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A Guide to the Perfect Holiday Playlist

Timeless tunes to keep your spirits bright all season long.
Popular artists like Wham, Mariah Carey, and Michael Bublé can be heard every winter season.
Popular artists like Wham, Mariah Carey, and Michael Bublé can be heard every winter season.
Juliet Wei

Picture this: you’re curled up in a cozy living room, sipping hot chocolate as snow falls outside. What better way to complete the moment than with a holiday playlist that perfectly captures the season’s magic? Instead of scrolling endlessly through Spotify, let this guide help you craft the ultimate soundtrack for your winter days. 

Did you know that one of the most beloved holiday songs has roots in our community? The timeless classic “Santa Claus is Coming to Town” was written in 1934 by Haven Gillespie and Fred Coots. Its local connection is especially meaningful: Coots’s daughter, a Murray Avenue School student, performed it at a school musical. The song has since been covered over 200 times in countless styles, making it a perfect addition to your playlist.  

Another must-have is “Sleigh Ride” by Leroy Anderson, composed in 1948. Its festive, wintry imagery captures the essence of the season, which is why it’s been performed annually by Mamaroneck High School’s band for the past 55 years. 

Band director Timothy Hooker explains, “It’s actually very hard to play rhythmically, but once it’s on its feet, it’s really fun for the band.” Adding this nostalgic piece to your playlist will bring the warmth of tradition into your holiday season—and if you want to hear it live, don’t miss the Winter Concert! 

Covers also play a big role in holiday music, and Icelandic singer Laufey’s lively rendition of “Santa Baby” brings a fresh twist to the genre. Originally sung by Eartha Kitt in 1953, Laufey’s version features upbeat harmonies and a festive energy that’s perfect for modern playlists. Her talent as a multi-instrumentalist and vocalist makes her interpretation a standout. 

Other covers include Dolly Parton’s “Hard Candy Christmas.” This heartfelt song offers a touch of country charm and resonates with listeners like Ashley Cosiver (’26), who calls it a “classic in [her] family around the holidays.” Its wholesome message and unique style make it an ideal choice for anyone looking to add variety to their playlist. 

Another timeless favorite is “Christmas Time is Here” by the Vince Guaraldi Trio from A Charlie Brown Christmas (1965). Its gentle melody and nostalgic warmth evoke the joy and innocence of Christmas mornings. Emelie Jones (’28) shares her love for “Linus and Lucy” from the same film, describing it as “happy, festive, and reminds [her] of hot chocolate.” For Jones, watching A Charlie Brown Christmas every year is a cherished tradition, and she encourages others to revisit the classic for a dose of holiday cheer. 

With these songs, your holiday playlist will be full of joy, nostalgia, and seasonal spirit. Grab a warm sweater, a steaming cup of cocoa, and let the music set the perfect mood for this magical time of year. Whether you’re reminiscing about the past or discovering new favorites, these tracks are sure to make the season brighter.

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