12/11/2013 01:07 EST | Updated 02/10/2014 05:59 EST

The Best (and Worst!) Christmas Music

It's beginning to look a lot like Christmas, and with just under two weeks until the Jolly Old Elf arrives, it's really beginning to sound like it, too.

It's at this point in the year that I really begin to enjoy Christmas music (for the most part, anyway), and love hearing the strains of "O Holy Night" or Bono belting out "well, tonight thank God it's them, instead of you" from my iPod or the all-Christmas station several times a day.

As it is every Christmas season, there are a few songs I've already heard one time too many, some that seem to be on the low-rotation list, and a couple I will never hear unless I download them myself.

For all its festive fa-la-la-la-la, Christmas music can be divisive. Either you love the Glee cast singing covers of Christmas songs, or (like me) you don't. Touching Christmas songs are fine. Songs about mothers dying on Christmas Eve are just plain wrong. So are unnecessary remakes of songs (Whitney Houston's "Do You Hear What I Hear?" is lovely. Band Aid remakes and covers are not.). Sorry, Sirs Elton and Paul: Your Christmas songs aren't going to make your Greatest Hits compilations. I've seen countless blog posts and heard pundits wading into the fray with the best and worst Christmas songs of all time.

So in that spirit, here's the go-to playlist for a Pellegrini Christmas:

The Classics

I'd have a hard time saying anything bad about the traditional Christmas carols. "Joy to the World", "Away in a Manger", "Silent Night", "O Come All Ye Faithful" -- anything in that category gets cranked up loud when it comes on the radio. Depending (of course) upon who sings it.

Then there are the "old" Christmas songs; you know, the ones your parents and grandparents hum while they wrap presents and bake shortbread. After all, who can resist Ol' Blue Eyes crooning "Santa Claus is Coming to Town"?

The big stars of the 40s and 50s really own those classic songs -- Burl Ives wishing listeners a "Holly Jolly Christmas", Gene Autry singing "Here Comes Santa Claus" and "Rudolph the Red-Nosed Reindeer", Jimmy Durante's unique version of "Frosty the Snowman", and Nat King Cole's "The Christmas Song" really are the gold standard for traditional Christmas tunes, joined by Dean Martin's "Winter Wonderland" and Elvis's "Blue Christmas".

But it's Bing Crosby who set the bar for Christmas classics. Whose heart doesn't melt just a little bit when "I'll Be Home for Christmas" comes on the radio? It's a wartime song, and we all know he isn't going to make it back.

Bing kind of cornered the market on Christmas tunes; along with "I'll Be Home For Christmas", he also sang "White Christmas", a gentle little version of "Do You Hear What I Hear?", and "Mele Kalikimaka", along with The Andrews Sisters.

Then, after years of being kind of relegated to the Old Boys Club, Bing re-invented himself in 1977. He paired up with a strange-looking English fella, and recorded an all-new version of "The Little Drummer Boy". While he pa-rum-pa-pum-pumed, David Bowie sang about hoping for peace on Earth. Strange fact: Bowie was a youthful 30 when that song was recorded on September 11, 1977, two years older than the song itself. Bing Crosby was 74 and died just a month later, on October 14. And today, Bowie's only eight years younger than Bing was back in 1977.

Modern Classics

Oh, it's a long, loooong list of songs. At the top, it has to be "Fairytale of New York", by The Pogues. Whether it's the unlikely musical pairing of Shane MacGowan with the late Kirsty McColl, the achingly beautiful lyrics of love and loss, optimism and despair, or the swelling sound of the string arrangement at the end, it's the one song I could listen to all day and still be as moved the last time I hear it as the first.

Next up: Band Aid's "Do They Know it's Christmas?". Well, of course they didn't. After all, this was 1984. But it's the song that launched a dozen other relief efforts. I turned 17 that December, and "Do They Know it's Christmas?" was the awakening of my social conscience. Whenever I hear that song, I can see the video in my mind's eye. So I guess it's a bit like my generation's "White Christmas".

Other modern Christmas classics that make our Christmas complete include (in no particular order): Bruce Springsteen and the E Street Band's "Santa Claus is Coming to Town" (although I confess to feeling a bit sad now that The Big Man is playing the saxophone with the angels) and "Merry Christmas Baby", Wham's "Last Christmas", "Baby, Please Come Home" (U2), "(It Must Have Been Ol') Santa Claus" (Harry Connick, Jr.), "Winter Wonderland" (The Brian Setzer Orchestra), "Happy Christmas (War is Over)"by John Lennon and Yoko Ono, "All I Want for Christmas (Is You)" -- but only by Mariah Carey, "Santa Baby" (Eartha Kitt is best, but Madonna's version will do in a pinch), "I Saw Mommy Kissing Santa Claus" (John Mellencamp), "Run Rudolph Run" (Chuck Berry), "Little Saint Nick" (The Beach Boys), Hall and Oates' "Jingle Bell Rock", "Same Auld Lang Syne" (Dan Fogelberg), "River" (Sarah McLaughlin), "Christmas Wrapping" (The Waitresses), anything by Straight No Chaser, and the various versions of "The 12 Days of Christmas", including versions by The Muppets, Straight no Chaser, and Bob and Doug McKenzie.

Honourable mentions to the kitschy Christmas classics:"Dominick the Donkey", "Hippopotamus for Christmas", "Hey Santa Claus" and (although it used to upset my daughter every year when she'd hear it), "Grandma Got Run Over by a Reindeer".

And finally: Anything from a pre-1976 Christmas special, especially A Charlie Brown Christmas, How the Grinch Stole Christmas, and Year Without a Santa Claus. A special mention: "Honky the Christmas Goose", by Johnnie Bower and the Rinky Dinks. It's a McKenzie family tradition, and Christmas just isn't Christmas without it.

What tops your list? What song leaves you diving to switch the station? Do you have a hidden gem? If you do, be sure to share.