The Twelve Greatest Christmas Songs. Probably

Christmas music. You’re either one of those people who’s itching to press play the day after Thanksgiving or you’re like me, the kind of person who might scream if you hear Slade, Wizzard or Shakin’ flamin’ Stevens one more time. Chances are you’re likely have a mixture of these two camps in your abode during the festivities. The best Christmas music manages to capture the spirit of the holidays and tap into our nostalgia, making us sing along despite ourselves. To satisfy (almost) everyone, may I present Steve’s seasonal suggestions.

Whether you’re throwing a thoroughly over-the-top partay or just having family over to fight around a plastic tree, a typically topical playlist is essential to set the mood. Even if you’re just trying to get hyped for the holidays these twelve tunes will do the trick. These are not only a delicious dozen* of the greatest Christmas songs of all time, but also some of the most enduring. From old-yule classics to modern-day covers, for you to enjoy over the festive season. Let’s hope it’s a good one.

Have Yourself a Merry Little Christmas (1944)

Judy Garland’s death four days before I was born indirectly sparked New York’s famous Stonewall Riots that kickstarted gay rights movements across the world. And if any tune reflects the anxious uncertainty with which we greet 2019, it’s this 75-year-old bittersweet chestnut.

The song was introduced by Garland in Vincente Minnelli’s movie musical Meet Me in St. Louis, a picture about four daughters coming of age while getting ready to move to the Big Apple. It’s doomy melancholic quality brilliantly captures the nostalgia and homesickness so many people feel around this time of year. In fact, when Frank covered the song he had the lyrics rewritten, so bleak he did find them.

Bonus: the sound of Judy singing just about anything seems to instantly alleviate stress brought on by a house full of relatives. Her daughter once made an album with the Pet Shop Boys, you know.

Santa Baby (1953)

Something about this cheeky tune just makes me want to throw on a colour coordinated romper suit and throw down a few synchronized spins. This corny classic is all about an impatient Eartha Kitt expecting some pretty extravagant Christmas gifts, and even though this tale of fireside seduction is a holiday recording, it’s one of the future Catwoman’s most well-known songs.

The slag Madonna covered it in 1987, thinking she was Betty Boop, all hiccuping flirtation and winking vamps, but there’s nothing like a good Eartha.

The Christmas Song (1961)

Everyone knows this seasonal staple as the one where the great Nat ‘King’ Cole sings about “chestnuts roasting on an open fire.” Cole recorded severe versions but the Sixties take is the most played.

Frank Sinatra, no stranger to Christmas recordings, also had a creditable stab at it, and in 1995 a ‘digital duet’ was created from the two renditions. For many though, the Nat version is the definitive one. It’s so popular that it was inducted into the Grammy Hall of Fame in 1974.

Christmas (Baby Please Come Home) (1963)

Through the ’60s, Phil Spector was focused on singles, with his definition of an album being “two hits and ten pieces of junk.” He took a different approach, however, when putting together a Christmas album in 1963, where the producer extraordinaire put his rousing Wall of Sound to good use. The key track and only original song on the album was Christmas (Baby Please Come Home), which he wrote with Jeff Barry and Ellie Greenwich and gave to his favourite backing singer to record.. 

Darlene Love pulls out a belter on one of the all-time killer Christmas anthems, pleading for the return of an absent lover as the cacophonous wall comes down like an avalanche. It had the ill-fortune of arriving in record stores on the exact day that US president John F. Kennedy was assassinated. Holiday mood dampened, both single and album were withdrawn and unavailable for years, though they went on to become cult classics in every way. It’s been covered by everyone from U2 to Mariah Carey to Cher (who’d sung back-ups on the original), but nobody can match Love’s emotion and sheer vocal power.

River (1971)

It’s important for us to acknowledge here the inherent sadness that the holiday period can inflict upon the best of us. In those times, your most empathetic ear comes in the form of Joni Mitchell’s River – it’s a poignant, turbulent and kinda beautiful nod to the starkness, and the solemnity of Christmas.

Right from the opening piano chords (Jingle Bells gone bittersweet) you know this is going to be a seasonal song with a difference. ’Tis the season, but Joni’s feeling blue, very Blue: she’s lost her baby (maybe Graham Nash) and all she wants to do is skate away, but that’s not easy when you’re spending the holidays in sunny California. It’s as painful and pitiful as anything she ever recorded. Happy Christmas? Oh, Hi John…


Happy Xmas (War Is Over) (1971)

In 1969, John Lennon married Yoko Ono, and he quit The Beatles. Two years later, husband and second wife teamed up with the Harlem Community Choir to record this seasonal stalwart. Though a dispute between John and the Fab Four’s British publishing company, Northern Songs, delayed the song to the extent that it had to wait until Holiday ’72 to come out in his home country.

