10 Classic Holiday Album Covers, Chosen by Al Risi of Groove Guild

Trans-Siberian Orchestra, Ella Fitzgerald and more

"Walking In a Winter Wonderland," reimagined

Hey there Muse, are you listening?
Here's a list, that's worth considerin'
A beautiful sight, make ya feel just right,
Checkin' out Al Risi's list tonight

Now ya know, 'tis the season
Top holiday albums, 'tis the reason
They can be kinda fun, contract fillers for some
Checkin' out Al Risi's list tonight

In the meadow we can build a snowman
We'll pretend he looks just like JAMES BROWN
His "Funky Christmas" is a classic, man
And we sure do miss having him around!

Later on, you'll admire
This holiday list, by the fire
Maybe you won't, and even if you don't
(You're still) checkin' out Al Risi's list tonight

As I persist, with this mission
To rewrite this song, with precision
Trickier than I thought, hope it ain't for naught
Checkin' out Al Risi's list tonight

Another verse, is this the remix?
Feels like a curse, nothing rhymes with remix
But I'll continue on, until I finish this song
Checkin' out Al Risi's list tonight

In the meadow, we can build a snowman
This time we'll pretend he's CHARLIE BROWN
His Christmas Special is a classic, man
It's the best holiday soundtrack around

Please enjoy, this festive season
With those you love, for good reason
Face unafraid, the choices you've made
Checkin' out Al Risi's list tonight!

Various Artists
A Very Special Christmas (1987)

The one that started it all! Love the collaboration with iconic artist/activist Keith Haring, who offered his artwork free of charge for this charitable project. This series, conceived by music legend Jimmy Iovine, has gone on to raise over $100 million for the Special Olympics spanning 10 different releases.

Vince Guaraldi Trio
A Charlie Brown Christmas [Original TV Soundtrack] (1965)

This one is a sentimental favorite since Charlie Brown was a staple of my childhood. It's the characters that make this album cover, but I also love all the white space. Simple, clean and effective. The music deserves a mention here, too. The Vince Guaraldi Trio made a timeless contemporary jazz record that undoubtedly started a love affair with the genre for countless children.

Various Artists
Putumayo Presents: Jazz & Blues Christmas (2008)

This album cover resonates for a number of reasons. First, it represents two great American art forms, both of which are credited to African American culture—jazz and blues—thereby giving much-needed representation within the Christmas album genre. I also love that this album is immediately recognizable as a Putumayo release due to its distinctive album art style that's consistent across all Putumayo releases. The artist, Nicola Heindl, has a "folky modern style" that "represents one of Putumayo's goals: to connect the traditional to the contemporary." Mission accomplished!

Ella Fitzgerald
Ella Wishes You a Swinging Christmas (1960)

This album has been reissued many times over the years with a variety of covers. This one is my favorite. It's fun, colorful and childlike, which is very on brand for Ella, who, by many accounts, embodied a childlike spirit throughout her life.

Everett Bradley
Holidelic: Rebooty (2017)

This album is a companion piece to the beloved perennial holiday funk revue Holidelic that has been gracing NYC stages since 2002 with its "exclusive and inclusive holiday party" magic. Its creator, Everett Bradley, is a Grammy-nominated percussionist whose credits include E Street Band, Bon Jovi and Hall & Oates (to name a few). Perhaps my personal connection with Everett is influencing me here, but this cover not only embodies his spirit but also the spirit of Holidelic. If you want to funk up your Chrstmas playlist, this is the record for you.

Various Artists
New Wave Xmas: Just Can't Get Enough (1996)

AllMusic.com said it best: "Most of the material on the disc is very rare, so the album functions as a convenient way to gather an abundance of offbeat new wave and alternative tracks. The record doesn't really gel into a cohesive listening experience, but as a grab-bag sampler, it's fun." I'd also say the album cover is fun … I mean, look at that flair Santa is rocking!

Erran Baron Cohen
Erran Baron Cohen Presents: Songs in the Key of Hanukkah (2008)

This album cover is pretty simple but also very colorful and expressive. It makes me smile whenever I see it. I will also add that its reimagination of the Dreidel song is a banger!

Trans-Siberian Orchestra
Christmas Eve and Other Stories (1996)

This is the album that put Trans-Siberian Orchestra on the radar of millions of people. It has gone on to become one of the best-selling Christmas albums of all time in the U.S. Edgar Jerins' painting turned cover art perfectly captures the innocence and beauty of Christmas, but that kid's feet must be really cold.

Various Artists
Mr. Hankey's Christmas Classics (1999)

Maybe it's the 10-year-old little boy in me but a Christmas album with poop and a parental advisory sticker is funny. Long live Mr. Hankey!

Jingle Dogs
Christmas Unleashed (1995)

Who's a good boy? Although the album itself is novelty and only amusing on the first listen at best, this album cover brings me joy every time it crosses my gaze. 

*As a bonus, here are a few of the worst holiday album covers in all the land.

Santa's Little Helpers
All I Want for Christmas Is My Two Front Teeth and Festive Favorites for Children (2007)

Who has bigger regrets, this kid or the Nirvana naked baby? Ah, Nevermind!

Bordellmammas Julvisor
(Self-titled, 1972)

I've never been to Sweden, but it sure does look like they celebrate Christmas a bit differently. No judgment, just an observation.

William Hung
Hung for the Holidays (2004)

They say imitation is a form of flattery, but South Park creators should be insulted. Hard no to all of this!

Art of the Album is a regular feature looking at the craft of album-cover design. If you'd like to write for the series, or learn more about our Clio Music program, please get in touch.

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