'White Christmas,' Frank Sinatra - This quintessential Christmas song was written by Irving Berlin in 1942, and first popularized by none other than Bing Crosby (selling more than 100 million copies). That said, Frank Sinatra and The Drifters both breathed new life into the song, and every version is magical.

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'Let It Snow,' Dean Martin - Although greats like Ella Fitzgerald, Frank Sinatra, and Michael Bublé also recorded the song, the reason it rose to fame was Dean Martin.

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'2000 Miles,' The Pretenders - "I hear people singing / It must be Christmas time." The sweetest, heartbreaking nostalgia is delivered in this '80s track, and when you hear people singing it, you'll know it's time.

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'Little Drummer Boy/Peace On Earth,' Bing Crosby and David Bowie - This rare collaboration between two legendary and iconic artists is a tearjerker in the best way possible.

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'The Chipmunk Song (Christmas Don't Be Late),' Alvin and The Chipmunks - It's the only appropriate time to listen to high-pitched chipmunks singing about hula hoops. Fun fact: this song won three Grammy Awards!

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'Happy Holiday,' Andy Williams - This easy, breezy, holiday tune puts a little skip in everyone's step.

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'O Holy Night,' Josh Groban - Pair one of the most well-known Christmas carols with one of the most beautiful, velvety vibratos in the world, and you've got a hit holiday track. When he starts belting, you can't help but get goosebumps!

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'Happy Xmas (War is Over),' John Lennon and Yoko Ono - The song that reminds everyone that this wonderful season is truly about peace.

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'Silent Night,' The Temptations - The Temptations take the cake, even though Bing Crosby's version is one of the best-selling singles in recorded music history, and both Frank Sinatra and Sinead O'Connor did the song more justice than we could have expected.

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'Rockin' Around the Christmas Tree,' Brenda Lee - If 'Home Alone's' Kevin McCallister thinks this song is worthy of being played at a holiday party, it definitely needs a place on your playlist.

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'Have Yourself a Merry Little Christmas,' Judy Garland - In 1944, Hugh Martin and Ralph Blane co-wrote this song for Judy Garland for the film 'Meet Me in St. Louis.' It's since ranked third on the American Society of Composers, Authors, and Publishers' most performed songs during the Christmas season, and was later re-popularized by Frank Sinatra.

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'Christmastime is Here,' Vince Guaraldi Trio - Charlie Brown and Christmas go hand in hand, and this song is guaranteed to deliver a strong dose of nostalgia.

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'Christmas Canon,' Trans-Siberian Orchestra -

This song somehow captures the sounds of the heavenly gift of holiday spirit descending on the lives of every poor soul.

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'Run Rudolph Run,' Chuck Berry - There's nothing cooler than a rock 'n' roll reindeer! This song amps up a childhood favorite with an early rock star.

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'The Christmas Song (Merry Christmas to You),' Nat King Cole - The song that made you think you needed to roast chestnuts over an open fire even if you've never had them before. Dean Martin and Mel Tormé also deserve a slice of fame for this song, which was actually inducted into the Grammy Hall of Fame in 1974.

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'Rudolph the Red-Nosed Reindeer,' Gene Autry - Gene Autry was the first to record the irresistible Christmas song, and it even climbed to the No.1 spot on the US music charts. Notable covers include jazzed up versions by Ella Fitzgerald and The Temptations.

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'It's the Most Wonderful Time of the Year,' Andy Williams - Recorded by Andy Williams in 1963, this song has only grown in popularity over the years. It has ranked in the top 10 most downloaded and aired songs during the holiday season for nearly a decade.

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'Winter Wonderland,' Michael Bublé - The song was written in 1934 and has been recorded over 200 times by popular recording artists such as Frank Sinatra, Elvis Presley, Tony Bennett, and Kylie Minogue. But the most popular recording today is by the modern king of Christmas, Michael Bublé.

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'Sleigh Ride,' The Ronettes - Just hear those sleigh bells jingling, ring-ting tingling! This upbeat song was popularized by The Ronettes in 1963, and it has charted in the top 10 Billboard holiday songs almost every year since its release.

