Let’s get one thing out of the way: I love the holidays. I own 19 Christmas albums (from Johnny Cash and Aimee Mann to King's College Cambridge and the early music vocal ensemble Stile Antico) and approximately a gajillion tree ornaments. My family does the traditional Italian Feast of the Seven Fishes on Christmas Eve. And every year, I watch these five movies—my top picks for holiday cheer (and a few heart-warmed tears).
Bing Crosby, Danny Kaye, Rosemary Clooney, and Vera-Ellen team up in this classic featuring possibly the best Christmas song ever written, Irving Berlin’s “White Christmas.” Plenty of singing and dancing, romantic misunderstandings, and a picture-postcard Vermont setting make this one a winner.
Tissue Alert: When Crosby and Kaye’s former WWII Army commander walks into a room filled with veterans who have traveled to pay tribute to him and save his struggling country inn. I’m tearing up at my desk just thinking about it!
Photo: Paramount Pictures
With all due respect to Carrie Underwood, Julie Andrews will always be the one and only Maria. While The Sound of Music isn’t technically a holiday movie, it’s always on TV around Christmas, and the day and the film are inextricably linked in my mind.
Tissue Alert: When the convent’s mother superior sings “Climb Every Mountain,” giving Maria the strength to face her challenges (and her love for her handsome boss). Reprised at the end of the movie as the family flees the Nazis over the Alps into Switzerland, the song is a stirring testament to the power of chasing your dreams.
Photo: Robert Wise Productions
An eight-year-old Natalie Wood plays the skeptical daughter of an equally skeptical divorced Macy’s executive whose suspicion is put to the test by a department-store Santa who claims to be, well, Santa. Standout scene: Santa on trial in a three-piece suit.
Tissue Alert: The finale’s a killer. Natalie Wood gets what she wants for Christmas (hint: it’s much better than a toy) and finally believes.
Photo: Twentieth Century Fox Film Corporation
OK, so it’s not a movie, but it’s still awesome. And almost 50 years on, it still feels contemporary: Charlie Brown complains of holiday depression and the commercialization of Christmas. Fun fact: The show’s director cast kids from his neighborhood to voice several parts—many were so young they couldn’t even read the script.
Tissue Alert: Linus’s rousing speech on the meaning of Christmas (almost cut by TV execs!)
Photo: Lee Mendelson Film Productions
Romantic comedies took a serious nosedive after the 1950s: His Girl Friday and It Happened One Night are some of the genre’s greatest achievements. One big exception: this late ‘80s classic. My friends and I have incorporated so much of the dialogue into everyday speech that I sometimes forget I’m quoting a movie.
Tissue Alert: The dramatic New Year’s Eve closer’s a weeper for sure, but my teariest moment usually happens during one of the segments interspersed throughout the movie featuring real stories of couples.
Photo: Castle Rock Entertainment
Chicago Manual of Style aficionado and college basketball fan Bene loves her a sock bun on days she can't wrangle her curls.