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.
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!
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!
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?
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.
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