1990s Holiday Music Is The Perfect Nostalgia Storm

Holiday music has existed for hundreds and hundreds of years, from ancient hymns sang by devoted believers to BTS singing “Santa Claus Is Coming To Town.” Some of it is moving. Some of it is terrible. Actually, a lot of it is terrible, and if I have to hear “Little Drummer Boy” one more time, I’m going to just cancel Christmas.

But there’s this one type of holiday music I can’t get enough of: basically any Christmas song that dropped in the 1990s. Let me set the scene: the elder millennials are old enough to understand and enjoy Christmas fully, but also young enough to still sort of believe in Christmas magic. At the same time, some of the best artists ever are at the height of their careers, and many of them take a minute of their time to record a holiday song or two.

In other words, ‘90s holiday tunes are the perfect nostalgia storm, and it will never, ever get old for me.

Below, I’ve listed a few all-time favorites. The absolute must-have ‘90s jams of the season. And if you scroll to the bottom, I’ll hook you up with the complete ‘90s playlist I listen to on Spotify that has dozens more songs. Ready?

“All I Want For Christmas Is You” by Mariah Carey

This is the all-time GOAT of all Christmas songs ever in the history of time, so it follows that this holiday bop is also the best of the ‘90s, too. Everything is perfect: the lyrics, the music video, and of course Mariah’s voice. There’s a reason it’s called #MariahSZN.

“Silent Night” by Sinead O’Connor

Honestly, this is the only version of “Silent Night” that I ever want to listen to. It’s so magical and eerie with Sinead lending her gentle fairy-like voice to this atmospheric rendition. Almost nothing compares 2 it. Especially in a year when we lost such a special and powerful voice in music, this is a must-listen.

“If Everyday Could Be Christmas” by 98 Degrees

Are those angels singing, or is it just boy band 98 Degrees showing exactly what they can do with their voices when they celebrate the holiday?

“Song For A Winter’s Night” by Sarah McLachlan

A key voice of the 90s, would any holiday complication from this decade be complete without the Lilith Fair founder? Love the layering of her voice in this tune, and the full-on wintertime feel she captures. And there are some very 90s doo-doo-doot-doos in there, too.

“Please Come Home For Christmas” by Jon Bon Jovi

There are a few good versions of this classic, “Please Come Home For Christmas,” but do any of them truly have the ‘90s spirit of this one? I love the original by Charles Brown, and the 1978 cover by the Eagles, but this version has a special feel that reminds us all of our favorite era of slap bracelets and bucket hats.

“Just Like Christmas” by Low

There are a lot of pop songs, divas, and boy bands on this playlist (as there should be) but what about all of the lo-fi indie rock that was being created throughout the 1990s? There was a lot of it, and while some bands were way too cool to record holiday hits (I’m looking at you, Nirvana), some indie outfits took up the challenge. One amazing independent label band even took the time to make an entire album, and it is completely awesome. Boy-girl duo Low (made up of Alan Sparhawk and Mimi Parker) released “Christmas” in 1999 and it’s been a staple of holiday listening for millions ever since.

“Chanukah Song” by Adam Sandler

Did I mention that arguably the best Chanukah song of all time was also released in the 1990s? Adam Sandler sang it for the first time on Saturday Night Live’s Weekend Update in 1994, and it doesn’t get more nostalgic than that. It’s funny, it’s catchy, and it also lists some of the best Jewish people of the 90s. If it’s not on your holiday playlist you are messing up.

“Christmas In The City” by Mary J. Blige

We also definitely need some classic old school-style rap on our mix, and Mary J. Blige is here to help. I love this song so much; it’s an original tune that has everything you could want from an R&B selection. Totally underrated holiday tune.

“Santa Claus Is Coming To Town” by Michael Bolton

Michael Bolton and his magical blond ponytail had the best decade ever in the 1990s. And at the height of his (and his ponytail’s) fame, he released his very own Christmas album, This Is The Time, in the winter of 1996. It has quite a few memorable songs on it, and you might be most familiar with his version of “White Christmas,” but my favorite is definitely “Santa Claus Is Coming To Town.”

“The Christians And The Pagans” by Dar Williams

We also need some indie folk on our holiday list, and Dar Williams, one of the most talented folk song writers of the ‘90s, is here for it. This is a classic feel-good narrative song about a family coming together for the holidays even though they celebrate differently. Hey, maybe this could stop an argument about politics at the dining room table?

“Baby, It’s Cold Outside” by Vanessa Williams and Bobby Caldwell

There have been tons of covers of this song since its original release in 1949. And right now the most popular version is probably the duet between Idina Menzel and Michael Bublé — but let’s not forget the vital 1996 recording of Vanessa Williams and Bobby Caldwell. Yes, there’s a little bit of controversy surrounding the song’s themes and sexual consent, but it seems like there’s a feminist reading that holds water, too.

“Sleigh Ride” by TLC

While one of the coolest groups of the ‘90s were working on their masterpiece, CrazySexyCool, they put aside just a little bit of time to record a Christmas song in 1993. The result is “Sleigh Ride,” and it is delightful. No word on if Santa is a scrub, but we do know he has his own ride.

“Let It Snow” by Boyz II Men, featuring Brian McKnight

I danced my first slow dance to Boys II Men (“End of the Road,” if you must know) and they defined the ‘90s in ways like that for most everyone. They also teamed up with fellow ‘90s superpower Brian McKnight in 1993 to record “Let It Snow,” to bring joy to everyone at Christmastime. Also, you just absolutely have to watch this music video. The holiday sweaters alone are too much.

“The Ice Of Boston” by The Dismemberment Plan

This one goes out to the people who spent most of the 1990s wearing a dirty flannel, skate shoes, and greasy hair. Indie rock bands create Christmas music, too, sometimes. Sure, this isn’t the super-polished, harmonized pop songs that we think about at first, but there’s a place for this jam, too. I love the roughness — and the reminder that not everything about the holidays is perfect. There’s ice, for starters.

“Winter Wonderland” by Jewel

Jewel ruled the ‘90s and all of her talents are highlighted on her amazing version of “Walking In A Winter Wonderland.” For example — and I am not kidding — she yodels in this song. And it is wonderful. Don’t believe me? Just listen.

“Have Yourself A Merry Little Christmas” by Tori Amos

She put out an excellent, full Christmas album, Midwinter Graces, in 2009, but way back in 1998, Tori Amos put out this B-side to “Spark”, her first single off of From The Choirgirl Hotel. It’s sweet and just a little dark, for all those who like to celebrate with a bit of angst and witchiness.

“Christmastime” by The Smashing Pumpkins

This song is surprisingly good compared to any of The Smashing Pumpkins’ hits, and it’s honestly one of my all-time favorite 90s holiday songs. There’s a rumor that Billy Corgan and friends recorded a complete Christmas album in Billy’s basement during the pandemic and... until that surfaces somehow, we still have this hit from 1997.

While all of the above 90s holiday jams are absolutely necessary, I have many, many more for you, including Hanson, Tracy Chapman, NSYNC, Hootie and the Blowfish, Amy Grant, Gloria Estefan, Enya, Run DMC, Spice Girls, and more. Below, find Scary Mommy’s complete Spotify playlist of 90s Christmas songs. Merry Christmas, Happy Holidays, and Happy New Year!