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Chris Colfer and Darren Criss, ''Baby It's Cold Outside''
The traditionally male/female duet got a much-needed shakeup when Glee had the adorable Blaine and Kurt perform it during season 2's ''A Very Glee Christmas.'' The most shocking thing about this duet isn't its two male singers; it's just how simple and classic the typically over-the-top show kept this version.
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Nat King Cole, ''The Christmas Song''
This first recorded version of the song was inducted into the Grammy Hall of Fame in 1974. Just like the casual video of a cross-armed Cole simply singing the song, the big-band baritone makes the Christmas classic seem effortless.
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Judy Garland, ''Have Yourself a Merry Little Christmas''
Our little Dorothy is all grown up in 1944's Meet Me in St. Louis, but her trademark vibrato is exactly the same. How could Garland's movie sister not be comforted by that soothing voice?
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Harry Connick Jr., ''Let It Snow!''
The new American Idol judge's vocals are so delightful, but this arrangement is all about that horn blast after his first line — pleasantly catches us off-guard every time! And the brass comes back in a big way for the bombastic finale, with Connick?s tenor harmony perfectly riding the trumpet line.
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Bing Crosby and David Bowie, ''The Little Drummer Boy''
This version is EVERYTHING. Back in 1977, the straitlaced Bing and subversive Bowie teamed up for a lovely take on the Christmas classic, interspersed with an original tune, ''Peace on Earth.'' Bowie has said he agreed to the TV special, titled Bing Crosby's Merrie Olde Christmas, because his mum loved Crosby. The White Christmas actor/singer died five weeks after filming, leaving behind this wonderful gift.
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Josh Groban, ''O Holy Night''
Josh Groban's classical style is perfect for this song, and he takes a unique lyrical spin on it, performing the little-heard verse that begins ''Chains shall he break for the slave is our brother.''
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Burl Ives, ''Rudolph the Red-Nosed Reindeer''
This is the version from the stop-motion animation TV special inspired by the song. As a child, you might have thought a jaunty snowman with a banjo sang this, but it was really Burl Ives the whole time.
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Bruce Springsteen and the E Street Band, ''Santa Claus Is Coming to Town''
This live version was recorded at a 1975 concert on Long Island and wasn't officially released until it showed up as a B-side on the 1985 single ''My Hometown.'' Somehow, Bruce takes a song about Santa and makes it into a rock and roll classic.
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Kelly Clarkson feat. Reba McEntire and Trisha Yearwood, ''Silent Night''
Three times the country divas! The best part about their performance is that each lady gets her time to shine and then happily takes the backseat before all coming together for a glorious three-part harmony.
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The Ronettes, ''Sleigh Ride''
This Wall of Sound is A Christmas Gift for You From Phil Spector. (Might be wise not to accept any more gifts from that dude, but the Ronettes can come over for Christmas anytime.) The ring-a-lings throughout make this version extra festive.
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Bing Crosby, ''White Christmas''
Crosby originated the song in the 1942 movie Holiday Inn, and continued to sing it until his death in the '70s. Bing also made the movie White Christmas in 1954, in which he reprised his wildly popular holiday hit. Oh, and did we mention that his version is the best-selling single of all time?
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Darlene Love, ''Winter Wonderland''
Whether you remember it from Phil Spector's 1974 holiday album, '80s movies like Fast Times at Ridgemont High or Better Off Dead..., or from 2006's The Holiday, you know this classic version of the song.
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Bonus Track! Mariah Carey, ''Al I Want for Christmas Is You''
Because you can't have a comprehensive holiday playlist without Mariah. It's the law.