The Ultimate Holiday Playlist for 2020 — A Mix of Old and New and Local

When it comes to the holidays, choosing the perfect soundtrack is a must. The tradition of seasonal music is a genre unto itself, stretching from the standard classics of crooners like Bing Crosby to today’s diverse array of reworked and original holiday tunes. In hopes of giving you more time to bake gingerbread men and spike the eggnog, we’ve compiled a playlist featuring five new seasonal hits and ten all-time classics, plus some local talent.


“Snow in California” — Ariana Grande (Christmas Kisses EP, 2013)

A love song disguised as a letter to Santa, “Snow in California” finds pop superstar Ariana Grande hoping for an unlikely blizzard to keep her love from leaving. The faint sounds of jingle bells underscore Grande, who sings with sultry, tender conviction as demands of Saint Nick, “What happened to the plan we had? I checked the news and it said It’d be a sunny day.”

“You’re a Mean One, Mr. Grinch” — Aimee Mann (One More Drifter in the Snow, 2006)

For as long as holiday music has existed, it has been covered and reimagined by new generations of artists. While “You’re a Mean One, Mr. Grinch” first premiered back in 1966 as part of the cartoon special Dr. Seuss’ How the Grinch Stole Christmas!, things are kicked into overdrive in Aimee Mann’s playful take, which features Grant-Lee Phillips as the titular green meanie.

“I Saw Mommy Kissing Santa Claus” — Dolly Parton (A Holly Dolly Christmas, 2020)

Country legend Dolly Parton adds a fresh of dash of spice to this sweet tale of a child mistakenly thinking mom is cheating on dad with Kris Kringle. Delivered with Parton’s vibrant twang, the mock horror of a kid spying a Christmas Eve smooch is captured perfectly by the ten-time Grammy winner.

“That Was the Worst Christmas Ever!” — Sufjan Stevens (Songs for Christmas, 2006)

For balance alone, not every holiday song can be cheery. One artist who has taken this belief to heart is Sufjan Stevens, who has released an estimated 100 Christmas-related songs over the course of his career. While many are covers, it’s his originals that truly shine. “That Was the Worst Christmas Ever!” is a quiet, darkly gorgeous song about a Christmas gone awry. Come for the banjo, stay for the feels!

“Wonderful Christmas Time” — The Shins (Holidays Rule, 2012)

One of the standouts on the 2012 compilation album Holidays Rule is a new take on Paul McCartney’s incessantly happy “Wonderful Christmas Time.” One of the few holiday hits to emerge from the era, this 1979 seasonal earworm could easily go sappy in the wrong hands. Fortunately, The Shins’ James Mercer has the vocals to match McCartney’s upbeat falsetto, making for a delightful cover of a modern Christmas mainstay.


“All I Want for Christmas Is You” — Mariah Carey

Released in 1994, this smash-hit from Mariah Carey finally topped the Billboard Hot 100 for the first time ever last year. That’s staying power.

“Little Saint Nick” — The Beach Boys

Leave it to the Beach Boys to make a song about Santa’s ride. Impossibly catchy, just try not to sing along when the “run run reindeer” harmonies start.

“Christmas (Baby Please Come Home)” — Darlene Love

The powerhouse that is Darlene Love could never be captured in a single song, but this one comes close, blending the Phil Spector “wall of sound” with Love’s triumphant vocals.

“Rockin Around the Christmas Tree” — Brenda Lee

Get this: Brenda Lee was only 13-years-old when she recorded the vocals for “Rockin Around the Christmas Tree.” Now, over fifty years later, the track has surpassed over 25 million copies sold. It’s an all-timer.

“Feliz Navidad” — José Feliciano

One of the most unabashedly cheery holiday songs you’ll likely find, the message of José Feliciano’s “Feliz Navidad” is charmingly simple: he wants to wish you a Merry Christmas. Who could refuse?

“Have Yourself a Merry Little Christmas” — Judy Garland

First sung by Garland in the 1944 film Meet Me in St. Louis, “Have Yourself a Merry Little Christmas” has spawned countless covers but none can overtake the glorious original.

“Blue Christmas” — Elvis Presley

Elvis Presley sang a lot of Christmas songs, but it’s “Blue Christmas” that best captures the Graceland star’s ability to toe the line between woe and hope in the bend of a note.

“Santa Claus Is Coming to Town” — Bruce Springsteen

Bruce Springsteen’s infectious enthusiasm for the arrival of Old Saint Nick carries this rollicking rendition of the timeless classic. When the Boss tells you to be good, you better listen.

“Santa Baby” — Eartha Kitt

Eartha Kitt keeps things hot and heavy as she tells Santa about all of the fine things her good behavior should earn her this Christmas. 

“Run Rudolph Run” — Chuck Berry

From the first lick of guitar, this Chuck Berry barnblazer is just the ticket for any holiday playlist with sagging energy to kick things up a notch.

Local Talent

Michelle Schmitt Band Holiday Playlist

In lieu of their annual year-end benefit concert, they’ve created a Benefit Concert playlist (Spotify, Apple Music) and a Michelle Schmitt Holiday playlist (Spotify, Apple Music). For every song downloaded or streamed from these playlists through December 25th, they will donate $5 to Little Wishes.

“Grandma Got Run Over by a Reindeer” — Elmo & Patsy (Dr. Elmo’s Twisted Christmas, 1979)

This chucklesome (and troubling) Christmas song is bound to entertain everyone from ages 4 to 104.

“Merry Christmas, Baby” — Bonnie Raitt & Charles Brown (A Very Special Christmas 2, 1992)

A soulful and smooth rendition of the 1960’s R&B Christmas classic.

“Santa’s Going South for Christmas” — Sammy Hagar (2017)

This hard rock musician switches it up for his ode to warmer weather during the holidays.

“Posada (Pilgrimage to Bethlehem)” — Santana (Platinum Christmas Compilation, 2000)

Best for winding down the night, this is Santana’s only holiday song. A classic guitar solo with some holiday flair.

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Zack Ruskin Zack Ruskin writes on music, cannabis, and culture. His bylines include Vanity FairBillboardEntertainment WeeklyVarietyMerry Jane, and the San Francisco Chronicle. He lives in San Francisco with his wife, Danielle, and their cat, McCovey.