The Most Festive Holiday Playlist

Christmas isn’t a time to settle for pleasant; it’s a time to indulge in all of the merriment you can handle. Christmas compositions reflect that sentiment, so why aren’t arrangements and covers reflecting that, too? ‘Tis the season to celebrate the arrival of the newborn king, the gathering of families, and the hope that a brighter, better future lies ahead.

Worry not – here to help cut through the overly saccharine renditions of “Santa Claus is Coming To Town” is a very special holiday playlist brimming with incredible instrumentals, unexpected embellishments, and sophisticated arrangements.

Leave it to the Oxford English Dictionary to define festive with the most eloquent and accurate language possible – according to the OED, festive describes anything that’s cheerful and jovially celebratory. All that is gleeful and merry. In other words, all that is Christmas.

And Christmas is finally here. Let’s put on all of the ugly sweaters and party!

1. “O Come All Ye Faithful” – Pentatonix

The centuries-old Adeste Fideles may have been written by monks of various order or a Portuguese king – some even claim St. Bonaventure himself penned the Latin words to the ancient melody. While the composer’s identity remains unknown, one things is for sure: the song is a December staple for church services and radio stations alike.

It would make sense for the music to match the lyrics, and “O Come, All Ye Faithful” invites the listener to rejoice. In spite of earnest words, most musical interpretations are quiet at best, and they have not been able to rise to the occasion of Christmas over the years.

So who can arrange “O Come, All Ye Faithful” in a way that echoes the lyrics’ invitation to come and celebrate?

Pentatonix, that’s who.

It took centuries for the world to hear the call to “come, let us adore him” in a way that makes you want to do just that. Thank goodness that Pentatonix sought to infuse their interpretation with merrymaking. The introduction of African rhythms and chanting combined with syncopation and a moderate tempo (111 bpm) evoke a spirit of pure jubilance. And best of all, the song showcases the vocal talents of a gospel choir to add to the festivities in the final buildup and hurrah!

2. “Joy To The World” – Mariah Carey

The most published Christmas hymn in North America also happens to be the most frequently recorded Christmas carol, and nobody instills more joy into this song than Mariah Carey.

She begins the song with soulful vocal stylings – the kind that made her famous – and carries those stylings throughout the song, even as the tempo amps up. This builds interest and excitement, but as we delve into the final third of the song, the party takes a major upswing! A bit of a truck driver’s gear shift and a few quotes from Three Dog Night’s beloved “Joy to the World” provide an unexpected but totally fun twist to this Christmas classic.

Combine that pace with Carey’s vocals and the power of the live gospel choir and you have a hymn rescued from the staleness of repetition. The final stroke of genius is the “amen” chord at the end, a reminder of the gospel feel of the beginning of the tune, and long cadential chord for Mariah to riff over.

3. “White Christmas” – The Drifters

In 1942, Irving Berlin penned this little tune that reflects on the Christmases of yesteryear, and Bing Crosby’s voice carried those wistful lyrics to listeners across America. Since World War II, Crosby’s voice is the one we hear crooning “White Christmas” most frequently on our radio stations, in our television ads, and as background music. That it is beloved by the masses goes without question; however, it’s not necessarily the most joyous of Christmas songs.

The Drifters’ “White Christmas” removes the bittersweetness and replaces it with a delectable dose of optimism and cheerfulness (as seen here). The arrangement in this rendition drives interest by using both the lowest and highest voices in the quartet to deliver the lead lines throughout the entirety of the piece. By pairing the ba-do-ba-do bass and the “aye-aye-aye-I’m dreaming” against the relaxed swing, you just can’t help but bop your head, tap your foot, and grin.

4. “The Man With The Bag” – Kay Starr

Have you done everything you should “extra special good?” I hope you did – you might find coal in your stocking otherwise! In case you didn’t know, “the man with the bag” is good ol’ Santa Claus himself. It’s surprising that this song doesn’t get more airplay in November and December, especially since it was a regular on Billboard’s list of top Christmas songs from the 1950s.

