Matt Knight

Matt Knight

Matt Knight

Now, let’s start this list off by saying that this is my OPINION and we all know music is subjective. There will be some songs left off this list that probably go on yours and vice versa.

That being said, let’s get into what I think are the best 10 Christmas/Holiday songs of all time.

…and don’t forget to listen to the 100.1 Hours of Christmas on ‘JRZ starting December 21st at 5pm, where all of these songs and lots more will be taking you all the way through Christmas day.

  • 10 - "Step Into Christmas" Elton John (1973)

    How can you not feel extra Christmas-y when Elton John is telling you to literally STEP INTO CHRISTMAS! “Step into Christmas” was mixed to sound like one of producer Phil Spector’s 1960s recordings, using plenty of compression and imitating his trademark wall of sound technique. This was intentional according to both  Elton John and Bernie Taupin, and an homage of sorts to Christmas songs by Spector-produced groups such as The Ronettes.

  • 9 - "Christmas In Hollis" Run-D.M.C. (1987)

    Run-D.M.C., one of the greatest hip-hop groups of all time, were asked to participate on the album “A Very Special Christmas” to benefit Special Olympics. After first refusing, publicist Bill Adler gave the band the idea for “Christmas in Hollis,” and they changed their minds and agreed to be on the album. 

  • 8 - "Christmas Eve/Sarajevo 12/24" Trans-Siberian Orchestra (1996)

    This song just takes a some classic Christmas songs (God Rest Ye Merry Gentlemen/Carol of the Bells) and ROCKS them. The piece describes a lone cello player playing a forgotten Christmas carol in war-torn Sarajevo.

    Producer Paul O’Neill explained the story behind “Christmas Eve/Sarajevo 12/24” in an interview published on “We heard about this cello player born in Sarajevo many years ago who left when he was fairly young to go on to become a well-respected musician, playing with various symphonies throughout Europe. Many decades later, he returned to Sarajevo as an elderly man—at the height of the Bosnian War, only to find his city in complete ruins.”

  • 7 - "Last Christmas" Wham! (1984)

    “Last Christmas” had its beginnings in 1983, while George Michael and Andrew Ridgeley were visiting Michael’s parents. It was written by Michael in his childhood bedroom. Michael played Ridgeley the introduction and chorus melody to “Last Christmas”, which Ridgeley later called “a moment of wonder.” Coincidentally with the sudden death of George Michael on December 25, 2016, “Last Christmas” reach number 7 on the UK Singles Chart for 5 weeks (December 8, 2016 – January 5, 2017).

  • 6 - "The Christmas Song" Nat King Cole (1946)

    This song has such sentimental value to me as my grandfather LOVED the voice of Nat King Cole. This song takes me back to childhood with Cole’s crooning and singing this to perfection.

    The Nat King Cole Trio first recorded the song in June 1946. At Cole’s behest, a second recording was made in August utilizing a small string section. This version became a massive hit on both the pop and R&B charts. Cole again recorded the song in 1953, using the same arrangement with a full orchestra arranged and conducted by Nelson Riddle, and once more in 1961, in a stereophonic version with another full orchestra arranged and conducted by Ralph Carmichael. Cole’s 1961 version heard below is generally regarded as definitive.

  • 5 - "Happy Xmas (War Is Over)" John Lennon (1971)

    A protest song against the Vietnam War, “Happy Xmas (War Is Over)” was the culmination of more than two years of peace activism undertaken by John Lennon and Yoko Ono that began with the bed-ins they convened in March and May 1969, the first of which took place during their honeymoon. The song was part an international multimedia campaign launched in December 1969 that primarily consisted of renting billboard space in 12 major cities around the world for the display of black and white posters that declared “WAR IS OVER! If You Want It – Happy Christmas from John & Yoko.”

  • 4 - "White Christmas" The Drifters (1954)

    With all due respect to Bing Crosby, this version of “White Christmas” is my absolute favorite. While on tour in 1953, Clyde McPhatter asked Bill Pinkney to write an arrangement of “White Christmas” for the Drifters. Pinkney looked to the 1948 version by the Ravens, a pioneering R&B group that featured bass vocalist Jimmy Ricks as the first lead, followed by falsetto tenor Maithe Marshall. Pinkney said he “jazzed up the vocals” and opened the song with his deep baritone. “Clyde took the high part, the top tenor part,” said Pinkney, “and I came back in after that.”

  • 3 - "Underneath The Tree" Kelly Clarkson (2013)

    Ok, I’m sure you’re thinking this song is too high on a “greatest Christmas songs of ALL TIME list”, but go ahead and listen to it. There’s no way you won’t be singing this in your head for hours after hearing it. This song is an absolute Christmas BANGER. From Kelly Clarkson’s first Christmas album “Wrapped In Red”, she sings of gratitude for companionship during the holidays, in which the loved one is referred to as the only present needed “underneath the tree.”

  • 2 - "This Christmas" Donny Hathaway (1970)

    This song ALMOST overtook my #1 spot but it was hard to make that call so I left it at #2, but really it’s “1A.”

    This is just about the perfect Christmas song with the production, the lyrics…it’s just so incredible. “This Christmas” was released as a single in 1970. It initially saw little success, as it was listed just once on any of Billboard magazine’s weekly published music charts in the 1970s, specifically Billboard’s special Christmas Singles chart. But in recent years, the song has made it onto a number of Billboard’s weekly music charts.

  • 1 - "It's The Most Wonderful Time Of The Year" Andy Williams (1963)

    It literally doesn’t get any better than this one. I will not be swayed on this one! It’s the perfect tune for the holidays.

    The song is a celebration and description of activities associated with the Christmas season, focusing primarily on get-togethers between friends and families. Among the activities included in the song is the telling of “scary ghost stories,” a Victorian Christmas tradition that has mostly gone by the wayside, but survives in the seasonal popularity of numerous adaptations of Charles Dickens’ A Christmas Carol. Other activities mentioned include hosting parties, spontaneous visits from friends, spending time with loved ones, sledding for children, roasting marshmallows, sharing stories about previous Christmases, and singing Christmas carols in winter weather all with the amazing crooning of Andy Williams. PERFECTION!

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