For the fourth year in a row, my festive playlist is here. This is becoming the closest thing that Trekking with Dennis has to an annual tradition!
I absolutely love Christmas music, and I’ve been a collector of Christmas albums and songs for a long time. Every year there are new festive albums and singles, and although there are a lot of samey arrangements of a handful of “traditional holiday favourites,” there are some real gems in the mix, too. These can be new songs or simply interesting takes on classic tunes.
For me, Christmas is a holiday all about traditions and nostalgia! And Christmas music is part of that; I have very fond memories of listening to some of these Christmas songs on my father’s old record turntable before we’d even made the switch to cassette tapes! Part of what makes Christmas time feel like Christmas time is hearing some of these songs on repeat. When I used to work in a shop, I admit that sometimes I did roll my eyes when Wham! or Mariah Carey started playing on the radio for the fifth time in the space of one shift! But even then, the music was just part of what made it Christmas.
Memories are funny things, and perhaps on another occasion we’ll have to dig a bit deeper into my Christmas recollections! But for now, suffice to say that hearing some of these Christmas tunes evokes memories of going Christmas shopping after dark, with the city’s array of Christmas lights and decorations glittering on a winter’s evening.
If you missed the earlier editions of my festive playlist, you can find them here:
The videos below are all hosted on YouTube, and some may be unavailable or blocked depending on where you are in the world. However, all of the songs should be available via your streaming method of choice if you can’t listen to them here.
So let’s get started, shall we?
Track 1:
Medley: Hark! The Herald Angels Sing, O Come All Ye Faithful, The First Noel – Steve Wariner (1990)
This medley took me forever to track down! I owned a CD in the mid-1990s called something like “A Country Christmas” – which was a mix of Christmas songs by different country music artists – and this was one of the tracks. When I converted my CDs to digital I didn’t know who all of the individual artists were, so it’s been on my computer forever just under the name “Various Artists.” It was only when I decided that I wanted to add it to this year’s edition of the Christmas playlist that I belatedly learned that the singer is one Steve Wariner.
I confess that I don’t know much about Mr Wariner – other than that he has recorded several other Christmas albums! This medley, though, brings together three classic Christmas carols in a gentle country style, and the blend works incredibly well. It’s been a fixture on my festive playlists ever since I owned that CD, and I’m glad I can finally put the artist’s name to such a beautiful arrangement.
Track 2:
Christmas Dirtbag – Wheatus (2023)
Do you remember the song Teenage Dirtbag? Wheatus were a one-hit wonder with the song in the year 2000, and I remember hearing it on the radio seemingly incessantly at the time! It was a good song, though: a kind of alt-pop/pop-punk tale of teen rebellion and feeling left out at school. Well… to my utter shock, Wheatus have reworked the track with some clearly tongue-in-cheek Christmas lyrics. And every time I listen to it I get a big stupid grin on my face!
This is a song that might trigger a very specific kind of nostalgia for millennials and Gen X-ers, and you know what? I hope it makes a stir on the charts! Christmas is a time when novelty songs can often find an audience, and this thoroughly bizarre version of Teenage Dirtbag deserves all the love it can find. If you’d told me a Christmas version of Teenage Dirtbag would be in any way worth listening to I’d have laughed out loud… but then I heard it. If you aren’t convinced, just give it a listen. It only took me one go around to be absolutely hooked!
Track 3:
Step Into Christmas – Elton John (1973)
The same year that Wizzard and Slade were battling for the Christmas number one spot, Elton John also recorded and released a Christmas classic! Gosh, what a great year for Christmas songs 1973 was. Elton’s offering didn’t make much of an impression on the charts that year, though, peaking at a lowly 24th position – but it’s found a lot more love in the years since, and is now a mainstay on the radio at this time of year.
I’m a bit of an Elton fan, and this pop track is definitely up there with his other hits in terms of quality. It’s been a festive staple for as long as I can remember, really – and it wouldn’t feel like Christmas if I didn’t hear Step Into Christmas at least half a dozen times before the big day!
Track 4:
Auld Lang Syne – Dougie MacLean (1995)
I lost a close relative on New Year’s Eve 2003, and perhaps it’s for that reason that I’m not the biggest New Year’s fan. I don’t hate the holiday, but it’s one that brings up memories of that person – and of others who are no longer around. New Year is a reminder of the onward march of time, too – something that’s catching up to me! Hearing Auld Lang Syne can feel bittersweet, then, as a new year is rung in.
