A Festive Playlist To Get You In The Holiday Spirit!

Welcome to the sixth edition of my festive playlist! This is an annual tradition here at Trekking with Dennis, as I love to jump-start the holiday season by sharing a few of my favourite Christmas tracks.

I’ve been a collector of Christmas music and albums for… well, too long, let’s just say! I started my collection with cassettes and CDs, I made my own mixtapes of my favourite festive songs, and in recent years I’ve gone digital with MP3s and FLAC! I love uncovering new Christmas albums, either by artists I’m familiar with or by people I’ve never even heard of. There are so many great Christmas songs out there, be they new takes on classic tracks or brand-new compositions. Every year, I go through the charts and lists of new releases, trying out new Christmas albums and songs… and adding to my ever-growing festive playlist!

Photo of a house adorned with many Christmas lights and ornaments.
There’s a house like this in every town, right?

As I’ve done for the past few years, I want to share a few of these tracks with you today. And if you missed them in years gone by, be sure to check out the earlier editions of my festive playlist. Pick your favourite songs, or just add them all together and you’ll be all set for your Christmas party! Here’s last year’s edition, click or tap here to listen to 2023’s edition, here comes the 2022 edition, and the 2021 edition, and finally, the first edition from 2020. Right! Let’s get the important bits out of the way then we can listen to some songs!

All of the songs below are embedded via YouTube. However, if one or more won’t play for you in your part of the world, check other streaming platforms, as I daresay *most* of these songs will be accessible somehow. And if you feel like I’ve missed one of the big festive hits, check out those earlier editions of this playlist, because I may have already covered them in the past. Finally, if you hate all of the songs I’ve chosen… *that’s okay!* There are plenty of wonderful Christmas songs in all kinds of genres to enjoy at this time of year, and we won’t always agree on which ones are the best. I share my selections with you in the spirit of the season.

Stock photo of a little girl lying down under a Christmas tree.
Have you put up your Christmas tree yet?

For the last five years, we’ve managed to dodge both Wham! and Mariah Carey. But… can we keep that up indefinitely? Or have the (jingle) bells finally begun to toll for us? Scroll down to find out!

Underneath each embedded video, I’ve written a couple of paragraphs about each song, sharing my thoughts, how I encountered them, their recording histories, and such like. I hope this playlist will be a bit of festive fun now that December has arrived.

Without any further ado, let’s fire up the gramophone and listen to some Christmas songs!

Track #1:
It’s the Most Wonderful Time of the Year – Andy Williams (1963)

Let’s start with a bona fide Christmas classic this year! Andy Williams was a hugely popular American entertainer, both as a singer and as the host of his self-titled TV show, and he recorded this track for his first Christmas album in 1963. It wasn’t released as a single back then, but The Andy Williams Christmas Album topped the charts that year (and for two years afterwards, too) and was certified gold in the United States in 1964.

It’s the Most Wonderful Time of the Year has, in recent years, been a mainstay on the singles chart thanks to digital downloads and streaming. A CD single was issued in the UK in 2007, after the song picked up traction, and it hasn’t dropped out of the charts at Christmas time since then. It’s a wonderful trad-pop song of the kind that Williams was known for, and I can see why it became an instant Christmas classic! It’s the Most Wonderful Time of the Year has also spawned many cover versions, including recordings by Amy Grant, Johnny Mathis, and even Kylie Minogue.

Track #2:
Wonderful Christmastime – Christina Perri (2023)

We covered Paul McCartney’s original festive hit Wonderful Christmastime on an earlier edition of this playlist, but pop/rock singer Christina Perri put a totally unique spin on the track. And I happen to really like it! Perri’s version is shorter, clocking in at just under two minutes as opposed to the original’s three-and-a-half, which is an interesting choice – but the song doesn’t feel like it’s missing anything. The slowed tempo and simple instrumentation also give the song a gentler, almost haunting feel, emphasising the beauty of the lyrics and composition.

