Christmas Playlist for the Win!

Christmas Playlist for the Win!

As I mentioned in my last post, I have no problem cranking up a Christmas song in the middle of summer if my mood calls for it. Christmas music is kind of like laughter—it’s impossible to participate in it & be negative. So when Thanksgiving took its final bow, there was no more limiting how often we could rock around the Christmas tree (which is up but barely decorated due to a certain short person).

I went through my Christmas albums and composited a playlist of my top favorite songs. I hope there’s a new song or two for you to add to your collection!

  1. Baby, It’s Cold Outside, Louis ArmstrongLA

This is one of my favorite versions of this fun & flirty song. I feel like I’m sitting in Louis’ audience in my fur coat, red lipstick, sipping a gin martini.


  1. White Christmas (1942 Holiday Inn Version), Bing Crosbyholiday inn

The fact that a classic Christmas movie was based off this song shows how imperative it is to this season. Bing Crosby is a Christmas miracle.



  1. O Holy Night, Folk Angelfolk angel

Folk Angel took my favorite Christmas song, added a verse, & made it an incredible worship experience. This song is gold.


  1. Rockin’ Around the Christmas Tree, She & Himshe & him

Zooey Deschanel’s voice makes me happy, & this is such a perfect song for decorating the tree or hosting a gingerbread house-decorating contest.


  1. O Come All Ye Faithful, Josh Grobanjosh groban

This song was my favorite in high school because I loved the way it sounded on the violin, & Josh Groban takes his version to a whole new level by pairing with the Mormon Tabernacle Choir. I’m not even big on organ music, but that last verse could make me weep fat tears of joy.

     6. I’ve Got My Love to Keep Me Warm, Frank Sinatrarat pack

Such the charmer, Frank Sinatra. He & his girl could be in a blizzard, but he’s so in love, he’s feeling as toasty as can be. Who doesn’t want a little bit of that whimsy on their playlist?

  1. Jingle Bells, Ella Fitzgeraldella fitz

Ella Fitzegerald’s voice continues to be such a gift to jazz music. Jingle Bells can be a tired song, but she makes it worthy for a Gatsby party.

  1. Ave Maria, Josh Groban

I originally wanted this song played at my wedding, but we ended up opting for his version of The Prayer instead. But if we ever renew our vows in an old, Italian chapel, you better believe this song will play. Seeing him sing this live is on the bucket list.

  1. Carol of the Bells, David Crowder Banddcb

David Crowder & his team can jam. That’s all.



  1. Very Merry Christmas, Dave Barnesdave barnes

This is usually the first Christmas song of the season I listen to. It makes me excited to travel, to see family, & be thankful for the ordinary things this season brings. This song also makes me want a big family because it just seems to say the more the merrier!

  1. Thankful, Josh Groban

All-year life inspiration. That’s what this song is. And it’s Josh Groban’s voice, so it basically couldn’t get any better.

  1. Santa Claus is Coming to Town, Bing Crosbybing crosby

Bing teams up with the Andrews Sisters for this fun diddy, & it’s just delightful, really. I would do nearly anything to go back in time to sit in on this show.

  1. A Marshmallow World, Frank Sinatra

The title of the song gives a pretty good indication to the jolliness ahead. Plus, I love that at the end, they have some dialogue to the audience recorded. It’s like we’re there!

  1. Have Yourself a Merry Little Christmas, Judy Garland (on the Louis Armstrong album listed above– two birds, one stone!)

Nobody sings this song like Judy Garland. Watching her sing it in Meet Me in St. Louis makes it even better. Have you seen The Family Stone? That part of the film is in this movie too, at the end, & it’s the sweetest part of the whole movie.

  1. Glory In the Highest/O Come Let Us Adore Him, Shane & Shanedownload

Even though these are technically two separate songs, the first rolls right into the second, & they complete each other. Kind of like Folk Angel, Shane & Shane make this a full-on opportunity to worship & meditate on the goodness of this season.

Bonus Throwback Hits that are near & dear to my heart. YOU’RE WELCOME.

  1. Santa Claus Lane, Hilary DuffHilary_Duff_-_Santa_Claus_Lane
  2. Merry Christmas, Happy Holidays, N’Sync
  3. Baby, It’s Cold Outside, Jessica Simpson & Nick Lachey (#tear)


What Christmas songs do you love that I need to hear? Tell me!


  1. mlbncsga on December 3, 2015 at 2:00 pm

    A’Soulin….Peter Paul and Mary

    • James Chambless on December 5, 2015 at 12:16 am

      I love you so much, my favorite Marsha. I’ve been missing CSGA and all of you all day long.

      • mlbncsga on December 8, 2015 at 2:13 pm

        I Love You Mornin Glorie…finding unexpected comments from you really makes me happy!

  2. James Chambless on December 4, 2015 at 8:22 pm

    I am kind of grinchy about Christmas music. I am the silent minority about it around here though. Once the xm radio stations come on, it’s a short slide from “daddy doesn’t like it” to “I don’t care what you like. It’s Christmas.” I do love singing Christmas carols though. And we have a new tradition around here. We have watched White Christmas every year for so long that we all know the dialog by heart. So now, to liven things up, we all take a part and we act it out while it’s on. We dance, we sing, we laugh a lot. May your days be merry and bright, friend.

    • jenna winegeart on December 4, 2015 at 9:34 pm

      This is awesome! I never saw White Christmas until a few years ago, & it’s definitely become a tradition of ours. That’s such a fun idea. And yes…Christmas music tends to be something people love or hate/strongly dislike/quickly become annoyed by. For me, it fuels my heart to love a little better– other people, like yourself, may not need it. I’d be interested to know what kind of music (if any) fills the playlist of James Chambless.

      • James Chambless on December 5, 2015 at 12:17 am

        My musical interests are wide, varied and (apparently) a constant source of surprise to my friends. =)

  3. Patti Eden on December 4, 2015 at 9:38 pm

    How about some Michael Buble? Just about any on his album “Christmas” is golden.

    • jenna winegeart on December 4, 2015 at 10:28 pm

      I so enjoy Michael Buble but for some reason do not own his Christmas album! He’s on the list now, thanks to you.

  4. sarabface on December 15, 2015 at 4:18 am

    O M G, Jessica & Nick! TOTALLY forgot they were together.

    • jenna winegeart on December 16, 2015 at 1:57 am

      RIGHT?! I died a little the day their relationship did.

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