Christmas Story.

It's set in Hohman, Indiana in the 1940's where a young boy named Ralphie attempts to convince his parents, his teacher, and Santa that a Red Ryder B.B. gun really is the perfect Christmas gift.

It's especially fun to find hidden local references to Hammond, Indiana - which is the actual town Hohman was based on. The author, Jean Parker Shepherd grew up in Hammond. Shepherd is the narrator in the movie and has a cameo appearance as a man waiting in the Santa line.

Raised in Hammond, Indiana, Jean Shepherd went on to work in the steel mills and was a veteran of the Army Signal Corps before entering the arts. In the 1950s, he began a long career as a radio personality telling stories of his youth, commenting on current topics and performing silly songs.
(snip)
His articles were published in a series of books including "The America of George Ade", "In God We Trust, All Others Pay Cash", "Wanda Hickey's Night of Golden Memories, and Other Disasters", "A Fistful of Fig Newtons" and "The Ferrari in the Bedroom".
(snip)
In 1983, he wrote his first feature film, A Christmas Story (1983), putting together many tales of his semi-autobiographical character "Ralphie". A sequel, "My Summer Story" (aka It Runs in the Family (1994)) was made in 1994.

The reason it's so fun, is that I've lived in and near Hammond for 30 years. Here's a fun fact I just discovered researching the author - he used his middle name as Ralphie's last name in the movie.

Don't worry about trying to find it on TV. They usually have a 24 hour marathon on Christmas Eve or Christmas Day.