We’re making our lists and playing them twice.

You don’t become the best Christmas song of all time by being just another cute and fun bop, and sure enough, “Have Yourself a Merry Little Christmas” captures the dark side of the holidays; it’s a song for the cynics, the sad girlies, and the lonely boys like Dan Humphrey. Written by Hugh Martin and Ralph Blane in 1943, the song made its debut in the 1944 MGM musical Meet Me in St. Louis. In the film, Judy Garland’s character Esther and her family are gutted at the holidays upon learning that due to their father’s job, they have to move to New York City (the horror!) and thus leave their beloved home of St. Louis amid the highly anticipated 1904 World’s Fair. Esther sings the song to her 5-year-old sister, Tootie (Margaret O’Brien), and immediately afterward a distraught Tootie has an iconic temper tantrum, hitting snowmen in the yard with a big stick while scream-sobbing.

Over the decades, the association of “Have Yourself a Merry Little Christmas” with Meet Me in St. Louis fell away, and the song has become more generally synonymous with the holidays. It’s a classic for the way it stands out from the overwhelmingly positive and goofy Christmas songbook — it makes people who are lonely, be it physically or emotionally, feel seen during a season that pressures everyone to be merry and bright.

“Have Yourself a Merry Little Christmas” as we know it today has been modified from its original (and most depressing) version, which contained specific references to the feelings of the characters in Meet Me in St. Louis; subsequent renditions involved experiments with the sound, tone, and lyrics, with artists making it more upbeat, downbeat, or, in some cases, sexy. The best recordings of “Have Yourself a Merry Little Christmas” — which remains despairing across its many iterations — are filled with genuine honesty and feeling and are clearly recorded by people who can relate to the song’s themes. Christina Aguilera, Kacey Musgraves, Bright Eyes, Sam Smith, and the Backstreet Boys have all taken a crack at it, to varying degrees of success; none of their versions made this highly competitive list. Below are the ones that did.

10.

Even as an instrumental, Kenny G’s beguiling, jazzy version of “Have Yourself a Merry Little Christmas,” released in 1994, is one of the most powerful. Despite being a cover of the second-most-depressing Christmas song (behind only “Christmas Shoes”), it, like all Kenny G music, is deeply sensual in a weird yet intriguing way. Put this one on your holiday-party playlist and your guests will have Normal People sex when they get home.

9.

I hadn’t planned on including this version of the song when I began this ranking, because I didn’t know it existed. But as I thoroughly searched for the tune across many music platforms, Egg kept coming up. Did I assume music from an artist called Egg would be bad? Yes. Did their recording turn out to be one of the best, bumping many better-known renditions from this ranking? Well, here we are. In their take, which was released in 2021, Egg went back to the original lyrics from Meet Me in St. Louis. The modern, somber, alt-electronic sound mixed with the OG words honors the deeply sad spirit of the song while adding a hint of humor to it.

8.

JoJo, the singer of breakup songs such as “Leave (Get Out)” and “Too Little, Too Late,” produced when she was a teen in the aughts, released an album called December Baby in 2020. It includes her version of “Have Yourself a Merry Little Christmas,” which is upbeat and playful with a mixture of pop and R&B. JoJo’s smokey voice has become even more sensational in the years since she was a young teen who somehow harbored more bitterness toward men than Alanis Morissette and Olivia Rodrigo combined, enabling her to fully project the longing and pain required for the song.

7.

Every song from Kelly Clarkson’s 2013 Christmas album Wrapped in Red is a bells-on classic. Clarkson uses her affecting voice, one of the best the biz has seen, to imbue each moment with more feeling than the last, building to a staggering finale that can reduce even the strongest holiday-hating girlboss to a sobbing mess in the fetal position underneath the tree.

6.

Before we begin this little blurb about Coldplay’s “Have Yourself a Merry Little Christmas,” let me start by saying that I’m embarrassed about this pick and I know you’re embarrassed for me. Nevertheless, Coldplay’s simple and characteristically piano-heavy recording, released in 2001 between their first and best albums, Parachutes and A Rush of Blood to the Head, has the dark but hopeful feeling that defined their early work, a perfect match for a song that fits the same description.

5.

2017 was not that long ago, but it feels like it occurred in an alternate reality. Before she smashed a guitar on Saturday Night Live and became a bona fide rock star, Phoebe Bridgers was a minor but respected emerging musician who released a bleak recording of the bleak ”Have Yourself a Merry Little Christmas.” Bridgers’s version seems like it was recorded through tears, as if she wrote the song herself in real time.

4.

Frank Sinatra’s cheery voice has glimmers of pain and longing in his three recordings of “Have Yourself a Merry Little Christmas,” but, like all his music, it’s smooth and soothing, the audio equivalent of hugging a warm cup of coffee with shaky hands on a cold, overcast day. Sinatra is also the reason the song became a bit less downcast: Before recording it in 1957, Sinatra asked lyricist Hugh Martin to change the lyric “Until then we’ll have to muddle through somehow.” Martin obliged, introducing to the world the more optimistic phrase “Hang a shining star upon the highest bough.”

3.

Ella Fitzgerald’s recording from the 1960 album Ella Wishes You a Swingin’ Christmas proved the song could be fun. The music is jazzy and playful, with an exciting rhythm that Fitzgerald matches with her sharp, punchy voice. This version is unique in that Fitzgerald sings from the perspective of someone who has had a lonely Christmas in the past, got through it, and is looking back on the feeling with a new attitude.

2.

The best Christmas songs are the kinds that soft-rock DJ, therapist, and living legend Delilah tends to play over and over again throughout the holiday season. Amy Grant’s “Have Yourself a Merry Little Christmas” from her 1992 album Home for Christmas embodies that through and through. Grant’s polished, familiar voice shifts from sad to cheerful as the song progresses, as if she’s convincing herself while singing that she will in fact have herself a merry little Christmas. It’s dramatic as hell. There are bells.

1.

It could not go any other way. “Have Yourself a Merry Little Christmas” was tailor-made for Garland’s contralto. It’s beautiful in its simplicity. Garland doesn’t embellish the song in any way — she simply sings and lets the poignant words and rousing music speak for itself. But even this version benefitted from a lyrical reworking, as the original composition — the one recorded by Egg — was, incredibly, even more dark. Garland, along with Meet Me in St. Louis co-star Tom Drake and director Vincente Minnelli, requested a more positive second pass, and after some initial resistance the lyrics were changed. Most notably, “It may be your last / Next year we may all be living in the past” became “Let your heart be light / Next year all our troubles will be out of sight.” Sure seems like the real lesson from “Have Yourself a Merry Little Christmas” is that first drafts are always depressing.

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