For the past 20 years, I’ve been reviewing every new Christmas album and accumulating a best of year playlist. I have literally reviewed hundreds of albums and ordained over 200 songs as worthy of Christmas party play over the year. At my 20th Anniversary, I’m looking at every CD I’ve ever pulled a song from and saluting the best 10 of the generation. Some of them are landmark. Some of them may surprise you.
1. A Very Special Christmas vol. 1 & 2 1987; 1992


Although two separate albums in a franchise that went on far too long, reducing itself into pointlessness, these two are so superior that they complement each other and function as a perfect two CD set. Once the territory of Time Life and a bunch of deceased crooners and your parents’ favorite recording stars who gave us all the holiday music we know and love, these initial offerings changed the game for Christmas music and redefined it’s boundaries. So far ahead of its time, producer Bob Geldoff assembled the biggest names in pop music to reinvent the classics in their contemporary styles and the results were off the top 40 chart. Between the two, we were treated to now classic standards like the Pointer Sisters’ festive “Santa Claus is Coming to Town”, Annie Lenox’s enigmatic “Winter Wonderland”, John Cougar Mellenkamp’s rockabilly “I Saw Mommy Kissing Santa Claus”, Madonna’s bimbo-esque “Santa Baby”, and Whitney Houston’s soaring “Do You Hear What I Hear?” that all still get radio airplay.
2. Cher Christmas 2023

Just when it seemed that Christmas music had peaked and no one had anything new to offer, leave it to the legend herself to for the hundredth time in her career to change the game once more. And not just because I’m a lifelong fan, this album does everything I’ve used as criteria right: the song balance, the flawless arrangements, the artist’s personality, the iconic collaborators (even upgrading their own songs here). Cher never ceases to amaze me. And it just does my heart good to objectively find an album that knocks your other girl to #3. I honestly spent 2 days playing them back to back and can honestly say that Cher’s album is superior, even taking Carey’s importance as introducing the pop artist as holiday artist at the top of their prime. Congratulations Cher, and thank you for settling the love/hate dichotomy below.
3.Mariah Carey Merry Christmas 1994

Everybody pick yourselves up off the floor. Once upon a time, children, believe it or not, their lived a pop princess named Mariah who wasn’t batshit crazy. Or at least had a manager/husband who had the good grace to keep it all effectively hidden from us. She was actually relevant to contemporary music and well respected in the industry, not a self-absorbed walking catastrophe waiting to happen. Personally, even then I always felt she was given more credit than she was due. Everyone praised her belting voice. All I heard was a hundred person backup choir covering for her. Everyone marveled at her self-proclaimed 8 octave range. All I heard was bird chirps, smoke alarm beeps, and notes only dogs could hear. Everyone said she was a super hot international beauty. I saw a Long Island Lolita who couldn’t keep her clothes on. I have always had a love/hate relationship with this album because I personally despise her as a pretentious, shallow, barely-talented attention whore who thought the world owed her everything. That’s how good this CD is. Love her or hate her (hate her), this CD rocked to the top of the charts as the best selling solo Christmas album of all time when the genre was relegated to your parents’ favorite antique acts and dead crooners. The first of it’s solo kind, she took the Very Special concept and showed that a contemporary artist could reinvent the formula and place Christmas music back on the pop charts. She scored big with carols like “Joy to the World” (extra points for incorporating the infamous Three Dog Night “Jeremiah was a bullfrog” lyrics) and contemporary classics like Darlene Love’s “Christmas (Baby Please Come Home)” (truthfully the best version since Miss Love until Leona Lewis rocked her off that pedestal in 2013). She even delivered the most successful permanent addition to the new pop Christmas cannon since, the now ubiquitous “All I Want For Christmas Is You”, legitimately a post modern classic in its own right. I still maintain the success was less hers and more producer/husband Tommy Matolla’s for once again hiring the big 100 person gospel choir to back her up/sing over her and the best arrangers in the industry to drown her out (and keeping her Santa outfit modestly covering everything), but it’s a success nonetheless. However, in 2010 I received vindication for my loathing when she followed this landmark megahit up with the laughably dreadful 2010 vanity sequel Merry Christmas II U (the pretentious faux ghetto title alone….ugh), and the now legendary dueling live debacles at Rockefeller Center 2015 and New Years Eve 2016, and Mariah’s reputation is rectified where it belongs—on the bottom of the trash heap of pop music past. But yes, despite my negative feelings I harbor for her, I recognize that she pioneered the way for every superior Christmas CD to follow so have to give her credit for the courage and foresight to pave the way. I know, close your shocked, gaping mouths and read on.
4. Hanson Snowed In 1997

Don’t laugh. The Brothers Hanson are not, despite public perception, your typical teeny-bopper boy band. At the top of their MMMBop days, they put together one of the best contemporary Christmas albums ever. Youthful rock and roll spins on some of the best contemporary versions of everything from “What Christmas Means to Me” to “Rockin’ Around the Christmas Tree” to “Christmas (Baby Please Come Home)”. Plus they played their own accompaniment and freely passed the lead vocals around. Hanson is truly one of the most underrated (and the only actual) boy band acts around solely because they made “MMMBop” look too easy and got too successful, which eclipsed their natural talents. To prove their point, they are the only act to win the best CD award twice, with this initial release and their long awaited 2017 follow-up, Finally It’s Christmas, even if their win for this was grandfathered in.
5. Leona Lewis Christmas with Love 2013

