Taylor Swift: The hilarious, honest and heartfelt meanings behind her biggest hits

As one of the most prolific pop songwriters of her generation, it's no wonder that Taylor Swift had a whopping 30 songs hit the Top 10 in the UK, with eight of her original albums and a further five re-recorded albums hitting the top spot in the UK charts!

Fans of Taylor's, AKA Swifties, love nothing more than combing through her poetic lyrics, hunting for hidden meanings and Easter Eggs - so we've taken the liberty of analysing some of her biggest and most beloved songs right here.

'Love Story'

She may have already released a full album by the time 'Love Story' came around, but this was the song that shot Taylor to fame and started her on her journey to becoming a household name around the world.

Released as a single on 15th September 2008, 'Love Story' appeared on Taylor's second album, 'Fearless' and peaked at Number 2 in the UK - and has since been certified 4x Platinum in the UK. Of course, there's also 'Taylor's Version' - the re-recorded version before she got ahold of her master recordings and the first of those to be released, coming out in February 2021.

As we've since found out from Taylor herself, she has a mild obsession with characters from the work of Shakespeare - and this particular song is all about Romeo and Juliet, who meet a rather sticky end in the original story... But not in Taylor's world! The song ends with the couple getting engaged and - presumably - living happily ever after.

'You Belong With Me'

Another early track from Taylor, 'You Belong With Me' is still considered by many Swifties to be part of her "country era", as the track was played on both mainstream pop and country music outlets.

Released on 20th April 2009 and also appearing on 'Fearless', the track broke into the Top 40 over here in the UK and has been certified 2x Platinum, with 1.2 million UK sales - faring a little better in the USA where it peaked at Number 2!

The track's lyrics see Taylor pine after a friend romantically with unrequited love, all the while questioning his choice of girlfriend, heard in lyrics like: ''Cause she doesn't get your humor like I do', and: 'Dreaming 'bout the day when you wake up and find / That what you're looking for has been here the whole time.'

The music video saw Taylor star as both the girlfriend and the lovelorn friend, with Lucas Till as the love interest - and happens to be the video at the centre of the 2009 MTV Video Music Awards controversy with Kanye West.

'We Are Never Ever Getting Back Together'

As the first single to be released from Taylor's fourth album, 'Red', the song 'We Are Never Ever Getting Back Together' helped the singer really blast onto the pop scene in August 2012 as she began her transition over from the country world.

Shedding those country roots, Tay shot to the top of the charts around the world with this pop banger, co-written by Taylor along with her regular collaborators, Max Martin and Shellback. It's pretty obvious from the title what the song's about - after multiple attempts at rekindling a relationship, the protagonist is DONE.

There are a fair few theories online about which of Taylor's famous ex-boyfriends this track is about - with Rolling Stone affirming that Hollywood actor Jake Gyllenhaal is the inspiration, whom Taylor dated on and off between October 2010 to January 2011.

According to 2013 biography Taylor Swift: The Platinum Edition, Taylor wrote the song in the hopes that the ex would hear it "a lot", reportedly adding: "It's the opposite of the kind of music that he was trying to make me feel inferior to."

She also apparently said: "It was a relationship where I felt very critiqued and subpar. He'd listen to this music that nobody had heard of ... but as soon as anyone else liked this band, he'd drop them." She even referenced this in the lyrics: 'And you would hide away and find your peace of mind / With some indie record that's much cooler than mine.'

Fans on Reddit concluded that Jake is well-known for his love of indie music - plus the fact that Taylor apparently wears a bracelet from him in the music video for the song.

'I Knew You Were Trouble'

Another single from 'Red', 'I Knew You Were Trouble' came out on 27th November 2012. The instant pop hit further cemented Taylor's push away from the country genre and into the pop sphere, with its catchy melodies and almost dubstep production in the chorus really tapping into the popular musical styles of the time.

Peaking at Number 2 in the UK charts, 'I Knew You Were Trouble' was kept off the top spot by will.i.am and Britney Spears' 'Scream & Shout', and has since been certified 3x Platinum in the UK. Tay re-recorded the hit as a 'Taylor's Version', releasing that version in November 2021.

Of course, fans have always speculated about which of Taylor's former beaus the track could be about - with theories online honing in on Jake Gyllenhaal again and John Mayer, but it's most commonly thought to be about Harry Styles.

