These New Yorkers Made the Best Holiday Albums Ever

Few musical genres inspire as much rapid affection and hatred as holiday music. Perhaps it’s because it’s seemingly all we hear on an endless loop whenever we decide to venture out into any sort of public gathering place for one month straight. But fear not: when you step back from the madness, there’s a lot of wonderful holiday music. Maybe we’re biased, but there’s no place like New York City come holiday time. To that end, we’ve rounded up our favorite holiday albums made by New Yorkers. From classic crooners like Bing Crosby and Sinatra to more contemporary Christmas carolers like Sufjan Stevens and yes, even Dipset, these artists prove that holiday music is actually quite delightful.

Ella Fitzgerald, Ella Wishes You A Swinging Christmas
It’s a wonder how the First Lady of Jazz caterwauls her way through some classic Christmas songs (“White Christmas,” “Let It Snow! Let It Snow! Let It Snow”) on this 1960 masterpiece; on Ella Wishes You A Swinging Christmas, Fitzgerald goes so far as to reinvent many tunes in the process. The jazz icon’s loose-lipped rendition of “Jingle Bells,” which kicks off the LP, has become one of the most oft-played versions, and the entire album, cut with an orchestra conducted by Frank De Vol (of the Brady Bunch theme fame), is every bit as wild and carefree.

Mariah Carey, Merry Christmas
Merry Christmas, which has sold over 15 million copies worldwide and is the most successful Christmas album of all time, may not be Mariah Carey’s most mind-blowing album on a strictly vocal level, but you’d be hard-pressed to find one that resonated as deeply. And we all know why: lead single “All I Want For Christmas Is You” is nothing if not the quintessential Christmas song recorded in the modern era; every holiday season, like clockwork, there it is once more, steadily climbing the charts. Viewed on the whole, Carey strikes a wonderful balance on the album, delicately juggling the lighthearted feel-good nature of the release’s biggest hit with supple love songs and more elegant religious fare. We’ve included the Tonight Show with Jimmy Fallon classroom instruments version above because it’s maybe the happiest clip that’s ever been created in the history of time.

Bob Dylan, Christmas in the Heart
Whatever your feelings are regarding holiday music, if only because of sheer reputation, it’s inarguably become part of the American canon. Bob Dylan, being a historical type, recognizes this. To that end and seemingly out of nowhere, he unleashed a Christmas album upon us all back in 2009. What the musical maestro lacks in voice he more than makes up for on Christmas in the Heart via gnarly charm. His time-worn baritone is a thing of worked-over beauty on jumpy, more-obscure charmers like “Christmas Island” and can only evoke a sly smile when spread out over classics like “Have Yourself A Merry Little Christmas.”

Sufjan Stevens, Songs For Christmas
Listening to Sufjan Stevens’ 2006 Christmas offering is a delightfully manic affair: while the indie-rock superhero lathers much of the five-disc Songs For Christmas with genteel takes on standards like “O Holy Night” and “The Little Drummer Boy,” he’s just as likely to toss in some humorous originals like “That Was the Worst Christmas Ever!” and “Come on! Let’s Boogey to the Elf Dance” with equal measure. There’s no denying Stevens takes some of the typical self-seriousness out of his take on the Christmas album — and we’re all the better for it.

Frank Sinatra, A Jolly Christmas From Frank Sinatra
That effortlessly smooth voice. Those sweet, tugged-upon vowels. Sinatra may as well be the OG in terms of Christmas music, and 1957’s A Jolly Christmas From Frank Sinatra is his statement of purpose. There’s a sense of longing blended with comfort in his iconic “Have Yourself A Merry Little Christmas” while “The Christmas Song (Merry Christmas To You)” is as gentle as an early snowfall. The schmaltz factor is in full effect here, but Ol’ Blue Eyes hung his wide-brimmed hat on it and never looked back.

Bing Crosby, White Christmas
There’s just no one like him: Bing Crosby is unquestionably the Head Honcho when it comes to Christmas music. You know him from his version of “White Christmas,” which has sold over 50 million copies to date. And there he is again on 1986’s re-vamped White Christmas doing his thing on “Silver Bells” before snuggling up to the Andrews Sisters on “Jingle Bells” and “Santa Claus Is Comin’ To Town.” What Bing Crosby did to Christmas music is nothing less than completely reinvent the wheel. All we can do is thoroughly embrace it.

Louis Armstrong and Friends, The Best of Christmas Songs
If ever there was a holiday album made exclusively for staying up far too late and getting rowdy on eggnog, surely it’s Louis Armstrong and Friends’ The Best of Christmas Songs. Satchmo keeps things light and festive, spinning out horn-laden up-tempo charmers like “Christmas Night in Harlem” and “Cool Yule.” The party is fleshed out by some of the 20th-century’s greatest musical talents: Lena Horne, Dina Washington and Duke Ellington all join in on the fun.

Phil Spector, A Christmas Gift for You from Phil Spector
It takes a mighty man to create a holiday album so brilliant it transcends the genre and stands in a league of its own. That’s exactly what super producer Phil Spector did with 1963’s A Christmas Gift For You From Phil Spector. It’s all so massive and wondrous: Darlene Love laying it all on the line on “Christmas Baby, Please Come Home;” the Crystals throwing some back on “Santa Claus Is Coming To Town,” etc. Often regarded as the best Christmas album ever made, Spector’s concoction is as sprightly and engaging today as when recorded a half a century ago.

Sharon Jones & The Dap-Kings, It’s a Holiday Soul Party
It’s an undeniable challenge to freshen up holiday standards, but Sharon Jones and her wily Dap-Kings crew do just that on their recently released It’s A Holiday Soul Party. Sure, on this throwback to Phil Spector’s Christmas masterpiece, these musicians get rambunctious on “White Christmas” and even make “God Rest Ye Merry Gentleman” into a jam. But it’s the new tunes, like “8 Days (Of Hanukkah)” and “Ain’t No Chimneys in the Projects” that breath some much-needed fire into what’s become a sometimes-stale genre.

Dipset Xmas, A Dipset X-Mas
When Jim Jones and his ByrdGang music group teamed up to release this set of Christmas bangers, few could have predicted the results would be so terrifically raw. Yes, those are sleigh bells echoing in the background of A Dipset X-Mas’s opening cut, the feel-good “Dipset X-Mas Time,” and how can you not stand back in awe at Jones’ bravado when remixing his signature “We Fly High” for the holidays? Hate all you want on this hip-hop holiday get-together, but lord knows modern families need to have as much bounce in their step as possible come holiday season.