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Who Sang It Best? "Winter Wonderland"

Music enthusiast FlourishAnyway introduces some fun competition into the holidays by ranking cover versions of popular Christmas songs.

Some of the best-known Christmas songs have been covered by a variety of artists. We look at the classic tune "Winter Wonderland"—the happy song with the sad past—and rank 14 contenders. Who do you prefer?

Some of the best-known Christmas songs have been covered by a variety of artists. We look at the classic tune "Winter Wonderland"—the happy song with the sad past—and rank 14 contenders. Who do you prefer?

The Sad Origins of "Winter Wonderland"

Young Richard B. Smith suffered from several bouts of tuberculosis in the early 1930s. Tuberculosis, also called "consumption," was a devastating and highly contagious disease that caused symptoms of weakness, fever, a blood-stained cough, and wasting away.

As the Honesdale, Pennsylvania, man sat holed up in his West Mountain Sanitarium room, he watched children playing gleefully in the snow below. Smith started to daydream about life beyond the walls of the hospital where he was confined. His musings inspired him to write a poem that was eventually set to music.

Smith died from his tuberculosis in 1935, just a day before his thirty-fourth birthday. However, the young man left behind a musical legacy that he was little aware of—this holiday classic, "Winter Wonderland." Many artists have since released the song, and musical styles and levels of quality have varied considerably. Thus, do you ever wonder, "Who sang it best?" Here's your chance to step up and compare their efforts.

"Who Sang It Best?": Here's How It Works

With many artists singing the same Christmas tunes, the sleigh has become overloaded. Let's rank them and cross some versions off the list.

In the "Who Sang It Best?" series, we start with the original rendition of popular songs that have been covered multiple times. Then we present a set of contenders, artists who have released cover versions in any genre. Some cover versions honor the original artist's style while others are reinterpretations.

Since the original song version is typically considered "the standard," we don't include it in our overall rankings. Instead, we display it first for comparison, with up to 14 contenders presented next in ranked order. Vote on your preferences:

  • Do you prefer the original song or a cover version?
  • Of all the cover versions, which you prefer?

"Winter Wonderland" by Johnny Mercer & The Pied Pipers (1946)

"Winter Wonderland" is another holiday favorite that ironically doesn't mention Christmas, but it's festive just the same. (Or at least it was intended to be.) The song depicts a couple taking a gleeful stroll in the snow together. The man sings a love song to his partner. They frolic in the snow together and build a snowman. Then they pretend that the snowman is a nondenominational preacher who will pronounce them husband and wife. Later, the couple relaxes by a fire and discuss their shared future.

More than 200 different artists—including Elvis, Perry Como, and Radiohead—have covered "Winter Wonderland" since it was first released in 1934 by bandleader Richard Himber. We're using the 1946 rendition by Johnny Mercer & The Pied Pipers to represent the classic version of the song. It climbed to #4 on the Billboard charts.

Johnny Mercer was a popular singer-songwriter, Broadway composer, and co-founder of Capitol Records. The Pied Pipers performed both on their own and in association with artists like Frank Sinatra. The group is still active today.

Together Mercer and his gaggle of backup singers deliver the most depressing version of "Winter Wonderland" I've ever encountered. Their blunted emotion makes me question the happiness of the couple, the setting, and the winter wonderland altogether. Should they be breaking up instead?

Their execution of this classic is unusual in that nearly any cover version can beat it. The song drags unnecessarily, as if Johnny Mercer & The Pied Pipers were channeling the bleakness of a dying Richard B. Smith, the writer of the song who was confined in a tuberculosis ward for four years. I attribute the joyless singing more to The Pied Pipers than to Johnny Mercer, however. He proved how effectively he could let his personality shine through in songs like Baby It's Cold Outside.

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This Christmas classic will be easy to beat with any cover version you choose. Just pick one.

1. "Winter Wonderland" by Dean Martin (1957)

Cozy up the fire with your loved one as you listen to this flirty version. Confident Rat Packer Dean Martin delivers in his rendition of this enduring classic.

Known for his suave manner, the actor, singer, and comedian was awarded three stars on Hollywood's Walk of Fame. Martin was regarded as "The King of Cool" because of his charm. He was awarded a posthumous Grammy Lifetime Achievement Award (2007).

2. "Winter Wonderland" by Lauren Daigle (2016)

Some critics describe contemporary Christian artist Lauren Daigle as the next Adele or Amy Winehouse. I doubted that was within reason until I heard Daigle in this jazz rendition of "Winter Wonderland." It's classy and laid back with a sophisticated retro vibe. Watch Daigle's Christmas songs to become a new generation of classics. You go, girl.