The lyrics don't give anything away specifically or drop definitive clues about the subject, as heard in the chorus: 'I knew you were trouble when you walked in / So, shame on me now / Flew me to places I'd never been / Now I'm lyin' on the cold hard ground.'

However, Taylor did once appear to confirm it was about Harry. After her performance of the song at The BRIT Awards 2013, she spoke in an interview to The Sunday Times and discussed how she's able to channel her emotions while performing.

"You're balancing the analytical side of your brain, which is telling you where to go and how to go there," she explained, continuing: "With the other side of your brain, which is saying, 'Feel everything you're singing, and show it on your face. Feel everything exactly as you felt it when you wrote the song'."

She then added: "Well, it's not hard to access that emotion when the person the song is directed at is standing by the side of the stage watching." So there you have it!

'Shake It Off'

Taylor's transition into the pop genre was fully established with the release of her fifth album, '1989' - a nod to the year of her birth, with lead single 'Shake It Off' truly making her a household name upon its release on 18th August 2014.

Co-written with regular collaborators Max Martin and Shellback, Taylor spoke about the meaning behind the song in an interview with Rolling Stone: "I've had every part of my life dissected.

"When you live your life under that kind of scrutiny, you can either let it break you, or you can get really good at dodging punches. And when one lands, you know how to deal with it. And I guess the way that I deal with it is to shake it off."

She even endeared new fans to her with the brilliant music video, which saw Taylor take on various different dance styles, trying to find one to suit her, but discovering that she's better off "being herself" and dancing to her own beat.

Taylor spoke about the video to Rolling Stone in the same interview, saying: "I'm putting myself in all these awkward situations where the dancers are incredible, and I'm having fun with it, but not fitting in. I'm being embarrassingly bad at it. It shows you to keep doing you, keep being you, keep trying to figure out where you fit in in the world, and eventually you will."

The lyrics also see Taylor recognise other peoples' opinions of her: 'I go on too many dates / But I can't make 'em stay / At least that's what people say.' But by the second chorus, she begins to describe herself through her own lens: 'I never miss a beat I'm lightnin' on my feet And that's what they don't see,' later singing: 'I'm dancin' on my own / I make the moves up as I go / And that's what they don't know.'

Peaking at Number 2 yet again (being held off the top spot by Meghan Trainor's 'All About That Bass') but lasting for a whopping 26 weeks in the Top 40, it's also been certified 5x Platinum in the UK.

'Lover'

Following her hiatus in 2016-17, the subsequent hard-hitting sixth album, 'Reputation', AND her legal battles with Big Machine Records, Taylor entered her dream pop era and put out seventh album 'Lover' in 2019.

Releasing the title track on 16th August 2019 - one week before the album - Taylor introduced us to this brand new iteration of her sound. The dreamy, folky ballad struck a chord (literally!) with fans all around the world, and became an instant favourite for first dances at weddings everywhere.

That would be a box ticked for Taylor, who wrote the song specifically for that scenario - telling The New York Times in December 2019 that she'd been thinking "for years" about writing a song that "people who are in love would want to slow dance to," adding: "In my head, I had just the last two people on a dance floor at 3 am, swaying."

We can also hear her intentions in the lyrics of the bridge, where Taylor rewrites the traditional wedding vows: 'Ladies and gentlemen, will you please stand? / With every guitar string scar on my hand / I take this magnetic force of a man to be my lover / My heart's been borrowed and yours has been blue / All's well that ends well to end up with you / Swear to be overdramatic and true to my lover.'

There's also a nod to Shakespeare in there, where she sings: 'All's well that ends well to end up with you', and - as we know - Taylor is a huge fan of the playwright's work, having drawn on his writing as inspiration for many of her songs including 'Love Story' and 'The Fate of Ophelia'.

Taylor even reworked the song as a 'First Dance Remix', utilising the skills of an orchestra to give a fuller and more magnificent sound which was based on the arrangement she performed at the American Music Awards in 2019.

The original track didn't make it into the Top 10 in the UK, but it was certified 2x Platinum by the BPI - so it's pretty safe to say it's a fan-favourite.

'Cardigan'

As Taylor moved into her "cottagecore" era, fans certainly saw a different, more versatile side of her. 'Cardigan' was released on 27th July 2020 as the lead single from her eighth album, 'Folklore', which was written during lockdown of the COVID-19 pandemic and surprise-released with just a few hours notice from Ms Swift.

