Best Christmas Songs Playlist: 30 Tracks Worth Repeating

Most Christmas playlists are 90% garbage. The same 15 songs on loop from November 1st to December 25th — Mariah in every store, "Last Christmas" in every restaurant, "Jingle Bell Rock" in every elevator. Here's a playlist that skips the obvious and includes the tracks that actually sound good in your house, broken into sections so you can mix depending on your mood.

The Classics That Actually Hold Up

1. "Have Yourself a Merry Little Christmas" — Frank Sinatra. The definitive version. Judy Garland's is sadder, but Frank's is the one you want on in the background.

2. "The Christmas Song" — Nat King Cole. Chestnuts roasting. The man's voice is like a warm blanket.

3. "Sleigh Ride" — The Ronettes. The Phil Spector wall of sound applied to Christmas is the best thing that happened to the genre. This version bounces.

4. "Let It Snow" — Dean Martin. Easy, warm, no drama. Good for cooking.

5. "White Christmas" — Bing Crosby. The best-selling single of all time for a reason. Simple and perfect.

6. "Christmas (Baby Please Come Home)" — Darlene Love. Also from the Phil Spector Christmas album. The most energy of any classic Christmas song.

7. "Rudolph the Red-Nosed Reindeer" — Burl Ives. The stop-motion special version. Brings back being 7.

8. "Blue Christmas" — Elvis Presley. The only sad Christmas song that's actually good.

9. "Rockin' Around the Christmas Tree" — Brenda Lee. She was 13 when she recorded this. It still sounds fresh.

10. "It's the Most Wonderful Time of the Year" — Andy Williams. The original. Not the Andy Williams cover of himself — the actual original recording.

Modern Songs Worth Repeating

11. "All I Want for Christmas Is You" — Mariah Carey. Overplayed, yes. But it's the best modern Christmas song and it's not close. The vocal is extraordinary.

12. "Fairytale of New York" — The Pogues ft. Kirsty MacColl. The best Christmas song ever made, if you're asking me. It's messy, it's sad, it's beautiful, and it's Irish. The Shane MacGowan and Kirsty MacColl duet is devastating.

13. "Last Christmas" — Wham! Yes, it's everywhere. Yes, it's still good. The production is perfect 80s pop.

14. "Christmas Wrapping" — The Waitresses. A great story song. Underrated in the US, huge in the UK. The saxophone break is the moment.

15. "Step Into Christmas" — Elton John. Upbeat, catchy, sounds like what it feels like to have a good Christmas.

16. "Merry Christmas Everyone" — Shakin' Stevens. Huge in the UK, less known in the US. It's a banger. Look it up.

17. "Driving Home for Christmas" — Chris Rea. Another UK classic. The chorus makes you want to be in a car with your family.

18. "River" — Joni Mitchell. "I wish I had a river I could skate away on." The saddest Christmas song. Beautiful.

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19. "That's What I Want for Christmas" — Marvin Gaye. Motown did Christmas well and this is one of the best.

20. "Run Rudolph Run" — Chuck Berry. Rock and roll Christmas. The guitar work is classic Chuck.

Jazz and Soul for the Evening

21. "My Favorite Things" — John Coltrane. Not technically a Christmas song, but it shows up on every jazz Christmas playlist and it fits. Coltrane's version is the one.

22. "Winter Wonderland" — Ella Fitzgerald. Her voice makes everything sound better. This version swings.

23. "Santa Claus Is Coming to Town" — The Jackson 5. Young Michael Jackson at his best. The energy is unmatched.

24. "This Christmas" — Donny Hathaway. The soul Christmas standard. The arrangement is gorgeous. If you only add one new song to your playlist, make it this one.

25. "Merry Christmas Baby" — Charles Brown. Blues Christmas. The guitar and piano are perfect. For late in the evening.

26. "The Little Drummer Boy" — Johnny Cash. The only version of this song that doesn't make me want to skip. Cash's voice gives it gravity.

A Few Odd Ones

27. "Christmas Time Is Here" — Vince Guaraldi Trio. From A Charlie Brown Christmas. The opening piano sets the entire mood of the season in 30 seconds.

28. "I Saw Mommy Kissing Santa Claus" — The Jackson 5. Another young MJ one. Fun and weird.

29. "Merry Xmas Everybody" — Slade. The UK Christmas anthem. Glam rock Christmas. It's loud and silly and perfect.

30. "A Sad Christmas" — Sam Cooke. Slow, beautiful, and a reminder that Christmas isn't happy for everyone.

How to Use This Playlist

Don't play all 30 at once. Make three short playlists:

• Morning: the classics and the upbeat ones (1-10, 11-20)
• Evening cooking: the jazz and soul (21-26)
• Late night: the sad ones and the odd ones (18, 25, 27, 30)

Don't shuffle the whole list. The mood jumps around too much. A good playlist has an arc, not a random selection.

Don't start playing Christmas music before Thanksgiving. A little discipline keeps it from getting stale by December 20th.