3. "Winter Wonderland/Don't Worry Be Happy" by Pentatonix (Featuring Tori Kelly) (2014)

Wait, what's going on here? Is this a musical mashup of two songs?

Yes, "Don't Worry, Be Happy" by Bobby McFarlane (1988) has melted into "Winter Wonderland," and the merger magically works, although I didn't imagine it would. (I thought there would be just too much going on lyrically.)

However, the combination song employs a simple beat, instrumental minimalism and the magical, diverse voices that make Pentatonix so popular. Well known for their a capella renditions of pop favorites, the group has won both Grammy and YouTube Awards and has garnered more than 3.6 billion YouTube views.

4. "Winter Wonderland" by Darlene Love (1974)

In an energetic, enthusiastic rendition of "Winter Wonderland" reflective of the 1960s girl groups, Darlene Love delivers this hand-clapping favorite. (Yes, there is hand-clapping in there, but don't knock what works.)

It's no wonder that Rolling Stone named Love to their list of "100 Greatest Singers of All Time." Listen for the altered lyrics (now a standard option) and "wo-oh-ohs" that make that make her a distinctive force in music:

In the meadow, we can build a snowman
And pretend that he's a circus clown
We'll have lots of fun with Mr. Snowman
Until the other kiddies knock him down

When it snows, ain't it thrillin'
Though you know, kids are chillin'
We'll frolic and play, the Eskimo way

Walking in a Winter Wonderland (wo oh oh . . . )

5. "Winter Wonderland" by Leona Lewis (2013)

Low-key, this cover is decidedly NOT! I love this upbeat, Motown-inspired rendition of "Winter Wonderland" with Leona Lewis' soaring vocals. Lewis is a classically trained British singer-songwriter who was catapulted to fame when she won the third season of The X Factor.

Rather than tiptoeing around this song, Lewis gives it a big ole bear hug and sings it loud and proud. If you're feeling rundown from all the holiday shopping, grab some of your favorite Christmas cookies and put this song cover on "loop" until you feel better. It shouldn't take long!

6. Winter Wonderland" by Amy Grant (1992)

In this light, airy cover of "Winter Wonderland," Amy Grant's voice is the focal point. Rather than hide behind overpowering instrumentals, she showcases her talent by adding her own creative intonations to the lyrics, thus making the song truly hers.

Grant became famous as "The Queen of Christian Pop" then achieved mainstream crossover success, earning a star on the Hollywood Walk of Fame. She attended Vanderbilt University, the same university I graduated from, and for many years she has held annual events for Christian students at Vandy, as well as community fundraiser benefits at her farm outside Nashville. The Grammy and Dove Award-winning star is married to prominent country music singer Vince Gill.

7. "Winter Wonderland" by Michael Bublé (2011)

If you like the peppiness of the big band sound, then this cover version delivers strong. Michael Bublé offers charismatic vocals in the style of yesteryear's crooners. Three-quarters of the way through this song he really gets down, adding his own personality and creativity in executing the lyrics.

The Canadian singer is a multiple Grammy winner known for his Sinatraesque style. If you're a Bublé devotee, also check out his duet with Rod Stewart from his 2012 "NBC Home for Holidays" special, as Bublé demonstrates how he can musically hold his own singing with the living rock legend.

As a youngster, Bublé used to pray to become a professional hockey player for the Vancouver Canucks. There's a lesson in there about unanswered prayers!

8. "Winter Wonderland" by Johnny Mathis (1958)

Johnny Mathis' voice floats and flutters in this beautiful rendition of "Winter Wonderland" while the background instrumentals provide a dreamy, nostalgic air. The Grammy Hall of Fame artist is particularly noted as a voice of romance. This cover is far superior to Mathis' 2006 collaboration with Bette Midler.

9. "Winter Wonderland" by Sugarland (2009)

This cover is twangier than most with its jammin' guitars and Jennifer Nettles' raspy Southern drawl. If you enjoy country music as I do, then you'll want to grab a partner and boot scoot to this particularly cheerful rendition of "Winter Wonderland." You'll be happily "rocking all the way to Sugarland." Sugarland is a Grammy Award-winning duo known for its series of mainstream crossover successes.

