A festive playlist to get you in the holiday spirit!

For the third year in a row I’m putting together a playlist of some of my favourite Christmas tunes! This playlist will perfectly complement the playlists I published in 2020 and 2021, so be sure to check out both of those to see even more holiday favourites!

I love this time of year, and revelling in Christmas music is one way to enjoy the season. Over the years I’ve amassed a collection of Christmas albums and singles, spanning a range of musical genres and styles. A lot of more modern albums seem to be comprised of the same handful of “traditional holiday favourites,” but every once in a while there’s a real gem amongst them – be that an original song or a great cover.

Christmas will soon be upon us once again!

Last year we were treated to Ed Sheeran and Elton John’s instant Christmas classic Merry Christmas, and that song will be a permanent fixture on my holiday playlist from now on! There are still original Christmassy songs composed, then, even if the charts have been dominated in recent years by talent show winners and novelty songs.

This playlist is really “part three” – following on from the playlists I’ve published over the past couple of years. So please go back and check out my first playlist, which you can find by clicking or tapping here. And don’t forget part two, which you can find by clicking or tapping here! Put all three together – or just pluck out your personal faves – and you’ll be set to go for your Christmas party!

The videos below are all hosted on YouTube, and some may be region-blocked. However, all of the songs should be available via your streaming method of choice if you can’t listen to them here. Let’s jump into the playlist!

Track 1:
Wonderful Christmastime – Paul McCartney (1979)

Was the ’70s the golden age of pop-rock Christmas songs… or is that just the nostalgia talking? After the likes of Slade, John Lennon, Mud, and Wizzard all put out songs that have become perennial favourites, Paul McCartney closed out the decade with Wonderful Christmastime. And apparently he hates it – or rather, he’s come to dislike the song after hearing it every Christmas season for more than forty years!

What’s fascinating about Wonderful Christmastime is that Paul McCartney composed the song, sings it, and also plays every single instrument you hear on the recording. His band at the time, Wings, wasn’t involved in the song at all (though members of the band do appear in the video). Whatever you may think of the song – and it’s definitely a love-it-or-hate-it Christmas track – a lot of work and talent went into its recording.

Track 2:
Up On The Housetop – The Jackson 5 (1970)

Up On The Housetop is one of those Christmas classics that seems to have been recorded by a wide range of performers! Originally composed in the mid-19th Century, the song tells a timeless tale of the arrival of Santa Claus on Christmas Eve. The Corporation, who produced many of the Jackson 5’s early hits, adapted the song for the group, adding in new lines for the Jackson family.

As an R&B/funk arrangement, the up-tempo adaptation of the song is pitch-perfect, and the extra lines add a little dash of humour. It’s not a straight cover of this Christmas classic – but there are many other arrangements of Up On The Housetop that stay true to its original composition. For my money, the Jackson 5 version is one of the better ones, and certainly one of the most unique.

Track 3:
21st Century Christmas – Cliff Richard (2006)

21st Century Christmas was Sir Cliff Richard’s last real effort to score a number one hit in the UK. If he’d succeeded, he would’ve been the first and only artist to reach the number one spot in six different decades, after achieving the milestone at least once in every decade from the ’50s to the ’90s. 21st Century Christmas managed to sell more CDs than any other song – but was pipped to the post by Take That in the week before Christmas and by X Factor winner Leona Lewis in Christmas week. Both artists achieved their positions thanks to downloads, which were newly-incorporated into the charts at the time.

Despite not quite hitting the top spot, 21st Century Christmas is a nice song, and it’s been a fixture on my Christmas playlist. I bought the CD single in 2006, and I bought the song again as an mp3 a few years later. Some of the lyrics feel rather dated as Sir Cliff’s idea of a 21st Century Christmas involves faxes and DVDs… but hey, they were modern and hip at the time! And it wouldn’t be Christmas without one of Sir Cliff’s songs!

