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Holiday Classics-Who sings it best?

Updated on February 28, 2014
Picture source: Wikimedia Commons (Garland, public domain) (Bublé, Jeanie Mackinder , CC BY 2.0)
Picture source: Wikimedia Commons (Garland, public domain) (Bublé, Jeanie Mackinder , CC BY 2.0)

December first, every year I load up my IPod shuffle with a full holiday playlist, nothing else, and I'm proud to say it is eclectic. One of the great things about Holiday music is the mix of old and new; traditional and not-so-much. There are the classics as a starting off point and then there are so many different versions of them. I enjoy hearing the different takes on them by contemporary artists. I also love when the classics are shaken up a bit and made to sound more modern as well. Let’s take a look at some head to head competition to see who prevails and please let me know what you think in the comments section!

Baby it’s Cold Outside

Dean Martin & Marilyn Maxwell* vs. Zooey Deschanel & Will Ferrell in the movie Elf

I have to go with Dean Martin & Marilyn Maxwell on this one- the major thing I love about this song is it brings us back to that particular time period where unmarried couples or love interests had to be discreet about their budding romance. The female lead keeps insisting she has to leave otherwise everyone will gossip. This is a tough category for me to choose a clear winner because I really enjoy hearing new duets of this song. I love the version that takes place in the movie Elf between Zooey Deschanel and Will Ferrell. (The soundtrack version features Leon Redbone instead of Will and I understand Ferrell is not a trained musician but I enjoy the movie version better).

*It is hard to track down exactly who is singing with Dean Martin on his classic version, which is a shame. It seems Marilyn Maxwell is in the version I am familiar with based on a YouTube search. (There is another version that features a chorus of unnamed women but it's a duet so it doesn't really make sense to have a chorus singing the female vocal, in my opinion)

Bonus option- I actually really love two, additional contemporary versions of this song- one was sung by Chris Colfer and Darren Criss as Kurt and Blaine on Glee. I think having a gay couple sing this song adds another layer to it. In this updated version they have to be discreet due to homophobia, it makes the lyrics of the song represent something totally different. I also love the American Idol version that features Haley Reinhart and Casey Abrams.

American Idol's Casey & Haley's version of 'Baby It's Cold Outside'

Santa Baby

Eartha Kitt vs. Madonna

I have to go with the more contemporary version on this one. Overall the Eartha Kitt one is too slow for me and although at times the baby voice Madonna uses becomes annoying for the most part it works. It also seems current remakes of this song mirror the Madonna version so unfortunately for Eartha it seems Madonna has the trophy on this one.

Other options- Kylie Minogue, the Pussycat Dolls.

Have Yourself a Merry Little Christmas

Judy Garland vs. Michael Bublé –This is a tough one to call since I respect Michael Bublé’s contribution to the Christmas Canon. It doesn’t hurt that he has that throw-back vibe. But I have to go with the original, Judy Garland's version on this one. The song is a bit melancholy (interestingly the lyrics were originally written to be even more dreary and Garland and her costars insisted the lyricist make a few changes for the song in Meet Me in St.Louis) and I feel Garland’s voice best captures that tone.

Bonus option- I love the John Denver and Rowlf (from the Muppets) version of this song as well.

Judy Garland in Meet me in St.Louis

In general who do you prefer sing these Holiday songs?

See results

The 12 Days of Christmas

John Denver and the Muppets vs. Straight No Chaser

I’ll admit neither of these two selections are really the classic version but they are my favorites. I absolutely love Straight No Chaser’s Christmas stuff so I had to get a plug in for them. I enjoy pretty much every twist on a classic that they have, I’m not really religious and I even enjoy their religious carols. Also they have a few original songs that are great and coming out with successful new Christmas songs is no easy feat. But I have to give a slight edge to the Muppets as far as the 12 days of Christmas is concerned, because they are the Muppets. It's a really close call though, I absolutely love how Straight No Chaser works in Toto's Africa to their rendition, it is genius.

John Denver & The Muppets

It’s the Most Wonderful Time of the Year

Andy Williams vs. Johnny Mathis

Sorry but this is Andy Williams' song- no competition in my book.

Other options- Scott Weiland, Harry Connick Jr.

Andrew Williams singing It's the Most Wonderful Time of the Year

Great Contemporary Original Christmas Songs

1. All I Want for Christmas is You- Mariah Carey

2. Last Christmas- Wham!

3. Christmas Wrapping- The Waitresses

4. The Christmas Song-Weezer

5. Who Spiked the Eggnog?- Straight No Chaser

White Christmas

Bing Crosby vs. Frank Sinatra

I’m not even going to bother throwing a more contemporary version in with these two older versions. They are pretty similar sounding but I’m going to have to go with Frank Sinatra’s version. I will say that no one else can do ‘Hawaiian Christmas,’ Crosby has the sole right to it.

Other options- Lady Gaga, Kelly Clarkson.

Merry Xmas (War is Over)

John Lennon & Yoko Ono vs. Celine Dion

This is the song I am most firm on. No remakes, only John Lennon & Yoko Ono can sing this.

Other option- Sarah McLachlan.

Please Come Home for Christmas

Charles Brown vs. The Eagles

To be completely honest I didn’t know about the original until I wrote this hub, I suspected the Eagles didn’t write the song but I was not familiar with the original. So I am definitely biased in announcing the winner as the Eagles since I’ve now only heard the original a few times. But I have always loved Don Henley’s voice so I suspect hearing Charles Brown’s version more times still wouldn’t sway me.

Other options- Fiona Apple, Martina McBride, and Kelly Clarkson.

The original version of Please Come Home for Christmas

All I Want for Christmas is You

Mariah Carey vs. My Chemical Romance

This song is the example of a successful new Christmas song and it has become one of the most popular overall, so hats off to Mariah Carey on this. There are a lot of good remakes of this song but no one can top Carey if they are doing a straight up knockoff of the powerhouse female vocal rendition. So really for me the only contender for an alternative is in fact a rather alternative version of the song done by My Chemical Romance.

I could go on and on, there are many artists and songs I didn't even get to that I consider essentials. Keep an eye out next year for a part two in December. Until then Happy Holidays!


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