10. "Winter Wonderland" by Gwen Stefani (2017)

Gwen Stefani isn't typically vocally restrained, but in this cover of "Winter Wonderland" she holds back her voice and doesn't fully belt it out. Why do that? As she zoop-zoops her way through this holiday favorite, Stefani allows the dramatic music to take precedence over her vocals, and that's a real shame.

While this cover version is not bad, it is also unremarkable. If it had been released by a less prominent artist, then it would have easily disappeared from radio play before Santa loaded his sleigh.

11. "Winter Wonderland" by Brad Paisley (2006)

Full of playfulness, this cover is a fun country rendering of the Christmas classic, "Winter Wonderland." Brad Paisley alters the lyrics somewhat to give a nod to a Country Music Hall of Famer, Jim Ed Brown, famous for the song, "Pop a Top" (which Alan Jackson rerecorded in 1999.)

Here's how Paisley altered "Winter Wonderland's" lyrics to honor the late Hall of Famer:

In the meadow, we can build a snowman
And pretend that he is Jim Ed Brown
We'll sing "Pop a Top" with Mr. Snowman
When chapel bells are ringing all around.

Brad Paisley is a Grammy Award-winning country singer-songwriter known for his musical versatility—from humorous songs like "Ticks" (2007) to those that are tragic and sentimental like "Whiskey Lullaby (2004)". He is the long-standing co-host of the annual Country Music Association Awards, along with Carrie Underwood.

12. "Winter Wonderland" by Selena Gomez and The Scene (2009)

Selena Gomez has come a long was since the one-time Disney princess left The Scene behind. They were a recurring teen favorite back in their day, and this cover song accordingly reflects it.

The cover has a very teen vibe, hard-driving background instrumentals, and several inexplicable exhortations of "Oww!" Even though Gomez is singing "Walking in a winter wonderland," I swear I think I hear, "Rocking in a winter wonderland." Maybe it's my old ears?

13. "Winter Wonderland" by Eurythmics (1987)

If you're not aware that the Eurythmics' cover has a different intro, you might think you have the wrong song playing. The first two stanzas don't seem to be a stylistic match for the rest of the song, albeit the theme is consistent:

Over the ground lies a mantle of white
A heaven of diamonds shines out through the night
Two hearts a-thrilling
In spite of the chilling weather

Love knows no season, love knows no clime
Romance can blossom any old time
Here in the open
We're walking and hopin' together ... .

I'm not fond of this reimagination of the original song. Nor am I enamored with the prominent electronic background instrumentals in this 80s cover of "Winter Wonderland." They threaten to overpower Annie Lenox's vocals, and that's hard to do. (Dial it down and let us hear her sing.) Eurythmics was a Grammy Award-winning duo that sold an estimated 75 million records globally during their career.

14. "Winter Wonderland" by Jason Mraz

Singer-songwriter Jason Mraz wandered way off the musical script with this cover. Granted, the "I'm Yours" singer to do something different. But it didn't work, at least not in my book. Mraz oversings his lyrics in key parts, offers up meandering "bop-de-bop" improvisational lyrics (yuck), and allows a background singer to echo him. His copycat echo singer comes across like a lady heckler, and the effect is distracting. Do yourself a favor and skip this rendition.

Mraz is a Grammy Award winner and was inducted into the Songwriters Hall of Fame (2009).

© 2018 FlourishAnyway


FlourishAnyway (author) from USA on March 28, 2020:

Peggy - Glad you learned something and enjoyed several of the artists.

Peggy Woods from Houston, Texas on March 28, 2020:

I never knew the origin of this song. How sad that Richard B. Smith died at such an early age of TB. As to who sang it best, there are so many singers with excellent voices that it is hard to pick just one.

FlourishAnyway (author) from USA on December 02, 2019:

Louis - Thanks for your input. Merry Christmas!

Louis Tan on December 02, 2019:

Who sang it best? None of the above! Connie Francis did! Simple and classy

FlourishAnyway (author) from USA on November 28, 2019:

George - I'm glad you found this article enjoyable. Thank you for taking the time to leave a comment.

George Xu from Philippines on November 27, 2019:

I do love jazz so Lauren Daigle's version would catch my ears, but it's not the best. I would say I love Amy Grant the best.

FlourishAnyway (author) from USA on January 25, 2019:

John - Thank you so much for your off-season visit! It's nice to have visitors even after Christmastime.

John Hansen from Gondwana Land on January 24, 2019:

This was such a hard decision, Flourish. I really loved the two country versions By Sugarland and Brad Paisley. I love Michael Buble's also but I do feel he modelled his vocals quite a bit on Dean Martin's version. Pentatonix and Amy Grant's were very good too, but I chose Lauren Daigle's as my favourite. I love these "Who Sang It Best?" hubs.