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'Frosty the Snowman,' Gene Autry - You know all the words, so why not put it on the playlist? If you're looking for a little more swing, check out Jimmy Durante's version.

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'The Little Drummer Boy,' The Jackson Five - Written in 1941 and recorded in 1951 by the Trapp Family Singers, this song has been integral to the Christmas season for many moons. The young voices of the Jackson Five just renewed its spirit.

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'A Holly Jolly Christmas,' Burl Ives - No one could sing it better than this jolly looking man, who actually kind of resembles ol' Saint Nick himself...

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'Do They Know It's Christmas?,' Band Aid - Band Aid was a charity supergroup founded by Bob Geldof and Midge Ure (pictured), formed to raise money for Ethiopia's famine. They created this song that captures the essence of the '80s in such a wholehearted holiday spirit and enlisted the likes of Bono, Duran Duran, Boy George, Kool & The Gang, Phil Collins, and George Michael.

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'Jingle Bells,' Ella Fitzgerald - One of the best-known and commonly sung holiday songs in the world—and the first song broadcast from space in a Christmas-themed prank by Gemini 6 astronauts—feels fresh and exciting with the help of Fitzgerald's sweeping vocals.

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'Twas the Night Before Christmas,' The Four Tops - The Detroit vocal quartet who helped define the city's Motown sound of the '60s is welcomed with open arms into holiday playlists around the world.

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'Carol of the Bells,' Mykola Leontovych - This epic, slightly creepy Christmas carol from 1914 was based on a Ukrainian folk chant but became really popular in the US where it was transformed into a Christmas song, famously featured in the 'Home Alone' soundtrack.

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'We Wish You a Merry Christmas,' Enya - Though the song's origins are not known, Enya's smooth, synthesized rendition, with a hint of harpsichord, gives the childhood classic new life.

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'Deck the Halls,' Nat King Cole - Embrace tradition, yuletide, and New Year's all in one! Nat King Cole's buttery voice is hard to resist.

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'Twelve Days of Christmas,' Bing Crosby and The Andrews Sisters - Recorded way back in 1949, this song has been covered by numerous artists, including Burl Ives, Perry Como, the Sinatra family, and even the Muppets.

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'Merry Christmas Baby,' Otis Redding - You have to throw some '60s R&B into your Christmas playlist!

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'I Saw Mommy Kissing Santa Claus,' The Jackson Five - Though Jimmy Boyd sang it first at age 13, and made it a No.1 hit on the Billboard pop singles, The Jackson Five added the Motown spin this song needed.

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'Here Comes Santa Claus,' Gene Autry - Gene Autry was largely responsible for making Christmas such a musical triumph, allowing artists like Elvis Presley, Doris Day, Bing Crosby, The Beach Boys, Bob Dylan, and even RuPaul to carry the torch.

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'(It Must've Been 'Ol) Santa Claus,' Harry Connick Jr. -

Bring out the childlike glee with this jazzy '90s tune that reminds you what it's like to believe in Santa.

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'All I Want for Christmas Is You,' Mariah Carey -

This song has been a go-to for more than 20 years, blasting its way into the holiday canon and peaking at no.1 on the US 2019 Billboard Hot 100.

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'Last Christmas,' Wham! - Learning from your mistakes and treating your heart with the respect it deserves sounds good year round.

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'The Hanukkah Song,' Adam Sandler - Even if you don't celebrate Christmas, there's an iconic holiday song for you.

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'Christmas (Baby Please Come Home),' Darlene Love - This epic song was also covered by Bono, but something about Darlene Love's version will always remain the standard.

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'What Christmas Means to Me,' Stevie Wonder - Let Stevie Wonder's genius grace your playlist. It is, after all, the most Wonder-ful time of the year!

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'Santa Baby,' Eartha Kitt - This playful, smoldering song was a huge hit for Eartha Kitt, certifying it a Gold Record. Only Madonna could whip up a rival cover!

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'Thank God It's Christmas,' Queen - The '80s continue to be a well of Christmas spirit for the coming years, and this hugely successful track is no exception.

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'Little Saint Nick,' The Beach Boys - Who says Christmas can't have a beachy vibe? The Beach Boys' original carol has everyone dancing around the Christmas tree.

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