It’s in that spirit that I share this particular rendition of Auld Lang Syne by Scottish folk singer Dougie MacLean. I was fortunate enough to see him perform live once, and it was a truly incredible performance that remains to this day one of the best I’ve ever seen. You might know Dougie MacLean from his song Caledonia, which is often called Scotland’s “other national anthem.”
This version of Auld Lang Syne is hauntingly beautiful; a slowed-down take with traditional instruments that really encapsulates the way I feel about New Year. It might not be something you want to listen to every day – and it certainly clashes with some of the more upbeat Christmas songs on this playlist – but when I’m in the mood for it, it’s one of those pieces of music that’s emotional, nostalgic, haunting, and incredible all at the same time.
Track 5:
Stay Another Day – East 17 (1994)
Stay Another Day is one of those songs that’s become a Christmas anthem… for no other reason than it happened to be released at this time of year! Boyband East 17 leaned into the wintertime theme in the song’s music video, and a Christmas classic was born. Stay Another Day is a perfectly enjoyable ’90s pop song – and became the Christmas number one in 1994, beating All I Want For Christmas Is You by Mariah Carey in the process – but it’s not necessarily one I’d have expected to become a mainstay of Christmas playlists!
That being said… it *is* on my Christmas playlist, so East 17 clearly did something right! Stay Another Day is just one of those songs that developed an association with Christmas, and while I might’ve been surprised when it started coming back Christmas after Christmas… it’s no less Christmassy that a lot of other songs that are popular at this time of year! If you’re hearing it for the very first time, I get why it might not seem like a typical Christmas song. But for us Brits, it’s just another of our inexplicable Christmas traditions!
Track 6:
Fairytale of New York – Ed Sheeran and Anne-Marie (2017)
I included the original version of this Christmas classic on the first edition of my festive playlist back in 2020, and I can absolutely understand why people would say that Shane MacGowan and Kirsty MacColl’s vocal deliveries can’t be beaten! This version, recorded live for Radio 1 here in the UK back in 2017, is different from the original, no question. Ed Sheeran has a much softer voice than the late great Shane MacGowan – who passed away earlier this week – and that definitely changes the tone of the song. This version also makes a couple of changes to the most offensive lyrics from the original, further toning things down.
All that being said, while this cover of Fairytale of New York is certainly different… I don’t think that makes it worse. It’s just a different take on the song by two incredibly talented performers, and there should always be room for covers of even the most beloved classics! As far as I can tell, this cover version – which was performed live and never officially “released” – has never charted. But the original Fairytale of New York has returned to the top five around Christmas every year for the past few years – and in light of the recent passing of Shane MacGowan, could even be a surprise contender for this year’s number one.
Track 7:
What Christmas Means To Me – John Legend (2018)
I confess I’m not especially familiar with John Legend, but as an avid collector of Christmas albums I picked up his offering – titled A Legendary Christmas – in 2018. The album contains eight covers and a whopping six original compositions. This song is a cover of Stevie Wonder’s 1967 hit, and Wonder himself returns to play harmonica alongside John Legend, which was a nice touch!
I like the up-tempo song and jazz instrumentation, and even though I can’t remember hearing Stevie Wonder’s original version before, it’s sweet of him to join in for a collaboration on a new version of one of his hits. There are other great tracks on John Legend’s Christmas album – but this has always felt like one of the best to me, so it makes the cut on this occasion!
Track 8:
Here Comes Santa Claus – Elvis Presley (1957)
Ten years after Gene Autry wrote Here Comes Santa Claus, Elvis covered the track for his first Christmas album. Elvis’ version of the song is one that I can remember my father playing on his turntable in the run-up to Christmas; that must be one of my earliest memories of listening to Christmas music! My father had been a big fan of Elvis’ earlier albums, and may even have picked up Elvis’ Christmas Album the year it was released.
So it’s not unfair to say that there are strong nostalgic feelings and memories attached to this song in particular! But it’s a great cover version in its own right; a song well-suited to Elvis Presley’s distinctive voice. There’s also a version of this song featuring new instrumentation by the Royal Philharmonic Orchestra, recorded in 2017 as part of their album Christmas with Elvis and the Royal Philharmonic Orchestra. Though I prefer the original, that version adds a lot to the track.
