Penn and I have a good marriage, maybe even a great one. But one thing that will always start a fight in our house is the timing and frequency with which I play Christmas music. I’ll admit I’ll crank a Mariah Carey Christmas classic in September if I’m having a stressful day. My husband? He only wants to hear it after Thanksgiving and, even then, he is particular.
So this is a Penn-approved playlist that’s on repeat in our house now that we are securely in December. It’s a mix of classics, modern covers, and, of course, Miss Kelly Clarkson. It’s mostly upbeat because I’m an easy cry this time of year. Crank this for your holiday party, making cookies, or if you’re doing Santa’s dirty work and wrapping gifts late at night.
1. Fairytale of New York – The Pogues This is Penn’s personal favorite. Some language can be iffy for young ears. If you’d prefer there’s a version featuring Taylor Swift’s boyfriend and his brother.
2. Merry Christmas – Ed Sheeran, Elton John It’s hard to write a new Christmas song but this one is a true bop.
3. Underneath the Tree – Kelly Clarkson If I’m being honest, I could just listen to this album straight through, no skips. But alas, a playlist requires variety. More Kelly to come later in the list. I promise.
4. The 12 Days of Christmas (Live) – Straight No Chaser
The original version of this song can … linger. This acapella version will leave you laughing.
5. Christmas Is All Around – Billy Mack You’ll know this one from the movie Love Actually.
6. Christmas Wrapping – The Waitresses This is Lola’s favorite, upbeat Christmas song to blast on the way to school.
7. Rockin’ Around The Christmas Tree – Brenda Lee I recently learned that Brenda Lee was 13 years old when she recorded this song. I have no idea why she sounds like she’s smoked 3 packs a day but we thank her for creating a classic.
8. Candy Cane Lane – Sia Another “new” Christmas classic!
9. Merry Christmas From The Family – Robert Earl Keen This is the song I learned about in college. I have very distinct memories of singing this at the top of my lungs that last day of finals before Christmas break. Don’t worry mom, I was totally sober.
10. Christmas In Hollis – Run D.M.C.
Die Hard movie lovers will recognize this one. I made a mixtape of Christmas music I recorded off the radio when I was in elementary school and this was missing the first few measures. It was still amazing.
11. The Chanukah Song – Adam Sandler Obviously not a Christmas song but it’s a holiday classic.
12. Wonderful Christmastime – Paul McCartney
13. Santa Claus Is Coming To Town – The Jackson 5
14. You Make It Feel Like Christmas – Gwen Stefani, Blake Shelton This relationship will always confuse me but I will say this song is a fun one.
15. Have Yourself a Merry Little Christmas – James Taylor Being from North Carolina, we are massive James Taylor fans. More from him later in the list.
16. Christmas (Baby Please Come Home) – Michael Buble Did you think we’d get through this whole playlist without a Buble mention?
17. Joy to the World (with the Georgia Mass Choir) – Whitney Houston One of the greatest voices of my generation with a gospel choir? Yes, please.
18. Jingle Bells? – Barbra Streisand
19. Blue Christmas – Elvis Presley This one is a little slower but it seems criminal not to mention it.
20. Feliz Navidad – Jose Feliciano
21. All I Want for Christmas Is You – Mariah Carey Mariah has made this song the national anthem of the holiday season. She quite literally posts a video every year on November 1st of her “thawing.” I think it’s legally required to have this song on a Christmas playlist.
22. Do They Know It’s Christmas? – Band Aid
23. Here Comes Santa Claus – Bing Crosby Is the whole party stopping to sing along now?
24. Christmas Tree Farm – Taylor Swift I think my daughter might be upset if I didn’t include our girl Tay-Tay.
25. Please Come Home for Christmas – Kelly Clarkson Told you she would be back. It really took a lot out of me not to put more Kelly on here.
26. Santa Tell Me – Ariana Grande Ariana, what are you doing here? Oh yes, keeping the party energy up.
27. Run Run Rudolph – Chuck Berry
28. (It Must’ve Been Ol’) Santa Claus – Harry Connick, Jr.
29. What Christmas Means To Me – Stevie Wonder How’s the party going? They better have complemented your playlist already.
30. White Christmas – Michael Buble, Shania Twain Buble has done this song with a few artists but I had to give some love to my girl Shania.
31. Oh Santa! – Mariah Carey, Ariana Grande, Jennifer Hudson
32. Who Comes This Night – James Taylor
33. Step Into Christmas – Elton John
34. Linus and Lucy – Vince Guaraldi Trio Are you instantly transported to A Charlie Brown Christmas or is it just me?
35. Mele Kalikimaka – Bing Crosby
36. Santa Baby – Eartha Kitt We won’t delve into the lyrics on this one, but we can give some praise to Eartha’s sultry vocals.
37. What Christmas Means To Me – Hanson
The Midwest Neighbor is obsessed with this one.
38. Grandma Got Run Over By a Reindeer – Elmo & Patsy
39. Happy Xmas (War Is Over) – John Lennon, Yoko Ono
40. Mistletoe – Justin Bieber
41. Last Christmas – Wham! I’m ending with this song because it’s a bit slower and quite sad. Also, you’ve probably heard it about 263 times already playing over the sound system in every single store.