Euphoric and scathing, as hopeful as it is resigned, this definitive festive peace-on-earth statement has transcended its original anti-Vietnam War protest purpose to become a classic Christmas hit (twice over), and, incidentally, Neil Tennant’s favourite Yuletide 45. More on him later.

Peace On Earth/Little Drummer Boy (1977)

White Christmas, Bing Crosby’s classic hit about a picturesque snowy scene, is one of the most famous Crimbo songs ever — Guinness World Records even named it the best-selling single of all time. It was on this basis that David Bowie incongruously agreed to duet with the Old Groaner on his 1977 special Bing Crosby’s Merrie Olde Christmas. This surreal encounter between the Thin White Dame and the good ol’ boy of American family TV has become the stuff of legend. After the Dame ‘mistakes’ Bing for a butler and Crosby jibes at Bowie’s music taste, they launch into a medley that was a shotgun marriage of two songs: something old, something new.

Although Bowie explained in the song’s scripted preamble that Little Drummer Boy was the favourite of six-year-old Zowie (later Duncan) Bowie, the 30-year-old father despised it: “David came in and said: ‘I hate this song. Is there something else I could sing?’” Ian Fraser, one of show’s musical writers, said. “We didn’t know quite what to do. When we told Bowie about the number, he said, ‘I won’t sing that song. And if I have to do that song, I can’t do the show.’”

Fraser and Larry Grossman, another of the show’s writers, hatched a plan. “We decided the best way to salvage the arrangement was to do a counter-melody that would fit in within the spaces, and maybe write a new bridge, and see if we could sell him on that. It all happened rather rapidly: I would say within an hour we had written it and were able to present it to him again.”

Crosby and Bowie rehearsed for less than an hour before Little Drummer Boy was recorded. “They sat at the piano and David was a little nervous,” Mary Crosby remembered. “Dad realised that David was this amazing musician, and David realised that Dad was an amazing musician. You could see them both collectively relax, and then magic was made.”

After the recording, Crosby would call Bowie a “clean-cut kid and a real fine asset to the show”. “He sings a lovely counterpoint,” he added, “has a great voice, and reads lines well”. The results are… astounding. Sadly, Bing went bong on a golf course in Madrid a month later, and in 1982, just as he was prepping Let’s Dance, the recording was belatedly issued by Bowie’s former record label as a single, much to the singer’s chagrin. 

Christmas Wrapping (1981)

Chance meetings with cute guys in the supermarket are the stuff Yuletide fairytales are made of, especially when they’re set to bubbly, sax-powered New Wave. And if you love New York bands like Blondie and Talking Heads, this fizzing, funky dance-around-the-tree hipster fave is surely the Christmas song for you.

It begins cynically with singer Patty Donahue declaring insouciantly “I think I’ll miss this one this year”, before an unexpected romance blossoms in the closing stages and warms her jaded cockles. As festive tunes go, this one’s as dry and delicious as champagne paid for by your boss.

2000 Miles (1983)

It sounds like a swoonsome take on the classic ‘it’s Christmas, I miss you’ long distance lovers theme, but the Pretenders’ beautifully icy ballad gets much sadder when you realise Chrissie Hynde wrote it for the band’s original guitarist James Honeyman-Scott, who had died the previous year.

Honeyman-Scott’s replacement was Robbie McIntosh, who pays tribute with some gorgeous arpeggios: the closest a guitar gets to the sound of snowfall. If I had to pick a favourite I’d probably plump for this, though I had to include the next one for personal reasons, obviously.

Last Christmas (1984)

A slushy ballad of doomed romance, and one ever more poignant due to its author’s tragic death two years ago today. Then a mere slip of a 21 year-old, George Michael wrote, produced, performed and painstakingly played every single instrument on the track. Having gradually rid the recording process of interfering producers, managers, record company executives and even his Wham! bandmate Andrew Ridgeley, the only people admitted into the studio were engineer Chris Porter, and two assistants – not that they had much input. Porter remembers “desperately wanting to play sleigh bells”, but like everything else, they were jangled only by Michael himself.