FlourishAnyway (author) from USA on January 01, 2019:

Jo - Both my sister and I graduated from Vandy, and I tried to get my daughter to apply, too, but she would have none of it. I loved it there! I have friends who loved Nashville so much they stayed there after college. Wishing you all the best for 2019!

Jo Miller from Tennessee on December 30, 2018:

What fun!!! Enjoyed listening to these now that the season is about over here . Really enjoyed Lauren Daigle, Amy Grant, and Michael Buble. I picked Buble as the one who sang it best, but my personal favorite would probably be Amy Grant, probably because of her connection to Vandy. We have our personal connections to that university here in Tennessee.

FlourishAnyway (author) from USA on December 29, 2018:

Nathan - Thank you for stopping by to comment and register your opinion. Have a wonderful 2019!

Nathan on December 28, 2018:

It has to be the Mathis version, for he seems to capture the spirit and mood of the song and sings it so well in the fun element and spirit of Christmas, faultless vocalist..

FlourishAnyway (author) from USA on December 28, 2018:

Shauna - You're a real trooper for testing them all out start to finish before deciding. I sure hope you had a wonderful Christmas and hope that 2019 will be good to you.

Shauna L Bowling from Central Florida on December 28, 2018:

Well, I finally got thru all the videos, Flourish. I really like Darlene Love's rendition, but I'm a sucker for Johnny Mathis. I have to go with him as my fav in this lineup.

FlourishAnyway (author) from USA on December 26, 2018:

Heidi - Thanks for stopping by. I hope you had a joyful holiday.

Heidi Thorne from Chicago Area on December 26, 2018:

I like Bing Crosby's rendition, too. Hope you had a very Merry Christmas. Happy New Year!

FlourishAnyway (author) from USA on December 26, 2018:

Devika - That's a surprise! At least somebody likes the original. Hope your Christmas was a merry one.Thanks for commenting.

Devika Primic on December 26, 2018:

Many versions and I had no idea of it. I know the original is the best for me.

FlourishAnyway (author) from USA on December 26, 2018:

Shaloo - Thank you for stopping by. I hope you have a wonderful week.

Shaloo Walia from India on December 26, 2018:

I wasn't aware that so many versions exist...thanks for sharing!

FlourishAnyway (author) from USA on December 25, 2018:

Linda - Have a wonderful Christmas holiday! I wish you all the very best. I can smell your cooking from here.

FlourishAnyway (author) from USA on December 25, 2018:

Linda - I appreciate your stopping by. Have a very Merry Christmas!

FlourishAnyway (author) from USA on December 24, 2018:

Tim - You are always so kind and encouraging. I appreciate your support. May the best of the holidays be yours this season. Have a Christmas Eve filled with joy!

FlourishAnyway (author) from USA on December 24, 2018:

Genna - Thank you again for visiting my "Who Sang It Better?" articles. I've enjoyed putting them together and hope you liked comparing the versions. Have a wonderful Christmas Eve waiting up for Santa!

FlourishAnyway (author) from USA on December 24, 2018:

Clive - Have a delightful Christmas. You should let us know how Christmas is done in Jamaica.

Genna East from Massachusetts, USA on December 24, 2018:

Michael Buble gets my vote here. But there are other great renditions of this timeless classic you've given us. This is the second musical hub I've enjoyed this morning. Such a lovely way to greet Christmas Eve, my friend, Thank you, and best wishes for a happy Christmas.

Clive Williams from Jamaica on December 24, 2018:

I love these songs. oh my heart!

Linda Crampton from British Columbia, Canada on December 23, 2018:

I didn't realize that this song had such a sad background. I didn't know that several artists had changed the lyrics, either. Thanks for sharing the information, Flourish.

Linda Lum from Washington State, USA on December 23, 2018:

Flourish, I guess the only version I DON'T like is the original. It's more of a dirge. Good grief!

It's hard to not like Dean Martin's version and I guess he gets my top vote although the Pentatonix version I had not heard of--I didn't see how it could work, but it did. They're in 2nd place.

Buble didn't get my vote; although I really like his voice (yes he is a bit like Sinatra) but the "big band sound" just doesn't seem right with this one.

Thanks for another great hub. I hope you've had as much fun putting these together as we have enjoyed listening to them. Merry Christmas my dear and we'll "talk" next Monday over cookies and the mailbox.

