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!

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.

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!

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!

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.

































