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Holiday Playlist - Twenty Favorite Songs Over Six Decades

Updated on December 6, 2019
Nella DiCarlo profile image

I'm an online writer with a passion for music and entertainment. I'm an avid and nostalgic fan of music of all kinds.

Silver Bells, Bing Crosby 1950

Beautiful and brings a joyous sense of nostalgia for a simpler era in a wonderful scene.

Jingle Bell Rock, Bobby Helms 1957

This is my favorite version ever of this lively spirited song. Definitely a classic.

Let it Snow, Dean Martin 1959

His voice and the lyrics makes being snowbound sound so romantic and cozy.

Rockin Around the Christmas Tree, Brenda Lee 1960

Fun lyrics, the sound of the saxophone and the energy of this song gets me in the holiday spirit every year. One of my faves.

Christmas Song (Chestnuts Roasting on an open fire) Nat King Cole 1961

A wonderful, gentle classic. The song was originally recorded in 1946, but the version we hear on radio today is from 1961.

Sleigh Ride, Ronettes 1963

This 1960s version by the wonderful American girl group is my favorite. Lots of energy in this song, and makes you feel like you are actually on that sleigh ride!

Feliz Navidad, Jose Feliciano 1970

This is a real nostalgic one for me, as I have frozen the wonderful memory of hearing this song playing on the car radio on many a Christmas Eve as the family head out to visit relatives for the holiday.

Little Drummer Boy

Little Drummer Boy, Bing Crosby and David Bowie 1977

Amazing and unlikely duet. A beautiful moment. Recorded for a Bing Crosby Christmas special, his last.

Mary's Boy Child, Boney M 1978

An upbeat song and a true classic for the season.

Santa Claus is coming to Town, Bruce Springsteen 1978

Always fun to hear this cool live track during the holidays. Puts you in a good mood.

Band Aid

Do they know its Christmas, Band Aid 1984

I remember this being released, and I purchased the 45 on vinyl. So many artists looking good, sounding great and supporting an important cause. Great video!

Baby Please Come Home - U2 1987

Bono sings of longing to be reunited with his love at Christmas time. U2 was at the height of superstardom in 1987 and this song is a classic holiday track for me.

I saw Mommy kissing Santa Claus - John Mellencamp 1987

I heard this one for the first time this season just a couple days back, and it really energizes you. Very upbeat and cool version of the song.

Winter Wonderland, Annie Lennox 1987

This song is just so chill and relaxing.. inspires the imagination to see a pretty version of our winter days. Classic holiday favorite.

All I want for Christmas is You, Mariah Carey 1994

Something from the 90s.. A favorite energetic and highly lucrative Christmas track from the amazing Mariah Carey. Released 25 years ago!

My only wish (this year) Britney Spears 2000

A cute Christmas song released when teenage Britney had just recently become a big star. A modern holiday classic.

Merry Christmas Baby, Sheryl Crow 2008

A selection from the late 2000s. This one I heard this week again after a few years, and it's becoming another modern favorite. Her incredible voice shines as usual.

It's beginning to look a lot like Christmas, Michael Buble 2011

That feeling of nostalgia, along with the legendary voice of Michael Buble contributes to a wonderful modern version of this classic. The entire album is great to listen to during the season

Santa Tell Me, Ariana Grande 2013

Mega star Ariana Grande released this back in 2013, and her vocals were fantastic as always. Cute song, silly video.

Jingle Bells, Gwen Stefani 2017

I was excited that Gwen Stefani released a Christmas album just a couple of years back, and the entire album is energetic, lively and fun. This track is one of my faves.

© 2019 Nella DiCarlo


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