It’s the Most Wonderful Time of the Year – Andy WilliamsHas there ever been another Christmas song that so perfectly describes the holiday season in a single lyric? It’s the most wonderful time of the year!2) Rockin’ Around the Christmas Tree – Brenda LeeBrenda Lee’s Christmas ode to our favorite firs has been spun every year since 1958.3) A Holly Jolly Christmas – Burl IvesThis Christmas song is the title track from Burl Ives’ double-sided album, which includes other classics like “The Little Drummer Boy” and “White Christmas.”4) Christmas (Baby Please Come Home) – Darlene LoveIt may be difficult to believe now, but this Christmas song wasn’t a massive hit until years after it was released.5) The Christmas Song – Nat King ColeSomehow Nat King Cole has managed to fit everything that’s magical about Christmas into one song.6) White Christmas – Bing CrosbyThe most iconic Christmas song by the most iconic Christmas singer, this is the best-selling single of all time with more that 50 million records sold!7) Have Yourself a Merry Little Christmas – Frank SinatraEven if it’s just for a moment, this Christmas song helps you feel as though your troubles are miles away over the yuletide season.8) Sleigh Ride – The RonettesThe composer of this key-changing classic actually first came up with the idea for this holiday song during a summer heatwave!9) Carol of the Bells – John WilliamsThe only thing more contentious than the best Christmas song ever is the best Christmas movie ever, but this Christmas carol and the movie this version comes from both have to be up there.10) It’s Beginning to Look a Lot Like Christmas – Perry ComoThis Christmas song proves that some things never really change. For example, moms and dads hardly being able to wait for schools to start again after Christmas. 11) You’re a Mean One, Mr. Grinch – Thurl RavenscroftChristmas music is usually about everything that’s wonderful about that time of the year, so there’s something refreshing about hearing all the delightfully awful ways to describe the Grinch.12) Jingle Bells – Frank SinatraThis Christmas classic started its life as a suggestive 19th century song about an unchaperoned ride in an open sleigh – a pretty big taboo in 1857, but probably appropriate for the king of crooners.13) Feliz Navidad – José Feliciano Fifty years after the release of this Christmas classic, composer José Feliciano said he included the English lyric to ensure the song would be played on English-language radio stations.14) Let it Snow! Let it Snow! Let it Snow!Ol’ Blue Eyes got it right with this holiday song – battling a snowstorm home really doesn’t feel as bad after a night in with that special someone.15) God Rest ye Merry Gentlemen – Bing CrosbyThis Christmas carol is featured on Bing Crosby’s ‘Merry Christmas’ album, which has remained in print constantly since its original release in 1945.16) Santa Baby – Eartha Kitt Santa’s naughty or nice list normally decides whether kids get a doll or a lump of coal. But hopefully Eartha Kitt got her yacht, duplex, and ’54 convertible…17) Cool Yule – Louis Armstrong Sometimes they’re heartfelt, sometimes they’re sad, but never has a Christmas song been so effortlessly cool as this one. 18) (Everybody’s Waitin’ For) The Man with the Bag – Kay Starr When you listen to this Christmas song, it’s almost as though the Big Band Era was created just to make festive tunes.19) Christmas Time is Here – Vince Guaraldi TrioThere were two versions of this song – a vocal and an instrumental – both written for the animated Christmas special “A Charlie Brown Christmas.”20- Caroling, Caroling – Nat King ColeThis Christmas song has the honor of being made famous by Nat King Cole, then again 40 years later by his daughter Natalie Cole.21- Blue Christmas – Elvis PresleyAny list of classic Christmas music isn’t complete without at least one song by The King of Rock and Roll.22- Little Saint Nick – The Beach BoysThere are a lot of Christmas songs about cozy dates, but how many were actually written on a date? Brian Wilson wrote the lyrics while out on a date and then rushed home to finish the music.23- Do you Hear What I Hear? – Bing Crosby Everyone wishes for a bit of tranquillity over Christmas, but the original version of “Do You Hear What I Hear?” was actually written as a plea for peace during the Cuban Missile Crisis in 1962.24- Silver Bells – Bing Crosby“That Christmas falls on the 25th of December every year / So can you be sure that we are going to have Christmas songs” – well, some things don’t change, even with time!25- Winter Wonderland – Darlene LoveWhile Darlene Love’s version of “Winter Wonderland” is one of the most well-known, this holiday song has been recorded by more than 200 different artists.26- Mele Kalikimaka – Bing Crosby, The Andrew SistersMillions around the world are more likely to see palm trees than Christmas trees in December.