Track 9:
DJ Play A Christmas Song – Cher (2023)
The second brand-new track from 2023 to make this list comes from Cher’s first-ever Christmas album. I know what you’re thinking, because I thought it too: Cher hadn’t made a Christmas album till now? That doesn’t seem right! But it’s true, and her 2023 offering – simply titled Christmas – is her first foray into the holiday music genre.
Cher is a fantastic performer, and I can already tell that this new offering is going to become a mainstay on my Christmas playlist – for as many Christmases as I have left! When DJ Play A Christmas Song reached the number-one spot on the Billboard Dance/Electronic chart in the United States, it made Cher the first performer ever to have a number one song in seven consecutive decades! The song has also charted in the UK in recent weeks – and I wouldn’t be surprised to see it rise beyond its 30th place peak as Christmas gets nearer.
Track 10:
It’s Beginning To Look A Lot Like Christmas – Maddie and Tae (2023)
In 2015, after the tongue-in-cheek Girl In A Country Song had been a big hit, it seemed as if Maddie and Tae were about to take the country music world by storm. They were even hailed in some corners as “the new Taylor Swift!” That didn’t quite happen for the duo, unfortunately, but they’re still performing and recording music together – and this year Maddie and Tae have released an extended version of their Christmas EP, containing this cover version of It’s Beginning To Look A Lot Like Christmas among other tracks.
I find this up-tempo version of the festive classic to be charming, and not too “country” if you’re not a huge fan of the genre. The duo’s vocals are a great fit for the track, and it’s always nice to get a new take on a Christmas classic. There are plenty of versions of It’s Beginning To Look A Lot Like Christmas out there – and I featured Michael Bublé’s take on it as part of the festive playlist a couple of years ago – but this version is something just a little different.
Track 11:
Ring Out, Solstice Bells – Jethro Tull (1976)
Prog rock band Jethro Tull recorded Ring Out, Solstice Bells in 1976 – and it’s become a perennial festive favourite ever since! I’m loathe to call it a “Christmas” song, because the title and lyrics are deliberately non-Christian and even pagan, celebrating the winter solstice rather than Christmas itself. But that doesn’t stop Ring Out, Solstice Bells being a great song and one that’s well worth listening to at this time of year.
This is another track that I can picture my parents listening to in one of those early Christmastime memories! I think my father must’ve owned Jethro Tull’s 1977 album Songs from the Wood, on which the track was featured after its original release. I can’t remember, though… but I know this was a song that we listened to at Christmas time! It’s another one of those strangely nostalgic songs that reminds me of those childhood Christmases.
Track 12:
Underneath the Tree – Kelly Clarkson (2013)
I still consider this track to be a “new” Christmas song… even though it’s celebrating its tenth anniversary this year! Shows how old I’m getting, eh? In 2013, American popstar Kelly Clarkson released her first Christmas album, and along with a handful of up-tempo versions of holiday classics was this original composition. It’s a great song and has been rightly hailed as a modern festive classic!
Underneath the Tree peaked at number 12 on the charts here in the UK, but was a chart-topper in the USA and Canada. I’ve seen it on multiple Christmas compilation albums and playlists in the years since, and it’s been a mainstay on my own Christmas playlist since I bought Kelly Clarkson’s album that same year.
So that’s it for another year!
I’m proud to say that, once again, we’ve managed to stay hidden from both Wham! and Mariah Carey… but as we begin to run out of top-tier festive hits, will we be able to keep that up next year? I guess you’ll have to come back in December 2024 to find out!
I hope this playlist has given you a little bit of festive inspiration, at any rate. In my admittedly foggy memories of childhood, my parents would pop on a Christmas record when we were getting the decorations out of storage in mid-December. It was great fun to dig through the boxes, finding little ornaments and pieces of tinsel that we hadn’t seen in almost a year all the while some festive songs were playing in the background. I’m sure I’m romanticising those memories; looking back with red-and-gold-tinted glasses! But memory is a funny thing, and my recollections of Christmas are a big part of why I love the holiday season so much.
I hope you’ll stay tuned, because I have a couple of other festive ideas that may (or may not, time depending) make their way to the website before the big day. All that remains to say is this: Merry Christmas!
All songs on the playlist above are the copyright of their respective record company, studio, distributor, composer, etc. All videos courtesy of YouTube. Videos are merely embedded here, and are not hosted on Trekking with Dennis. For copyright or other legal purposes, please contact YouTube directly. This article contains the thoughts and opinions of one person only and is not intended to cause any offence.
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