25. Meet Me in St. Louis (1944)
While Vincente Minnelli’s musical is only partially a Christmas movie — covering all four seasons in the run-up to the 1904 World’s Fair — the Christmas segment is one of the most memorable of all holiday movies. Judy Garland makes movie magic by lending her famous vibrato to “Have Yourself a Merry Little Christmas,” a song we know so well, it’s easy to forget it comes from this movie. It’s also the film that introduced Garland to Minnelli, and thus unleashed Liza Minnelli on the world.
Best Scene: A sobbing Tootie beheads a family of snowpeople.
Best Line: “Now I remember where I left my other skate!” –Tootie after Mr. Smith falls down the stairs
24. Die Hard (1988)
What better way to ring in the holidays than with Detective John McClane, a group of terrorists and a ton of explosives on an L.A. highrise? Bruce Willis turned McClane into his career role, while Alan Rickman (Harry Potter) turned terror mastermind Hans Gruber into the AFI’s #46 Greatest Villain. Arguably the biggest action blockbuster of all time, Die Hard is surprisingly covered in holiday spirit, from limo driver Argyle blaring Run DMC’s “Christmas in Hollis” to Reginald Vel Johnson (Family Matters) humming Christmas tunes before a body lands on his windshield. Terrorist Theo also gives his own rendition of “‘Twas the Night Before Christmas,” and “Let it Snow” ushers in the end credits.
Best Scene: Det. John McClane comes out, hands behind his head, gun strapped to his back, ready to “surrender.”
Best Line: “Shoot ‘ze glass.” –Hans Gruber
23. Christmas in Connecticut (1945)
Barbara Stanwyck stars as Elizabeth Lane, a writer famous for her Martha Stewart domestic tips. While claiming to live on a Connecticut farm with her husband and baby, she’s actually a single urbanite without cooking skills. When her boss and a war vet invite themselves up for a nice country Christmas, she’s forced to cover her tracks. Stanwyck’s role was a tame follow-up to her femme fatale in Double Indemnity (1944) and more in line with her comedic deception of The Lady Eve (1941). Shot on the same farmhouse set as Bringing Up Baby (1938) and co-starring Dennis Morgan (Kitty Foyle) and Sydney Greenstreet (The Maltese Falcon), Christmas in Connecticut is one of the real holiday classics of Hollywood’s Golden Age. It was remade in 1992 starring Dyan Cannon and Kris Kristofferson.
Best Scene: Stanwyck falls for Morgan while discussing marriage and children, but can’t act on it because of her little charade.
Best Line: “The things a girl will do for a mink coat.” –Elizabeth Lane
22. Christmas Eve on Sesame Street (1978)
Winner of the Primetime Emmy for Outstanding Children’s Program, this Sesame Street TV special is a classic. Big Bird worries when Oscar the Grouch tells him Santa can’t fit down the chimney; the gang performs a skating rink chain whip; Bert and Ernie fret over getting eachother the perfect gifts; and Kermit and Grover do their best Cosby and Linkletter with a series of kids saying the darndest things.
Best Scene: The Cookie Monster tries writing a letter to Santa, but devours his typewriter.
Best Line: “I’m freezing my giblets.” –Big Bird
21. Bad Santa (2003)
From Big Bird to “flipping the bird,” we move now to the other side of the naughty-and-nice list. Bad Santa is a profanity-laced, booze-drenched, sexed-up romp. And by that I mean it’s hilarious. Billy Bob Thornton earned a Golden Globe nomination as a sleaze-bag shopping mall Santa who hates his job and reluctantly mentors a troubled, pudgy kid. He leads a stellar supporting cast, including Lauren Graham, Sarah Silverman, Tony Cox, the late Bernie Mac and the late John Ritter (in his last role). Not for the easily offended, the film features plenty of “no they didn’t” moments, including a sex scene that puts “I saw mommy kissing Santa Claus” to shame.
Best Scene: The Kid accidentally cuts his hand while making Willie a gift and screams bloody murder.
Best Line: “Should I fix you some sandwiches?” –The Kid