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Best Christmas Songs: Crooner Classics

Updated on December 22, 2007
© Joanne Matsakis
© Joanne Matsakis

This is the second list of my personal faves. (Rockin' Christmas songs were first.) These are the traditional classics, and I've listed the versions I most prefer. There are other versions I love, of course, but hey, I can't just be making a list for every little thing, now can I? I've also included two videos of 2 songs that almost made the list, sung by 2 of my favorite singers, Andy Williams and Perry Como. I wish I could have found the others for you! All of these are available at iTunes, so go on and get your Christmas groove on!

The Most Wonderful Time of the Year

(Andy Williams)

Andy Williams has the best voice of any of the crooners. And I say that with great seriousness. You may prefer other singers over him - I personally prefer Dean Martin's music and slick style - but there is no disputing that the greatest voice of them all was owned by this man. Not to mention the sexiest. The timbre and texture and ease with which he sings was/is incredible. When I was a kid, every single house had Andy Williams on the stereo and on TV at Christmas. That's cos he was pretty much known as Mr. Christmas. I don't think anyone my age or older doesn't know this song - and I'm pretty sure the version you're most familiar with is his. It was his theme song, more or less. I couldn't find a video of it, but I did find a video of him singing Silent Night, so I've included it as a bonus.

Bonus: Andy Williams Singing Silent Night

White Christmas

(Bing Crosby)

No matter how many people cover this, it's always going to be Bing's song. And it's always going to make me think of that hotel in Vermont, with the doors opening and snow falling down and Rosemary Clooney and everyone else gather round that huge tree. No Christmas is complete without this one.

Baby It's Cold Outside

(Dean Martin)

Plenty of versions of this - nothing compares to Dino's, though. He knows how to live a song like no one else. There are actually a couple of versions of Dino singing it; you want the one with the chorus of chicks, not a solo singer. It sounds so much better that way. This is a classic, make sure you get it!

Jingle Bells

(Barbara Streisand)

If you've never heard this version - it's the best. Jingle Bells was a boring little diddy until Babs got hold of it. I remember my mother playing this all the time when I was a kid (along with every other Streisand record!) and I always loved this one the most. It's really a fun song, you'll want this on your iPod.

Evan's First Gingerbread House.

© Trey Ratcliff
© Trey Ratcliff

It Came Upon A Midnight Clear

(Frank Sinatra)

This was one my favorite carols to sing as a kid, just because I could play it and sing it at the same time. There are a few singers who really make this shine, but I like Sinatra's the best. His version is just fantastic. He's done tons of holiday recordings, and, in my opinion, this is his best. His voice is really spot-on in this song - it's almost magical. Give it a listen!

Carol of the Bells

(Johnny Mathis)

Johnny has a great voice, and my mother always had his records on when I was a little kid. This is one of my favorite songs, and his version is better than any other I can think of. The background singers really do a great job, and he blends in with them so well it's just too darned impressive.

Do You Hear What I Hear?

(Perry Como)

Ok, I know I already said something else was my favorite, but this was too. I love this song, and as a kid I really used to sing this one nonstop. Perry Como's sexy, manly voice really really makes it worth listening to, so make sure you get his version.

Bonus: Perry Como: It's Beginning to Look a Lot Like Christmas

The Christmas Song

(Mel Torme)

A lot of people don't know this song just from the title, so I'll clarify that this is the one that starts with "Chestmuts roasting on an open fire". Now you know, right? Ok. Well, the Nat King Cole version is pretty famous, but, to me, this is Mel Torme's song. Mostly cos he wrote it, and also cos I just think he sings it the best.

Have Yourself a Merry Little Christmas

(Judy Garland)

Did anyone ever sing this as well as Judy? Rosemary came pretty close, but I prefer this version. For some reason, despite the words, this song always sounds a bit melancholy. Actually, sometimes it sounds downright sad - but it always sounds fantastic, whatever the mood!

What Child Is This?

(Harry Connick, Jr.)

Yes, I know, Harry's not a classic crooner, the guy's only 40 year old or summat. He does, however, sound like one, and he's been recording for so long I figure that counts for something. There are other versions I prefer - Andy Williams, for example, but I didn't want to include him 3 times! This version is perfectly lovely so go on and put it on your iPod!


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