Christina Perri’s album Songs for Christmas was released in 2023, and as far as I can tell it didn’t chart. So this cover version seems to have flown under the radar, because I don’t think it was released as a single. But if you missed this new take on Wonderful Christmastime… give it a try. I really think it’s something special.

Track #3:
Wonderful Dream (Holidays Are Coming) – Melanie Thornton (2001)

Chances are, you know this song already – or at least a version of it! Wonderful Dream (Holidays Are Coming) is the Coca-Cola Christmas advert song, though that version is shorter and has some altered lyrics. This version of the song is longer, and while it isn’t *explicitly* about Christmas, the association is there and I’ve had it on my festive playlist for years as a result! The longer version of the song doesn’t mention Coke, so this isn’t just an overblown jingle; it’s a beautiful song well worth listening to in its own right.

The story surrounding Wonderful Dream (Holidays Are Coming) is actually rather sad. Melanie Thornton passed away just days before the song’s release, having only recorded one solo album after leaving the group La Bouche a year or so earlier. The song proved to be a hit in Germany, Austria, and Switzerland, coming close to topping the charts in all three countries in 2001. It also regularly returns to the charts in those countries at this time of year, thanks to digital downloads and streaming – and was eventually certified platinum in Germany.

Track #4:
Rudolph the Red-Nosed Reindeer – John Denver (1975)

Honestly, we could make an entire John Denver Christmas playlist! The country-folk singer recorded plenty of Christmas songs during his career, but I’m choosing this version of Rudolph the Red-Nosed Reindeer this year. Don’t confuse the 1975 recording for his later 1990 recording of the same track, as they’re quite different! Both are good, but they’re quite different in tone and instrumentation.

Despite being released at what was arguably the pinnacle of his fame, John Denver’s first Christmas album – 1975’s Rocky Mountain Christmas – didn’t storm the charts. This version of Rudolph wasn’t released as a single, either. There was a TV special hosted by John Denver in 1975, also called Rocky Mountain Christmas, though, and from what I can tell it was well-received by viewers at the time. In any case, I enjoy this version of a festive classic!

Track #5:
Love This Christmas – Rick Astley (2020)

’80s pop star – and original internet meme – Rick Astley returned in 2020 with an unexpected Christmas song! And you know what? It was pretty darn good. The song has the feel of festive hits from years gone by, reminding me a little of songs like I Wish It Could Be Christmas Everyday. Backed up by a video that also leans into that style… I really enjoyed what Rick Astley created, and the song has been on my festive playlist for the last five Christmases already!

However, Love This Christmas didn’t make a splash on the charts, failing to graze even the lower reaches of the charts in the UK or anywhere else! A bit of a shame, but perhaps not totally unexpected for an artist who might not unfairly be called a “one-hit wonder” nowadays. Still, Love This Christmas is, in my humble opinion, a modern-day festive classic, and well worth listening to if you missed it back in 2020. And given everything that happened that year… I wouldn’t blame you if you were a bit busy!

Track #6:
My Favourite Time of Year – The Florin Street Band (2010)

I agree with The Florin Street Band: Christmas really *is* my favourite time of year! And this song really encapsulates that feeling; a gentle love letter to the festive season and all it brings. It’s got a British edge to it, too, with references to carol singing, and the video leans into a Victorian Christmastime aesthetic that reminds me of A Christmas Carol. It’s a beautiful song, but the video also adds a lot, making My Favourite Time of Year a real multi-sensory experience!

The Florin Street Band was put together to make My Favourite Time of Year, as the creator wanted to bring back some “Christmas magic” to the music scene. The song didn’t chart, but it has raised money for charity, been covered by school choirs and bands across the UK, and even headlined ITV’s “Text Santa” appeal a few years ago. The Florin Street Band is back, though, in 2025, with a new song and video scheduled to premiere later this month.

