Webb Report: The 10 best Christmas songs of all time


When you stop and think about it, the lack of designated songs for our major holidays is puzzling. New Year’s Day has “Auld Lang Syne.” Halloween has … let’s go with “Monster Mash”? I guess you could play “Big Yellow Taxi” on Arbor Day, if you were so inclined. Christmas, though? The holiday season has an embarrassment of musical riches, of course.

There is truly a mind-boggling amount of Christmas songs, from public domain carols to modern pop classics to treasured midcentury chestnuts. Some holiday ditties are even heart-wrenchingly depressing. It can be a lot to wrap your ribbon around, as anyone who spins their radio dial to Majic 95.5 in December can attest.

In the spirit of Christmas elitism, let’s separate some joyful holiday wheat from the “Baby It’s Cold Outside” chaff. Here are the 10 best Christmas songs of all time. As always when we do these kinds of rankings, the methodology is incredibly scientific and does not simply involve one American-Statesman writer in his bathrobe scrolling through his Christmas playlist the morning of this column’s deadline.

10. “River” — Joni Mitchell

When I was child, I spake as a child. Now I am a man, and I have put my childish opinions about “River” away. I used to think this song wasn’t “Christmas-y” enough. It’s not rooted in the seasonal sounds many other modern classics are — no jingle bells and no lush French horn — though it does sample a bittersweet “Jingle Bells” at the beginning. In times like these, though, embracing the melancholy of the holidays seems more appropriate than ever. While plenty of contemporary artists put their spin on the blue Christmas, proper respect must be paid to Mitchell’s wish for a river she could skate away on. Sometimes, you can keep your songs of joy and peace to yourself. “It don’t snow here,” either.

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9. “Merry Christmas Darling” — The Carpenters

The power siblings of Christmas music present many strong contenders for inclusion on this list. Their “Sleigh Ride” is an orchestral delight, and “I’ll Be Home for Christmas” is somehow even more of a tear-jerker under the clarifying powers of an artist like Karen Carpenter. But “Merry Christmas Darling” is an original contribution to the seasonal songbook from the duo, and it’s a titan of the “sweetly sad letter to a loved one” genre.

8. “Underneath the Tree” — Kelly Clarkson

With my dying breath, I am going to make “Underneath the Tree” happen. In fact, I will win mainstream adulation for the original “American Idol” winner’s entire Christmas album, “Wrapped In Red.” It’s got everything you want: comforting holiday brass on “My Favorite Things,” country heartbreak on “Blue Christmas” and a stirring hymn like “Silent Night” (featuring Reba McEntire and Trisha Yearwood!). But the best showcase for Clarkson’s all-timer pop chops is “Underneath the Tree.” Part Brenda Lee, part Mariah Carey, all magic.

7. “Christmas (Baby Please Come Home)” — Darlene Love

Darlene Love is Christmas, and Christmas is Darlene Love. The underappreciated powerhouse, whose star has only risen since she hit the scene in the 1960s, recorded yearning rocker “Christmas (Baby Please Come Home)” for Phil Spector’s 1963 holiday compilation album. It’s a sneaky standard, the kind of song that permeates the holiday season without making too much of a fuss about itself. You’ve probably heard it in “Gremlins.” The thing that did the most to ensconce “Christmas (Baby Please Come Home)” in our carol culture was Love’s longstanding annual engagement singing the song on David Letterman’s late-night show. Go down a YouTube spiral and watch Christmases past flash before your eyes.

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6. “Christmas Time Is Here” — Vince Guaraldi Trio

Approximately 99 percent of the time, singing children are terrifying. This is that last percent. Is there anything more elegantly soothing than the hallmark jazz number from the soundtrack for “A Charlie Brown Christmas”? Besides a gold-plated jacuzzi, no.

5. “Have Yourself a Merry Little Christmas” — Judy Garland

Well-known as one of the saddest Christmas songs around, this one gets a pass on being potential grief-coma fuel because, heck, its payload is a ton of enriched hope. Oft-covered, most famously by Frank Sinatra, the definitive version remains Garland’s. She sang the song in 1944’s “Meet Me in St. Louis,” and it remains the stiffest upper lip in the holiday canon. The reality of life might not always match the comfort and joy of the Christmas spirit, but next year? Next year, all our troubles will be miles away. You’ve just gotta tell yourself that, sometimes.

4. “Jingle Bells” — Ella Fitzgerald

Pretty much shorthand for “Christmas song” at this point (see “River” above), naming a song “Jingle Bells” is like naming a jazz song “Saxophones.” You could pick almost any version of this song for a best-of list and be sitting pretty in a one-horse open sleigh. For my money, Ella Fitzgerald’s rendition is the clear-cut winner for two reasons: I had to find a way to get her on this list, and her strange end-of-song punctuation of “I’m just crazy ‘bout HORSES” is one of the greatest non-sequitirs in American pop culture.

3. “The Christmas Song (Merry Christmas To You)” — Nat King Cole

Roasted chestnuts are disgusting, but this song is anything but. Cole’s voice is what the abstract concept of warmth sounds like. It’s like the man opened his mouth and a roaring fire came out (hence, chestnuts). Find me a song that better captures the feeling of a wintry night, watched over by a blinking fir and filled with a spiced, warm beverage. Ya can’t! Don’t try it.

RELATED READ: Why you can't find your favorite holiday movies on streaming services

2. “All I Want For Christmas Is You” — Mariah Carey

Mariah Carey does not want to be called the “queen of Christmas.” Please adjust your phone contact lists accordingly. The diva roundly rejected that title in a recent Hollywood Reporter interview (“That is not my appellation,” she said), but there’s no running from the truth. According to Nielsen Music, 1994’s “All I Want for Christmas Is You” is the top-selling digital holiday song of all time, and it just can’t stay out of the Billboard Hot 100 each year. True Christmas-song-classic status is hard to come by. This is one of the most recent to breathe that rarefied air. It’s all there: soaring vocals, a singalong chorus, the timeless Christmas waltz between its upbeat sonic trappings and its romantic, pining lyrics. Sorry, Mariah. There are some thrones you just can’t abdicate.

1. “White Christmas” — Bing Crosby

LeBron. Serena. Meryl. Bing. What do they all have in common? They’re the greatest in their respective fields, and in the case of Der Bingle, that field is Christmas music. “White Christmas” is the best-selling record of all time, according to Guinness World Records. (That’s not just Christmas records — we’re talking all records.) It’s featured prominently in two Crosby movies, 1942’s “Holiday Inn” and the 1954 musical that bears its name. It won an Academy Award. Billboard says it’s the most-covered Christmas song of all time. The days have indeed been merry and bright for this song. But accolades and sales figures aside, “White Christmas” captures that most potent of holiday forces: memory. Even if everything is rosy, we still all long for some other Christmas, just like the one we used to know.



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