The Christmas season is a time of joy, a time of giving, and a time of fictional artists singing Christmas songs in a variety of musical styles — some timeless, some decidedly less so. Here are ten performances from across the decades showing the wide range of approaches they have taken. I’ve added narrative context to each to give you a more complete yuletide experience. Enjoy!
Bob Wallace, Phil Davis, Betty Haynes, Judy Haynes: “White Christmas” (1954)
Years after the end of the war, a couple of army buddies-turned-successful Broadway performers and producers concoct an elaborate plan to help their former commanding officer, now a Vermont innkeeper with a run of bad luck.
Ricky Nelson: “Jingle Bells” (1960)
A group of college kids celebrate Christmas by inviting their parents and an elderly couple they’ve only just met to the lamest frat party ever. Things get really wild when one of the frat boys breaks out a guitar.
The Monkees: “Ríu Chíu” (1967)
After a long week helping a joyless rich kid learn the meaning of Christmas, four young musicians record a version of a 16th-century Spanish villancico in their swanky Malibu beach house.
The Partridge Family: “Have Yourself a Merry Little Christmas” (1971)
On the night before Christmas, a family band in a kaleidoscope bus break down outside an Old West ghost town. A grizzled miner tells the family a story while the oldest son / lead vocalist fixes the bus. The family thanks the miner by singing this treacly version of a Christmas classic.
Rowlf the Dog with John Denver: “Have Yourself a Merry Little Christmas” (1979)
A former folk singer with boyish good looks visits a dilapidated theater run by a group of animals and monsters. He performs a number of Christmas songs there, including this duet backstage with a scruffy dog piano player.
The California Raisins: “Rudolph the Red-Nosed Reindeer” (1987)
An R&B outfit made up of dried grapes misses the last bus after playing a Christmas Eve gig.
The Chipmunks: “Sleigh Ride” (1990)
A singing group who haven’t had a hit in decades make a bid for relevance by co-opting contemporary Black music and culture.
Spinal Tap: “Christmas with the Devil (Live)” 
A long-in-the-tooth heavy metal group with a history of drummers dying under mysterious circumstances appeals to the overlooked “Satan lover” demographic with this modern-day Christmas classic.
Billy Mack: “Christmas Is All Around” (2003)
A washed-up rock star stages a comeback by squeezing an extra syllable into an old Troggs hit and telling anyone who will listen how truly awful the resulting Christmas single is.
Snoop Dogg ft. Beca Mitchell of the Barden Bellas: “Winter Wonderland / Here Comes Santa Claus” (2015)
A studio intern and leader of a disgraced college a cappella group has an idea to save a recording in progress by the rapper who gave us the album Doggystyle.