Track #7:
Merry & Happy – TWICE (2017)

2025 has been the year of K-pop for me! Well, not really – but I did enjoy the film KPop Demon Hunters, which features music by Korean girl group TWICE. That sent me down a rabbit hole of listening to some of their other music – including this Christmassy number from 2017! I can’t understand the lyrics, of course… but I like it. It’s a cute, upbeat Christmas song, with some jingling bells in the chorus… and that’s all I need, really!

I confess that I know very little about TWICE. But I can tell you that Merry & Happy was an addition to their first album when it was re-issued in 2017, and it charted in Korea, Japan, and on the Billboard World chart in the United States. I wouldn’t have come to listen to it but for KPop Demon Hunters, but I’m glad I did – and it will join my festive playlist from here on out!

Track #8:
So Near To Christmas – Alvin Stardust (1984)

I am unashamedly an Alvin Stardust fan! My Coo Ca Choo and Jealous Mind are just perfect ’70s glam rock songs, in my opinion. And yeah, hearing them on my dad’s old record player when I was a kid is probably the reason why I think so! In 1984, though, after the peak of his career, Alvin Stardust came back with this beautiful slow-paced Christmas track. It reminds me a little of Mud’s Lonely This Christmas, which we talked about on an earlier edition of the playlist.

So Near To Christmas peaked at number 29 on the UK charts in 1984, and did a bit better in Ireland, where it reached a creditable place at number 15. It would be Alvin Stardust’s last notable single, as subsequent releases didn’t chart. In the ’90s, Alvin Stardust had a recurring role on Hollyoaks, a British soap opera, and continued touring and performing on TV through the 2000s and into the 2010s.

Track #9:
The First Noel – Mark and Maggie O’Connor (2025)

Representing the country music genre, we have married couple Mark and Maggie O’Connor, with their version of the traditional carol The First Noel. Their album, A Christmas Duo, was released not long ago, and contained this really beautiful take on one of my favourite carols. Using only fiddle and guitar, and with Maggie O’Connor taking the lead vocal part, this new version has the feel of something much older… almost timeless.

Mark O’Connor has won three Grammys in a long career, and I think I’m right in saying that this isn’t his first Christmas album – though it is his first as a duet. A Christmas Duo hasn’t charted yet, but at least one track (The Holly and the Ivy) has been picking up some attention. Sometimes, what I need is a gentle, classic take on a traditional carol – and that’s exactly what this version of The First Noel delivers.

Track #10:
Another Bloomin’ Christmas – Mel Smith (1991)

A couple of years ago, I wrote about the animated Christmas special Father Christmas, which aired here in the UK in 1991. I can vividly remember watching it on Channel 4 that year, and it’s been a part of my personal festive celebrations ever since! Included in the special was this song, sung by comedian Mel Smith in his guise as this version of Father Christmas – a.k.a. Santa Claus! And it’s a lot of fun. I definitely encourage you to watch the special if you haven’t seen it already, as it adds a lot of context for the song, and you can read my full thoughts on Father Christmas by clicking or tapping here.

The song was released as a standalone single in 1991, with cassette, vinyl, and even CD versions being made available. Despite the popularity of the TV special, however, it only peaked at a lowly 59th position that year. Mel Smith’s other festive hit – a cover of Rockin’ Around the Christmas Tree, which was a collaboration with singer Kim Wilde – had landed at a much more respectable third place a few years earlier! For more on that track, see last year’s edition of the festive playlist.

Track #11:
Little Drummer Boy – The Baseballs (2012)

I had the incredibly good fortune to see The Baseballs play live once, and the German rock ‘n’ roll group is one of the few acts I’ve seen live who sound basically no different to their studio recordings. I think I included their cover of Rockin’ Around The Christmas Tree on an earlier edition of my festive playlist, but this year I’m choosing their upbeat, rock ‘n’ roll take on Little Drummer Boy – because it’s just great fun!