Kay Starr delivers a fun and feel-good tune with her natural jazz accents, and kudos to the arranger for synchronizing the trills in the horns to pretty much match Starr’s signature vibrato. The ascending licks bridge the gap between phrases, and the bop stylings drive us straight into a jazz classic that gets you swinging.

5. “Frosty the Snowman” – Harry Connick Jr.

I always associated Frosty the Snowman with the cartoon special of my childhood and school Christmas concerts: light, fluffy, and meant for kids. After all, the song was recorded after the immense success of Rudolph, another staple in the carols-for-kids list.

Harry Connick Jr.’s album Harry for the Holidays kicks off with this powerful adaptation of Frosty the Snowman. Connick excels at creating a version of “Frosty the Snowman” the whole family can really enjoy. He replaces the saccharine moments and injects the song with a few screaming trumpets, brass duets, and his signature big band and New Orleans sound. A chorus of voices calls you to participate in cheering Frosty on with the “thumpety thump thump, look at frosty go!” I daresay this song has never sounded as exciting or celebratory ever before – no wonder that it took someone from New Orleans to fix that for us!

6. “Jingle Bells” – Frank Sinatra

“Jingle Bells” has been around since 1857 and people around the world have been singing it ever since. The ubiquitous holiday song is usually one of the first holiday songs a child learns, much like “Frosty” and “Rudolph” and others assigned to the kiddie’s canon of Christmas tunes. Understandably, it doesn’t carry much appeal for the grown-up listeners out there, so it doesn’t come as a surprise that Frank Sinatra was the one to hand this song some spiked eggnog and a cigar.

Among other characteristics, what sets this arrangement apart from others is that it uses the vocal chorus as onomatopoeia. The additional vocalists contribute a whole lotta flavor and spice, and when you factor in the actual sleigh bells, swinging beat, and smooth Sinatra voice, this song grows up.

7. “O Tannenbaum” – Vince Guaraldi Trio

Much like many of our modern-day holiday traditions, the world’s most famous German carol didn’t set out to become a Christmas song at all. In fact, “O Tannenbaum” is based on a traditional German folk song. Somewhere along the way, a German songwriter took the melody and penned the accompanying lyrics to celebrate faithfulness as a not-so-thinly-veiled reaction to a lover’s infidelity. We didn’t use trees in our holiday decor until the 19th century, and it was in 1824 that organist Ernst Anschutz wrote the lyrics we know today.

Wait – does anybody out there actually know any of the lyrics beyond “O Christmas tree, o Christmas tree/how lovely are your branches”?

This is one of those rare Christmas tunes where people are much more familiar with the melody than the words. With that in mind, the Vince Guaraldi Trio doesn’t serve up your großmutter’s straightlaced tannenbaum (which means fir tree, by the way). Instead, Guaraldi and friends present a relaxed, whimsical jazz interpretation that doesn’t stray too far from the original melody. The chords and bassline serve to create musical interest that is largely absent in the original composition.

Like a glass of wine by the fire after you’ve spent the entire day getting your house ready for company, this rendition suggests a happy dose of festive relaxation in the face of the holiday rush. Also, #charliebrown.

8. “Let It Snow! Let It Snow! Let It Snow!” – Frank Sinatra

Legend has it that Sammy Cahn and Jule Styne crafted this tune in the summer of 1945 during a sweltering California heat wave; fast forward just a few years and the song is in regular rotation on every holiday station around the world.

In music, you can almost always have a winner with just three elements: a big band that really swings, a smooth chorus of backup voices, and a great crooner. We have all three meeting here in Sinatra’s “Let It Snow!”

Sinatra’s choir of voices set this song apart from what you’ll hear on modern radio – or even any version from his crooner peers. Their voices and their feature about celebrating Christmas together bring the song to a higher level – and what’s more festive and fun than getting together with friends and having a sing-a-long? Come on, now!

