The Best Holiday Entertainment Ever

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Dana Edelson/NBC/NBCU Photo Bank via Getty Images; Everett Collection

’Tis the season to hunker down with Christmas and Hanukkah classics. We’ve made our list and checked it twice — now it’s up to you to vote for your absolute holiday favorite at the end of this gallery.

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15. "The Chipmunk Song," The Chipmunks (1958)

Amid the deluge of similar-sounding yuletide music, Alvin, Simon, and Theodore’s vinyl debut distinguished itself by winning three Grammys and hitting No. 1 on Billboard.

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14. A Christmas Memory, by Truman Capote (1956)

CSU Archives/Everett Collection

Capote’s short story about a 7-year-old boy and his friendship with his elderly female cousin will fill every chamber of your heart.

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13. The O.C.’s “The Best Chrismukkah Ever” (2003)

Fox

In the show’s first season, Seth Cohen (Adam Brody) merged his parents’ two faiths to create “the greatest super-holiday known to mankind,” celebrated with “eight days of presents, followed by one day of many presents.”

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12. The Best Man Holiday (2013)

Michael Gibson/Universal Pictures

The sequel to the 1999 comedy about a tight-knit group of friends (including Taye Diggs, Morris Chestnut, and Nia Long) delivers a surprising emotional punch that will make you wanna call your loved ones.

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11. How the Grinch Stole Christmas! (1966)

Courtesy Everett Collection

This TV special is both a welcome reminder that it’s okay to feel cranky and a touching, nonpreachy tribute to what Christmas is really about. (Hint: not just roast beast.)

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10. A Charlie Brown Christmas (1965)

CBS

Nothing inspires more heartfelt nostalgia than the opening trills of the Vince Guaraldi Trio’s “Christmas Time Is Here.” Charlie and the gang’s search for the meaning of Christmas adds to the old-school delight.

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9. Elf (2003)

New Line Cinema

Will Ferrell sleighs as Santa’s six-foot-tall helper Buddy, who heads from the North Pole to Manhattan to unite with his naughty-listed dad (James Caan) in Christmas’ most quotable movie.

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8. “The Hanukkah Song,” by Adam Sandler (1994)

Dana Edelson/NBC/NBCU Photo Bank via Getty Images

Originally performed on SNL’s “Weekend Update,” this holiday song that Jews and non-Jews alike never knew we needed comes complete with shout-outs to David Lee Roth, the Fonz, and Goldie Hawn, among others.

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7, Die Hard (1988)

20th Century Fox/Getty Images

It’s a traditional Hollywood recipe for a holiday tale: an estranged family reunited, carols, a grinchy villain, even climactic “snow.” The bullets and explosions are merely ornaments.

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6. "Christmas (Baby Please Come Home)," by Darlene Love (1963)

Tiffany Rose/Getty Images

Yes, the season is about joy and togetherness, but some of the best holiday songs are blue — like this enduring soul-pop plea.

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5. Rudolph the Red-Nosed Reindeer (1964)

Classic Media

Beyond providing a creation myth for America’s favorite caribou, this special introduced an unforgettable coterie of stop-motion characters like Hermey the elf dentist, Yukon Cornelius, and Burl Ives’ Sam the Snowman.

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4. "Feliz Navidad," by José Feliciano (1970)

Everything is better with a sprinkle of sazón, including Christmas. Bilingual, bicultural, and awfully catchy, this Caribbean-flavored carol deserves a slot on any holiday playlist.

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3. A Christmas Story (1983)

Everett Collection

Sure, it’s an obvious choice, but little Ralphie’s yuletide tribulations are as rewatchable as fudge. Except I didn’t say fudge...

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2. It's a Wonderful Life (1946)

Courtesy Everett Collection

It really says something that a movie that hinges on one man’s suicidal despair has become a Christmas tradition. Frank Capra directs a flawless Jimmy Stewart in this expertly executed masterpiece.

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1. Love Actually (2003)

What other movie so perfectly encapsulates the warm-and-fuzzy-and-frazzled nature of the holidays? Emma Thompson at her most heartbreaking, Hugh Grant at his most charming, the best airport scenes since Casablanca, and a fantastically uplifting finale featuring the other best part about the holidays — Mariah Carey’s magnum opus “All I Want for Christmas Is You.”

Replay gallery

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The Best Holiday Entertainment Ever

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15. "The Chipmunk Song," The Chipmunks (1958)

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14. A Christmas Memory, by Truman Capote (1956)

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13. The O.C.’s “The Best Chrismukkah Ever” (2003)

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12. The Best Man Holiday (2013)

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11. How the Grinch Stole Christmas! (1966)

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10. A Charlie Brown Christmas (1965)

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9. Elf (2003)

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8. “The Hanukkah Song,” by Adam Sandler (1994)

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7, Die Hard (1988)

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6. "Christmas (Baby Please Come Home)," by Darlene Love (1963)

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5. Rudolph the Red-Nosed Reindeer (1964)

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4. "Feliz Navidad," by José Feliciano (1970)

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3. A Christmas Story (1983)

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2. It's a Wonderful Life (1946)

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1. Love Actually (2003)

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