The Baseballs always struck me as a unique act, with their musical style and even their clothes harkening back to the dawn of rock ‘n’ roll in the 1950s. I’ve collected most of their albums at this stage, most of which contain cover versions of more modern tracks, reimagined in that old school rock ‘n’ roll style. This version of Little Drummer Boy wasn’t released as a single so didn’t chart independently, but the album it’s taken from – Good Ol’ Christmas – did reasonably well in Germany, Austria, and Scandinavia back in 2012.

Track #12:
I Love Christmastime – The Gleeman (2022)

I confess that I don’t know very much about The Gleeman, but his festive song I Love Christmastime is a beautiful celebration of this time of year. 2022 was The Gleeman’s debut, with his first album dropping earlier in the year before this festive release. It’s another track that feels timeless, like it could’ve been recorded years ago and been part of our celebrations for a long time. I like the composition, the choice of instruments, and the gentle, celebratory lyrics.

I Love Christmastime was reissued in 2023 as a charity single in support of War Child, and was tipped as a potential Christmas number one that year. I’m sure the song raised a lot of money for charity, and it seems to have been downloaded quite a few times on iTunes, but it didn’t make it to the official UK charts that year. Still, it’s a great festive track, and one I’ve really come to enjoy.

So that’s it… till Christmas 2026!

Vintage photo of a snowy, Christmassy scene in Norway.
A very Christmassy scene!

I hope this has been an enjoyable playlist. If I’ve helped even one person find one new Christmas song that they’ll enjoy at this time of year, I reckon I’ve done a good job! And in any case, it’s always a lot of fun to dig through my playlist and find more festive favourites to talk about. It’s a nice way to jump-start the festive season now that we’re into December.

And hey, would you look at that? We’ve managed to hide from both Mariah Carey and Wham! for the sixth year in a row. But surely, *surely*, we’re running out of holiday hits by now… right? You’ll have to join me next year to see if we can keep the streak going!

Stock photo of a model Christmas village.
Such a cute Christmas village!

I have a few more Christmassy ideas which may (or may not, time depending) make their way onto the website before the big day. And later in the month, I hope you’ll join me for my annual End-of-Year Awards, in which I’ll hand out some imaginary trophies and statuettes to some of my favourite entertainment experiences of 2025. But before all that, there’s still an entire month to get through!

Whatever you’ve got planned for December, and whether you’re celebrating with friends, family, or alone, I hope you have a very Merry Christmas. And please check back from time to time, as I’m always finding new things to talk about here on the website! Hopefully this playlist has given you one or two ideas for what to listen to as you hang up the lights and decorate the tree, or for your next Christmas party. Cheers, and happy holidays!


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.

A Festive Playlist To Get You In The Holiday Spirit!

This is now the fifth year in a row that I’ve published my festive playlist – so let’s celebrate a half-decade of Christmas songs in style!

I’m a big fan of Christmas and this time of year; it’s my favourite holiday. There’s so much to love about Christmas from the food to the decorations, and music is also a huge part of that. I’ve been a collector of Christmas albums for years, since well before my music collection was digital! And in that time, I’ve discovered more than a few favourites that I welcome back at this time of year.

A photograph of a snow-covered road through some trees, with fairy lights on a fence on one side.
I hope you’re having a wonderful start to the festive season!

This festive playlist is really “part five” – and you can find the first four parts linked below. If you think a particularly famous track is missing… try checking out those earlier editions of my festive playlist. If it’s nowhere to be found, then I guess you’ll have to come back next Christmas! Is that the first time you’ve seen someone mention Christmas 2025?

Here are the previous playlists for you to enjoy:

2020’s Edition, 2021’s Edition, 2022’s Edition, and 2023’s Edition!

A photograph showing a horse (or perhaps a reindeer) pulling a sleigh through a snowy forest.
Dashing through the snow…

All of the songs linked below are hosted on YouTube. If for some reason one track or another is unavailable in your part of the world, I daresay you’ll be able to find it on another streaming platform. Take a listen to all of these songs in turn, or add them together with the playlists linked above and you’ll be all set for your next Christmas party or holiday event!