Last Christmas features simple snowy synths, a Roland drum machine, and a video that boasts some truly memorable/appalling knitwear. But what really sets the song apart is George Michael’s heart-on-sleeve delivery: his genuine heartbreak horror (“My God! I thought you were someone to rely on”) and wistful, sultry whispers. The words ‘Merry Christmas’ never sounded so sexy. Kept off of the festive No.1 by Band Aid’s mammoth Do They Know It’s Christmas (which George sang on), this record has the distinction of being Britain’s biggest selling song that failed to reach pole position. 

Bonus: what was knocked off the top spot when Wham! and Band Aid bludgeoned their way into the chats that second week of December 1984? ‘Twas Frankie Goes To Hollywood’s The Power Of Love, which very nearly made my personal countdown today, alas it failed at the final hurdle when I realised it doesn’t mention either a) Christmas b) Sleigh bells or c) Santa. Sorry Paul!

Winter Wonderland (1987)

The lyrics to the charming Winter Wonderland are about a couple enjoying a picturesque winter landscape. They build a snowman, who they agree to pretend is Parson Brown. They imagine the snowman asking if the couple is married, to which they tell him that they are not and tell the snowman that he can marry them. It’s a synch. Few did the song as well as the delightful, swinging take from the First Lady of Jazz, Ella Fitzgerald though Dean Martin‘s Sixties take is also upbeat and fun to listen to.

But in ’87 Dave Stewart and Annie Lennox, in the middle of Eurythmics‘ synthtastic Savage period, dashed off a brilliantly chilly electro reading for the first of the A Very Special Christmas charity albums, which aided the Special Olympics. Whatever the version, Winter Wonderland’s a necessary addition for every festive dinner’s playlist.

It Doesn’t Often Snow At Christmas (1997/2009)

Originally released as a fan club freebie, Pet Shop Boys‘ off-beat offering captures the mix of ambivalence and warmth that Christmas can somehow conjure up pretty perfectly: a sweetly sardonic dance banger which appears to take some of its lyrical inspiration from Kate Bush’s December Will Be Magic Again** by name-checking Bing Crosby, as well as “this year’s festive number one.”

Of course, ten years earlier, Tennant and Lowe’s souped-up synth reimagining of the country folkie Always On My Mind caused a major chart upset by depriving Rick Astley and those smelly old Pogues from the top spot. IDOSAC happens to be Elton John‘s favourite Christmas song and was finally given a full release on the duo’s Christmas EP in 2009, giving Team PSB their, appropriately enough, 45th singular showing in the UK Top 40 to date, though that figure rises well into the fifties if you include their work with Dusty Springfield, Eighth Wonder, David Bowie Robbie Williams and Liza Minnelli. She’s Judy Garland’s daughter, you know.

Snow in Sun (2012)

Whether she’s covering Pet Shop Boys, Kate Bush or being the vocal half of that sadly-on-hiatus jazz pop duo, there is something about the wonderfully melancholy quality in Tracey Thorn‘s voice that would seem to make the idea of a Christmas album by her improbable. But Tinsel and Lights is no ordinary festive set. It is as singular in its choice of material as the Everything But The Girl’s voice is. Produced by Ewan Pearson, it’s a record that works on its own merits rather than being a cynical cash-grab. Thorn shows impeccable taste when it comes to picking covers. Not always settling for the obvious or clichéd, there are only two standards, in Have Yourself a Merry Little Christmas and River, both featured earlier in this article.

For the purposes of balance the rest is compiled from material written by more contemporary composers: Stephen Merrit, Low, Sufjan Stevens and Jack White among them. And this, the Green Gartside-scribed Snow in Sun, originally tucked away on Scritti Politti’s 2006 album White Bread Black Beer

Snow in Sun glistens with laid-back pop twinkle, and while it is a classy meditation on Christmas, it makes no attempt to manipulate the listener’s feelings. Instead, with its sheer musical quality, and the depth of tenderness and empathy in Thorn‘s voice, it highlights the season’s complexities in the face of everyday life. And the album from which its extracted swiftly became my favourite Christmas album ever. Clever.

Have a cool yule.

Steve Pafford

* Yes, yes, I know it’s 13. My dozen came straight from the baker. Lovely buns too. 

**Kate Bush‘s aforementioned one-off single isn’t without merit, and is, as they say, bubbling under…

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