Tim Truzy from U.S.A. on December 23, 2018:

Hi, Flourish,

Your usual superb job on your research. I'm a fan of Mathis, but Martin is cool in his rendition. The country versions are OK, but I would put Pentatonix third because they did something no one else could have done with the tune. Amy Grant is fabulous. I've always liked her. She earns fourth place for my taste. Hey, by the way, with Glen Fry passing from the Eagles, V. Gill is now an Eagle. That earns Amy and Gill some extra cool points from me.

This is one of my favorite holiday tunes. Thanks, I didn't know there were so many versions of the song, and the story behind it is extremely sad.

May your holidays be peaceful and joyous.

To a talented, kind and thoughtful writer,

Much respect from me.


FlourishAnyway (author) from USA on December 23, 2018:

Doris - I love anything with a Motown flavor, too. Thank you for your thoughtful commentary. I wish you and your family all the best this holiday. Merry Christmas!

Shannon Henry from Texas on December 23, 2018:

Oh no, you couldn't ruin that song for me. Except maybe listening to that sad, slow version.

FlourishAnyway (author) from USA on December 23, 2018:

Liz - I'm always going to think about that when I hear the song. Hope you have a Merry Christmas!

FlourishAnyway (author) from USA on December 23, 2018:

Shannon - After I told my daughter about the sad song background, she said I ruined the song for her. I hope I didn't do that for you, too. There are so many good editions. I switched out Dean Martin in the first position. Thanks for stopping by.

FlourishAnyway (author) from USA on December 23, 2018:

Ann - Merry Christmas! Thanks for stopping by! Glad you enjoyed this!

FlourishAnyway (author) from USA on December 23, 2018:

Bill - Jennifer Nettles could sing the ingredients off the back of a shampoo bottle and I'd think it was gorgeous. She's amazing. Merry Christmas to you too!

FlourishAnyway (author) from USA on December 23, 2018:

Pamela - There are a lot of good ones here! Being far down on the list doesn't mean they're bad versions. Thanks for stopping by! Merry Christmas to you too!

Doris James MizBejabbers from Beautiful South on December 23, 2018:

Flourish, I made some notes as I listened to these different versions, just in case my comment sounds like I'm rambling. I'd never heard the version by Pentatonix, but it's funky and I kind of like it.

My favorite though has to be Darlene Love, but hey, it's a Phil Spector production. What can I say, I've always had a soft spot in my heart for anything Phil Spector. I also like the 2009 Motown copy sound of Leona Lewis. Both of these sounds originate back in the days when I was just breaking into radio, so I'm kind of prejudiced.

I find both country versions very listenable, but I guess I favor Brad Paisley. So that concludes my three favorites.

I agree with your assessment of the dead sounds of Johnny Mercer with one addition. It's a bad mix. Of course, back in 1946, the equipment of Capital Studios, or any other sound studio, was still primitive compared to those of today . However, you've probably noted that a lot of old re-releases will say "a remix". This one could use a modern remix and digitizing.

You did your usual great job, Flourish. I enjoyed this one very much.

Liz Westwood from UK on December 23, 2018:

What a sad story behind the writing of this song. I would guess that, like me, most people who hear it are unaware of its sad origins.

Ann Carr from SW England on December 23, 2018:

No contest! Dean Martin's voice gets me every time, so it has to be him and Frank Sinatra who was my Mum's favourite.

I like this series; it's fun. Thanks, Flourish!


Bill Holland from Olympia, WA on December 23, 2018:

I'll give this one to Sugarland just because I love her voice. :) Merry Christmas to you and your family, my friend!

Pamela Oglesby from Sunny Florida on December 23, 2018:

There are just too many good ones to actually choose only one. It is a beautiful holiday song. I like Dean Martin and Frank Sinatra, but I also like many of the newer ones. Quite a job to post this much information along with all these versions! Merry Christmas.

Shannon Henry from Texas on December 22, 2018:

This is in of my all time favorite Christmas songs. I never knew the history behind this particular Christmas song. Thanks for sharing it. Like "Mary Did You Know", it's usually hard for me to find a version of this song I don't like. But you found one with the classic version you used. Maybe he was channeling the melancholy of the inspiration behind the song. Even so, I like it much better as the cheerful song most of us know it as.

I was surprised by the Pentatonix version. Just because I never would have imagined those two songs to mash well together. Of course, that group seems to nail everything they do, especially Christmas songs.

As a side note, I couldn't find "Winter Wonderland" in that hour long Sinatra and Martin video. No time to listen to the entire album.

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