Let’s jump into this year’s edition of the playlist!

Track 1:
Buy Me Presents – Sabrina Carpenter (2023)

2024 has been, without question, Sabrina Carpenter’s year! The pop star has been riding high with tracks like Taste and Espresso, as well as headlining a world tour. But just last year, Carpenter released her first Christmas EP: Fruitcake. The track I enjoyed the most is Buy Me Presents: a tongue-in-cheek Christmas song with more than a few festive puns and double-entendres!

Buy Me Presents wasn’t released as a single, so it hasn’t charted on its own. But Fruitcake grazed the lower reaches of America’s Billboard 200, and also peaked at number 63 on the UK charts last year. The entire EP is well worth a listen, but if (like me) you find your festive playlist is getting over-stuffed and you only have room for one track, go with Buy Me Presents. It’s a ton of fun!

Track 2:
Baby, It’s Cold Outside – Jimmy Buffett feat. Nadirah Shakoor (2016)

Despite lyrics that have been controversial in recent years, I gotta confess that I love Baby, It’s Cold Outside. It’s a Christmas classic… but this version inverts the male and female lyrics, making for a very interesting and unique presentation. By “gender-bending” the lyrics, the tone of the song feels completely different to any other version I’ve heard, and when you add into the mix Buffett’s vocals and some tropical rock instrumentation, I think it makes for a really fun take on a song that many different artists have covered.

I’m not the world’s biggest Jimmy Buffett fan, but his two Christmas albums have both had fun takes on traditional and modern festive hits. This version of Baby, It’s Cold Outside wasn’t released as a single and didn’t chart – but the album ‘Tis the SeaSon, from which it’s taken, peaked at number 6 on both Billboard’s Country and Rock charts.

Track 3:
Santa Claus Is Comin’ To Town – Bruce Springsteen (1975)

Bruce Springsteen and his E-Street Band recorded a live version of the Christmas classic Santa Claus Is Comin’ To Town way back in the mid-1970s… and it’s been a mainstay on the radio seemingly ever since! I first encountered this version when I was living in the United States, but it’s not uncommon to hear it here in the UK, too. It’s a great cover, with Springsteen’s distinctive vocals bringing the song to life.

The live recording is best-known, perhaps, for Bruce Springsteen struggling to keep his composure! Santa’s refrain of “ho ho ho!” in the background seems to send Springsteen into fits of laughter – but that just adds to the fun, light-hearted nature of this recording. This version regularly re-enters the charts thanks to streaming and airplay, and is certified platinum in the US and UK.

Track 4:
Deck the Halls – André Rieu (2012)

I don’t know if you do this too, but I tend to keep instrumental tracks in separate playlists from songs with lyrics. But if I’m in the mood for a stirring rendition of one of a number of traditional Christmas carols, I often turn to André Rieu. The Dutch conductor and violinist has put together several Christmas albums over the years, including 2012’s December Lights.

I’m drawn to this particular arrangement because of how traditional it feels. I love different takes on the classics, don’t get me wrong, and there’s a time and a place for experimentation – as you’ll have already seen on my festive playlists so far! But sometimes what I want is a classic, up-tempo, orchestral arrangement of a traditional carol – and Rieu delivers.

Track 5:
Santa Baby – Michael Bublé (2011)

Michael Bublé is a singer who, not unlike Mariah Carey, has become synonymous with Christmas for a lot of folks! And it’s true that his 2011 festive album, simply titled Christmas, has a lot of excellent songs – but I don’t consider him to be a one-hit wonder (or a one-season wonder, I guess) because I’ve also enjoyed some of his other trad-pop hits over the years. But this version of Santa Baby? Oh boy, is it something different!