Lewis dropped a highly anticipated CD that was pretty much a solid salute to the immortal Darlene Love and the Phil Spector Wall of Sound, which is ideal for Christmas music, and it’s terrific. Arguably the best versions of “Christmas (Baby Please Come Home” and “I Wish It Could Be Christmas Every Day” every recorded since Miss Love and The Wizzards released the originals. Minus a breakout hit, (which should have easily been One More Sleep, but radio stations seem to only allow one new hit a year, and she was competing with American star Kelly Clarkson who won that duel) this album seriously rivals Carey’s classic for the best female pop vocalist Christmas CD ever. Carey just ranks above for doing it first when no one else was. And of course the landmark breakout song that is still everywhere.
6. Josh Groban Nöel

When it comes to formal Christmas, there is no one like Groban’s smooth, warm baritone to deliver all the classic carols. Unlike most others on the list, his hymns are his strong point. “O Holy Night” is definitive, “Ave Maria” is legit, and when he uses a backup gospel choir, it’s the Mormon Tabernacle. Take that Mariah.
7. Kelly Clarkson Wrapped in Red 2013

Clarkson’s debut in the field was a narrow second to Leona Lewis that year, but it’s nonetheless an incredibly strong album, even producing a bona fide contemporary hit in “Underneath the Tree”. A great blend of standards and original tracks, this album shows how well Clarkson understands both pop music and her position in it. I maintain she’s one of the smartest and most business savvy pop stars around today
8. Michael Bublé Christmas 2011

The charming Canadian crooner turned out an album so good and so defining of his style that they let him rerun the same Christmas TV special every year since. Bublé’s smooth voice is the modern-day seasonal equivalent of Bing Crosby or Andy Williams, and a natural blend for holiday classics. He’s as comfortable with pop songs like “Christmas (Baby Please Come Home)” as he is with standards and hymns and this CD is an easy listening favorite across the board
9. Rockapella Christmas 2000

Before Pentatonix or The Sing Off, the granddad of all modern á capella groups is the 5 man Rockapella, the epitome of the genre before it was a genre. Today, they are most famous to one generation for singing the theme song to Where in the World is Carmen Sandiego?, and to the generation before them as the spokes singers for a classic series of Folgers’ Coffee commercials. But in their heyday they were the best of the best and you can hear it all here with this amazing collection of work, with highlights like a Carmen Sandiego/smooth criminal rendition of “You’re a Mean One, Mr. Grinch”, and the only arrangement on record in the history of the Review and Playlist to actually combine standard “It’s Beginning To Look a Lot Like Christmas” with the counter melody that Meredith Willson wrote for it, “Pine Cones & Holly Berries”. Even if they do throw an odd third melody in a Rudolph-themed version of “Glow Worm” into the mix, it fills the void. If there’s ever a cool vocal trick you’ve head Pentatonix pull off, Rockapella did it first 30 years ago.
10. Levi Kreis: Home for the Holidays

The Tony winning (as Jerry Lee Lewis in Million Dollar Quarter) Tennessee native musician and recording artist shows off all those qualities in this fun, upbeat CD with jazzy to gospel influences of a great variety of standards. He’s at his best when able to show off his mad piano skills like his slam-the-piano-against-the-wall arrangement of “You’re a Mean One, Mr. Grinch”, but he’s also effective in tickling quieter ivory on selections like “Hard Candy Christmas”, Joni Mitchell’s “River”, and Brenda Lee’s “Christmas is Just Another Lonely Day”. Most importantly, you can hear the fun and Christmas cheer in over note he and his band play. Trust me, Kreis is the best artist you’ve never heard of (unless you faithfully follow my annual Christmas CD review, in which case you’d know he won in 2018.)
The Best CD of Every Year of the Christmas Playlist
Honorary Pre-Playlist winners:
1987 A Very Special Christmas
1992 A Very Special Christmas, vol. 2
1994 Mariah Carey, Merry Christmas
1997 Hanson, Snowed in
2000 Rockapella: Christmas
Winners:
2001 Barbra Streisand: Classic Memories
2002 Hillary Duff: Santa Claus Lane
2003 Whitney Houston: One Wish
2004 Jessica Simpson: Rejoyce
2005 MercyMe: The Christmas Sessios
2006 Bette Midler, Cool Yule
2007 Josh Groban: Nöel
2008 Harry Connick Jr.: What a Night!
2009 David Archuleta: Christmas From the Heart
2010 Glee: The Christmas Album vol 1
2011 Michael Buble: Christmas
2012 CeeLo Greene: Cee Lo’s Magical Christmas
2013 Leona Lewis: Christmas, With Love
2014 Idina Menzel: Holiday Wishes
2015 Pentatonix: That’s Christmas To Me (Deluxe Edition) */ MercyMe: It’s Christmas
2016 Home Free: Full of (Even More) Cheer */ Brett Eldridge: Glow
2017 Hanson: Finally It’s Christmas
2018 Levi Kreis: Home for the Holidays
2019 John Legend: A Legendary Chrstmas (Deluxe Edition)*/ Lea Michele: Christmas in the City
2020 Dolly Parton: A Holly Dolly Christmas
2021: Kelly Clarkson: When Christmas Comes Around…
2022: Girl Named Tom: One More Christmas
2023: Cher: Christmas
*In seasons where an expanded Deluxe version of a previously released album wins, a co-winner was also selected from new entries.