Track 4:
Christmas Is All Around – Love Actually OST (2003)

Rom-com Love Actually didn’t really feel like a typical Christmas film when I first saw it, but it’s certainly become a perennial Christmas favourite over the past couple of decades! One of the film’s story threads followed ageing rock star Billy Mack – played by Bill Nighy – as he chases one last chance at stardom by scoring a Christmas number one with a Christmas version of Love Is All Around.

The song is deliberately silly, with some slightly awkward moments as the words don’t quite fit in time to the beat! But as a parody and pastiche of novelty Christmas songs, it’s absolutely perfect. And the end result is a perfectly creditable Christmas song in its own right – one that has managed to find a place on my Christmas playlist!

Track 5:
Santa’s Coming For Us – Sia (2017)

Australian pop superstar Sia released her first Christmas album in 2017 – and as a collector of Christmas albums, I snapped it up as soon as it was available! The lead single from a Christmas album that was made up mostly of new compositions was Santa’s Coming For Us, and it’s a fantastic modern Christmas song.

Santa’s Coming For Us topped the charts in Canada… but nowhere else, reaching a distant 17th place on the charts here in the UK. The music video features Henry Winkler (best known as Fonzie on Happy Days) as part of an all-star cast, which is kind of neat. I always like to give new songs a fair shot, and I’m definitely glad to have tried Sia’s Christmas offering.

Track 6:
O Little Town Of Bethlehem – Annie Lennox (2010)

In 2010, Annie Lennox (of Eurythmics fame) released her first Christmas album! God Rest Ye Merry Gentlemen – a fairly drab traditional carol – was the lead single, but for my money, Lennox’s arrangement of O Little Town Of Bethlehem is the real standout track. It wasn’t released as an independent single, though, so it never charted.

Traditional carols like O Little Town Of Bethlehem have seen many different arrangements and covers over the years. Lennox’s take is much more traditional than the Cliff Richard/Amy Grant song Little Town (which made the cut to feature on the 2020 edition of my festive playlist!) But I think there’s room to enjoy both classic and novel arrangements of the same festive favourites sometimes. Annie Lennox did a great job on O Little Town Of Bethlehem, and her version is, at least for me, one of the best.

Track 7:
Merry Christmas (Exclamation Point) – Jon Lajoie (2013)

Jon Lajoie’s song is a very light-hearted look at Christmas, and I absolutely love it! Merry Christmas (Exclamation Point) is incredibly relatable; we all have people in our lives outside of our immediate circles of family and close friends, work colleagues and casual acquaintances who we want to acknowledge over the holidays – but not in a big way! And that’s what the song is all about.

I confess that I’m not familiar with Jon Lajoie or any of his other work. I stumbled upon this Christmas song on iTunes or YouTube shortly after it was released, and I fell in love with its humourous take on the holiday season. It’s been a feature on my playlist ever since – and a song I’ve recommended to others, too!

Track 8:
Do They Know It’s Christmas? – Band Aid (1984)

Last year, I put Band Aid 20’s version of Do They Know It’s Christmas (from 2004) on my playlist, but as I said then, it’s a toss-up for me whether that version or the original from 1984 is better! So this year we’re going to add the original version! Band Aid came together very quickly in late 1984, inspired (or so the story goes) by a BBC news report on that year’s famine in Ethiopia. The song was thrown together in a matter of days by Bob Geldof and Ultravox’s Midge Ure.

Do They Know It’s Christmas? was a charity single, with all the proceeds raised going to help with famine relief in Ethiopia, and although some of the lyrics are a little on the nose, the intentions here were good. Band Aid went on to inspire the Live Aid and USA For Africa concerts in 1985 (the former of which is one of my earliest television viewing memories!) and the song itself has been re-recorded on three separate occasions now, raising more money for charity every time. And as a festive hit, Do They Know It’s Christmas? actually manages to be a good, enjoyable song.