I cannot properly express in words how ridiculous it is to hear lines like “I’ve been an awful good guy,” and “Santa Buddy” as Bublé awkwardly tries to change the words. It’s done with tongue firmly embedded in cheek and a healthy dose of self-awareness – at least, I hope so – and it really is a ton of fun. Santa Baby is a song written for a woman (the original version was performed by Eartha Kitt in the ’50s) and its lyrics really don’t work so well for a male singer! Somehow, however, Bublé’s silly and awkward changes just… make the song so much more enjoyable for me. If you haven’t heard it, give it a try!

Track 6:
Christmas Alphabet – Dickie Valentine (1955)

Here’s a trivia question for your next pub quiz: what was the first Christmas-themed song to be number one on the UK chart at Christmas? The answer: Christmas Alphabet by Dickie Valentine all the way back in 1955! In those days, collecting information about record sales wasn’t straightforward, but it’s generally agreed that we have solid data from 1952 onwards. The first few songs to top the charts at Christmas weren’t Christmassy – but then along came Dickie Valentine!

Christmas Alphabet was Valentie’s second and final UK number one, though he remained active as both a singer and TV host well into the 1960s. Although this isn’t my favourite festive hit – and it’s one I don’t remember hearing in my childhood – I think it’s a neat little piece of history, and a pleasant traditional pop song from an artist of the pre-rock and roll era that I’m happy to listen to at this time of year.

Track 7:
Santa Tell Me – Ariana Grande (2014)

Ariana Grande is currently riding high at the cinema, starring in the film adaptation of Wicked! Ten years ago, though, her festive song Santa Tell Me was going platinum all over the world. I can’t believe it’s been ten years, because to me this is another of the “new” Christmas songs that I feel I’ve only just started listening to! But time is funny like that, I guess, especially at this time of year.

Santa Tell Me isn’t actually Ariana Grande’s biggest hit. It wasn’t 2014’s Christmas number one in the UK (it peaked at number 8 the week before Christmas) and the only chart it topped was Billboard’s Holiday 100 in the USA. But Santa Tell Me has re-entered the charts every year since its release thanks to streaming, and is a mainstay on playlists like this one! For my money, the track is fun, light-hearted, and festive, and I’m happy to return to it every holiday season.

Track 8:
You’re Christmas To Me – Sam Ryder (2023)

You’re Christmas To Me is up there with Ed Sheeran and Elton John’s Merry Christmas as one of my absolute favourite festive tracks from the last few years. It’s a pop-rock anthem that doesn’t feel a million miles away from the mega-hits of artists like Slade and Wizzard, and I firmly expect to see it as a mainstay on everyone’s festive playlists from this point on!

It’s such a shame that You’re Christmas To Me didn’t make it to the top of the charts. It was pipped to the post last year by Wham!’s Last Christmas surging as the big day approached… and I fear that Sam Ryder was screwed over by his exclusivity deal with Amazon Music. Had the song been more widely available, I genuinely think it could’ve been last year’s number one. Live and learn, eh? Maybe this year, with the exclusivity gone and the song available on other platforms, it’ll get a second chance?

Track 9:
Christmas In England – The Woodenheads (2008)

This track is… a bit of an oddity, to be honest with you. I bought the digital download of this song the year it was released, and it’s been part of my festive playlist going back to 2008. But I can’t find any information about the song or the band that created it. The YouTube channel for “The Woodenheads” only has this one song, and as far as I can tell the band never recorded nor released any other music. There is a different band called Woodenhead, but it’s based in the United States and the two are – as best as I can tell, anyway – completely unrelated.

Despite never charting, Christmas In England is a pleasant, somewhat nostalgic track. It recounts a typical English Christmas; the kind I remember from my youth. The lyrics talk of a grey, wet Christmas spent at home with the family and a bit too much roast turkey. Maybe The Woodenheads will be pleased to know that at least one person out there still remembers the song and listens to it with fondness every Christmas.