9. “Jingle Bell Rock” – Chubby Checker & Bobby Rydell

“Jingle Bell Rock” is a product of the 1950s, catapulting country singer Bobby Helms to his highest-ever spot on the charts. From Wayne Newton to Hall & Oates to Billy Idol, it seems like every rock artist with a Christmas album has attempted to recreate the greatness of Helms’ performance ever since.

However, just because you play rock doesn’t mean you should play jingle bell rock, guys.

The most festive and satisfying cover of the original comes from none other than two quintessential mainstays of 1950s pop radio. Collaboration among the greats is cause enough to celebrate, and what better way for them to collaborate than on a Christmas song that references sock hops and twists? Yep, there’s no better way. Chubby Checker and Bobby Rydell trading off pieces of lyrics with one another in the second go-round is purely playful, light, and merry – everything a festive Christmas song should be!

10. “Rudolph, The Red-Nosed Reindeer” – The Temptations

Here’s another hallmark of the elementary school holiday music canon that grownups might handle for memory’s sake or for when they’re gathering together at the piano for a carol sing-a-long (what, you don’t do that? You should!). Gene Autry popularized the tune (his is the best-selling version) and anyone who’s seen the stop-animation film can’t help but love Burl Ives’ voice on the song.

For purposes of festivity, however, there’s only one group that elevates the kiddie pop into the grown-up jam, and that’s The Temptations. They seriously knew how to put the fun in funk. The harmonies are top-notch, of course, but it’s the bright juxtaposition between the falsetto and the bass that really elevates the tune (I also can’t help but love the way they speak “Hey, Rudolph!” in such a commanding way. I love picturing Santa speaking to Rudolph like that). And who else can really bring soul to a song about a reindeer? Nobody else, people, nobody else.

11. “Sleigh Ride” – Leroy Anderson and His Pops Concert Orchestra

Composer Leroy Anderson gave the world “Sleigh Ride” in 1948. Like “O Tannenbaum,” the original “Sleigh Ride” did not contain any lyrics – it wasn’t until 1950 that listeners first heard The Andrews Sisters sing Mitchell Parrish’s lines about “riding down the trail, feeling comfy cozy with rosy cheeks are we.”

While artists like The Ronettes and Harry Connick, Jr. (among others) have offered their own fun and festive interpretations, Anderson’s instrumental captures the essence of an authentic sleigh ride. Horns swell and replicate the turns and hills of the landscape, temple blocks mimic the horse trots, a slapstick sounds the crack of the whip, and a trumpet whinnies like a horse at the song’s end. Instrumental onomatopoeia at its finest.

12. “Happy Holiday/The Holiday Season” – Andy Williams

What better way to conclude a holiday playlist than to wish everyone a happy holiday? This Christmas standard is another Irving Berlin masterpiece; Bing Crosby and Marjorie recorded the tune for the 1942 flick Holiday Inn.

Andy Williams’ version provides a classic crooner’s take complete with riffed lyrics, vocal scoops, and background vocalists who place a period at the end of each phrase. They offer a few fun exclamations through (“yeah!”) and Williams delivers a lively and heartfelt finale before the fadeout.

A Recipe for Instant Christmas

If you want to try your hand at putting together a festive arrangement of your favorite Christmas carol, keep these things in mind:

• Keep a moderate tempo. Think moderato to allegro (or 110-120 BPM)
• Have fun with it! From swapping lyrics to speaking certain lines or adding in extra vocalists, use an element of fun to bring more festivity to the piece.
• Look to other genres for inspiration. From Caribbean calypso to big band, what approach can you take that’s as far away from canned-strings-and-car-dealership-commercial as possible.
• Sleigh bells. When in doubt, add sleigh bells, the magical ingredient to instant Christmas goodness.

Create a simple single-instrument arrangement, or get your friends together to jam out a multi-instrumental masterpiece. Putting your personal touch on carols has the amazing effect of making you fall in love with Christmas in a whole new way.