- Alvin and The Chipmunks - The Chipmunk Song (Christmas Don't Be Late)
Released in 1958
Genre: Novelty Christmas Song
Composers: Ross Bagdasarian (as David Seville)
Vocalists: Alvin and the Chipmunks (Ross Bagdasarian with sped-up vocals) Ross Bagdasarian created the iconic "chipmunk" voices by singing the song at a slower speed and then playing it back at a higher speed.
- Andy Williams - It's the Most Wonderful Time of the Year
1963
Genre: Traditional Christmas
Originally written in 1962 for the musical "Here's Love," a stage version of the film "Miracle on 34th Street."
Andy Williams' recording of the song was featured in the iconic 1963 animated film "Rudolph the Red-Nosed Reindeer,".
- The Beach Boys - Little Saint Nick
Genre: Christmas, Rock
The Beach Boys' Christmas Album (1964)
The song was originally released in 1963 and reached number 3 on Billboard's Christmas Singles chart.
- Bing Crosby - White Christmas
1942 (Originally from the film "Holiday Inn")
Best-selling single of all time, having sold over 50 million copies worldwide.
- Bing Crosby (ft. Carol Richards) - Silver Bells
1950
Genre: Christmas, Pop
Originally written for the Broadway musical "Stop Dancing," but became a hit after Bing Crosby and Carol Richards' recording was released in 1950.
Reached number 1 on Billboard's Hot 100 chart in 1951, solidifying its status as a holiday classic
Released in 1957
Genre: Christmas, Rock and Roll
Became an instant hit upon its release in 1957, reaching number 6 on the Billboard Hot 100 chart.
Has remained a Christmas staple ever since
- Brenda Lee - Rockin' Around The Christmas Tree
Released in 1957
Genre: Christmas, Rock and Roll
Instant hit upon its release, reaching number 14 on the Billboard Hot 100 chart
- Gene Autry - Frosty The Snowman
Released in 1950
Genre: Christmas, Novelty
Became an instant hit reaching number 1 on the Billboard Hot 100 chart
Originally written for a children's television show, but became so popular it was released as a single
- <a href="/@taskmaster4450le/re-leothreads-w4yxbak8>Dean Martin - Let it Snow
Released: 1945 (Originally by Vaughn Monroe)
Genre: Christmas, Traditional Pop
Let it Snow was originally written by Jule Styne and Sammy Cahn in 1945 and was first recorded by Vaughn Monroe. However, Dean Martin's 1959 recording is arguably the most iconic and widely recognized version.
- Dean Martin - Winter Wonderland
Title: Walking in a Winter Wonderland
Artist: Dean Martin
Genre: Christmas, Traditional Pop
Year: 1964 (originally by Felix Knight and Arthur Schwartz in 1934)
The song's opening line, "Sleigh bells ring, are you listening," was originally "Silver bells ring," but songwriter Schwartz changed it to avoid confusion with another Christmas classic.
- Elvis Presley - Blue Christmas
Year: 1960
Composer and Lyricist: Billy Hayes and Jay W. Johnson
Originally written in 1947 and first recorded by country singer Doyle O'Dell. However, Elvis Presley's 1960 rendition is the most popular and widely recognized version.
- Judy Garland - Have Yourself a Merry Little Christmas
Originally sung in the film "Meet Me in St. Louis"
Genre: Christmas, Ballad
Year: 1944
Composers: Hugh Martin and Ralph Blane
The song has been covered by numerous artists, each adding their own interpretation, but Judy Garland's version remains the most iconic and emotionally impactful.
- José Feliciano - Feliz Navidad
Released in 1970
Genre: Christmas, Latin Pop
Became an instant hit upon its release in 1970, reaching the top 10 on the Billboard Hot 100 chart and becoming one of the most popular Christmas songs in the world.
Feliciano wrote and recorded Feliz Navidad in a single night, inspired by his Puerto Rican heritage and his desire to create a Christmas song that everyone could enjoy.
Thanks to 
There are many more to enjoy besides the favorites I chose for this list.