Track 10:
Happy Xmas (War Is Over) – John Lennon and Yoko Ono (1971)

Only a year after the break-up of the Beatles, John Lennon very nearly topped the charts with this perennial festive favourite. Happy Xmas (War Is Over) was actually beaten to the number one spot in Christmas week by a novelty song: Ernie (The Fastest Milkman In The West) by Benny Hill. That’s a trend that seems to continue to this day; in what other country would five songs about sausage rolls top the charts at Christmas time?

Of the big festive hits from the ’70s, I confess that Happy Xmas (War Is Over) probably isn’t my favourite. But it’s one of those nostalgic tracks that plays on repeat in faded memories of decorating the Christmas tree while my dad’s old record player blasted out Christmas hits! Themes of peace and joy are important at this time of year, too, and that’s something John and Yoko delivered with this track.

Track 11:
Sleigh Ride – Jewel (2013)

I’ve been a fan of Jewel since the ’90s, when her debut album Pieces of You introduced me to her incredible songwriting and vocals. Since then, Jewel has released two Christmas records, both of which are comprised primarily of new arrangements of traditional festive favourites. Both records are worth listening to in their entirety – but on this occasion I’ve picked out Jewel’s rendition of Sleigh Ride.

Sleigh Ride was first published in sheet music form in the late 1940s, and there are several versions that can all claim to be the “original” recording! There have been many takes on the cute festive track over the years, but for me, it feels especially well-suited to Jewel’s vocal style and folky presentation. This version wasn’t released as a single, but the album Let It Snow: A Holiday Collection made it into 2013’s top 20 holiday albums in the United States.

Track 12:
Rockin’ Around The Christmas Tree – Mel & Kim (1987)

Rockin’ Around The Christmas Tree is a great song – but if you’re British and in your forties (or younger, I guess) chances are it’s this version by Mel Smith and Kim Wilde that’s the most memorable! This version was recorded to raise money for the charity Comic Relief. The song and video both have comedic moments as a result – and even the name “Mel & Kim” is a parody of another popular act of the late ’80s.

In 1987, there was some stiff competition on the charts! The indomitable Fairytale of New York by The Pogues and Kirsty MacColl was that year’s number two – the number one spot went to Always On My Mind by the Pet Shop Boys… a much less Christmassy number! That left Mel & Kim to claim the less-impressive Christmas number three spot, but the song has been a favourite of mine since I heard it as a kid. I recall my parents – my father especially – didn’t like this version of the song, but I think it’s clever, funny, and oh so nostalgic!

So that’s it… until next Christmas!

A photograph of an illuminated stall at the Christmas Market in Frankfurt.
Are you going to a Christmas market this year?

Another set of tracks has been added to the ever-growing festive playlist… and there are more on the horizon. I’m especially looking forward to Ed Sheeran’s upcoming single Under The Tree – which is part of the soundtrack to the Netflix film That Christmas – and will be released in just a few days’ time. Ed Sheeran was fantastic a couple of years ago with his collaboration with Elton John, so I have high hopes for that one!

We’ve also managed to avoid Mariah Carey and Wham! for the fifth year in a row! I don’t hate those songs; Last Christmas is definitely the better of the two for my money, but both are enjoyable enough at this time of year. But I feel they’re so over-played and feature on way too many playlists like this! Besides, it’s become a Trekking with Dennis tradition to skip both of those songs… so let’s see how long we can keep it up, eh?

Two of the original illustrations from Dickens’ A Christmas Carol.

This is just the start of the festive season, and I have a few other Christmassy ideas that may (or may not, time and procrastination depending) make their way to the website before the big day. So stay tuned for that!

All that remains to say is this: Merry Christmas! Whatever you’re doing, wherever you’ll be, and whoever you’ll be celebrating with, I hope you have a wonderful and festive Christmas this year.


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.

A festive playlist to get you in the holiday spirit!

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.

Merry Christmas, puss!

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!

Decorating the tree!

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.