Track 9:
Thank You Santa – Mitchel Musso (2009)

This song was featured on the Phineas and Ferb Christmas special in 2009 – specifically, it’s the song at the very end that plays while the credits roll. It’s an incredibly sweet song, and without wanting to put too fine a point on it, it’s all about saying thank you to Santa Claus!

Mitchel Musso voiced the character of Jeremy in Phineas and Ferb for all four seasons of the show (and its spin-off films), and was also a Disney Channel star, appearing in shows like Hannah Montana and Pair of Kings. This song has been a fixture on my Christmas playlist – along with several others from the same Christmas special – ever since I got the CD soundtrack!

Track 10:
Three Ships – Cyndi Lauper (1998)

Cyndi Lauper’s Christmas album in 1998 didn’t do especially well on the charts, but she brought a new style to several traditional carols. Her version of Three Ships is probably one of the more unique takes on the carol that I’ve heard, and as a lesser-known Christmas tune it’s nice to see songs like this given a new arrangement sometimes.

I Saw Three Ships is a traditional carol whose origins are lost, and speculation abounds as to what the titular three ships might have been carrying – and what their destination may have been! Regardless, the song seems to date to at least the middle ages, and although it isn’t at the top of everyone’s list, new versions and arrangements still pop up from time to time.

Track 11:
Stop The Cavalry – Jona Lewie (1980)

Stop The Cavalry is one of those songs that didn’t start out life as a Christmas song… but became one almost by default thanks to a December release! One line in the song mentions Christmas, but aside from that it’s really a protest song, an anti-war track that references the First World War but also looks to contemporary conflicts and the threat of nuclear war as well.

I’m certain that Stop The Cavalry would have reached the number one spot in December 1980 – possibly as that year’s Christmas number one – were it not for the murder of John Lennon that same month. Two of Lennon’s hits – (Just Like) Starting Over and Imagine – hit the number one spot in December and January, keeping Stop The Cavalry from topping the charts. In the years since, however, the song has become a well-known holiday favourite here in the UK.

Track 12:
To Christmas! (The Drinking Song) – Straight No Chaser (2016)

The story of acapella group Straight No Chaser is a fun one! The group was founded in 1996 by a group of students in Indiana, and they played a number of local gigs in the late 1990s before they graduated and went their separate ways. But in 2006, a video that had been recorded of their version of Twelve Days of Christmas years earlier went viral on YouTube, racking up more than twenty million views – massive numbers at the time! The band got back together and have since put out several albums.

To Christmas! (The Drinking Song) is a fun, light-hearted track taken from their 2016 Christmas album. The song races through the entire season, from the weeks leading up to Christmas right through to New Year, and it does so in a gentle and fun way, touching on topics like parties and Christmas shopping but with a neat, modern twist.

So that’s it!

Not long to wait!

We’ve added twelve more tracks to the festive playlist, and for the third year in a row we’ve managed to dodge both Wham! and Mariah Carey. That’s no mean feat… but will we be able to keep them at bay again next year? Tune in to find out!

Here in the UK, we’re looking at the third Christmas in a row that won’t be as enjoyable as we’d want it to be. Two pandemic-disrupted years have given way to a cost-of-living catastrophe, inflation, strikes, and a general sense that we’re in for a “winter of discontent” that could rival the late 1970s. At times like these, the light escape that Christmas music can provide is incredibly important to me. Stepping away from the difficulties of the real world, if only for a moment, can be just what the doctor ordered, and for me, Christmas music can provide that. It’s in that spirit that I share this playlist with you – and I hope some of the songs provide you with a little dash of festive enjoyment to perk up your holiday season.

With just over three weeks to go until the big day, I have a couple of other Christmassy ideas that may make their way onto the website – so I hope you’ll check back for those before Santa comes. I truly hope you’re making the best of the holiday season, whatever your circumstances may be.

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 claims, please contact YouTube directly. This article contains the thoughts and opinions of one person only and is not intended to cause any offence.