She wrote on Instagram: 'Most of the things I had planned this summer didn't end up happening, but there is something I hadn't planned on that DID happen. And that thing is my 8th studio album, folklore.

'Tonight at midnight I’ll be releasing my entire brand new album of songs I’ve poured all of my whims, dreams, fears, and musings into. I wrote and recorded this music in isolation but got to collaborate with some musical heroes of mine,' going on to list Aaron Dessner, Bon Iver, William Bowery (the alias of her then-boyfriend Joe Alwyn) and Jack Antonoff.

She also spoke about writing songs on the album from the perspective of other people, making up characters and storylines - which resulted in a love triangle between fictional people Betty, who is cheated on by James with August. 'Cardigan' is from the perspective of Betty, named after Blake Lively and Ryan Reynolds' daughter.

She said during an interview: "This is a song that's about long lost love, and looking back on it and how special it made you feel, all the good things it made you feel, all the pain that it made you feel."

We can see this in the lyrics: 'But I knew you'd linger like a tattoo kiss / I knew you'd haunt all of my what-ifs / The smell of smoke would hang around this long / 'Cause I knew everything when I was young / I knew I'd curse you for the longest time / Chasin' shadows in the grocery line / I knew you'd miss me once the thrill expired / And you'd be standin' in my front porch light / And I knew you'd come back to me.'

It's clear that Taylor's character of Betty was caught up in the heartbreak and disloyalty of the affair, saying that she had a feeling it wasn't the end for them and that's why she couldn't move on.

The track went to Number 6 in the UK, and has since been certified 2x Platinum by the BPI. It was also nominated at the Grammys for Song of the Year and Best Pop Solo Performance.

'Anti-Hero'

Taylor put out 'Anti-Hero' as the lead single from her 10th studio album, 'Midnights' - with both the single and the album released on 21st October 2022. She once again teamed up with Jack Antonoff, with both parties co-writing and co-producing the song together.

She spoke out about writing the song and what it meant to her in a video posted to Instagram a few weeks before the album and single were released. She said that hadn't "delved this far" into her "insecurities in this detail before".

She added: "I struggle a lot with the idea that my life has become unmanageably sized, and that I... Not to sound too dark, but I struggle with the idea of not feeling like a person. This song is a real guided tour throughout all the things that I tend to hate about myself.

"We all hate things about ourselves, and it's all of those aspects of the things we dislike and like about ourselves that we have to come to terms with if we're going to be this person," she continued, adding that she likes the song "a lot" because "it's really honest."

It's clear that she's listing off her insecurities in the lyrics, too, with lines like: 'I have this thing where I get older but just never wiser,' which could mean she thinks she doesn't learn from her mistakes as she ages.

Of course, we also hear her honesty in the chorus: 'It's me, hi, I'm the problem, it's me / At tea time, everybody agrees / I'll stare directly at the sun but never in the mirror / It must be exhausting always rooting for the anti-hero,' and fairly harsh on herself when she sings: 'Did you hear my covert narcissism I disguise as altruism?'

'Anti-Hero' also won Video of the Year, Song of the Year, Best Direction, Best Pop, Best Visual Effects and Best Cinematography at the MTV VMAs. It was also nominated for International Song of the Year at the BRIT Awards 2023, missing out to 'Break My Soul' by Beyoncé, and nominated for Record of the Year, Song of the Year and Best Pop Solo Performance at the Grammys.

It went to Number 1 in the UK, spending six weeks at the top spot and a total of 35 weeks in the Top 40. 'Anti-Hero' has also been certified 4x Platinum by the BPI - translating to a whopping 2.4 million sales in the UK!

'Cruel Summer'

Although it appeared on Taylor's seventh album 'Lover', which was released in August 2019, 'Cruel Summer' saw a huge surge in popularity after appearing in the setlist for her 'Eras Tour', and was then released as a single on 20th June 2023.

Collaborating once again with Jack Antonoff, the pair joined up with Annie Clark - AKA St. Vincent - Taylor spoke about writing the track at an album release party: "This song is one that I wrote about the feeling of a summer romance, and how often times a summer romance can be layered with all these feelings of pining away and sometimes even secrecy.

"It deals with the idea of being in a relationship where there’s some element of desperation and pain in it, where you’re yearning for something that you don’t quite have yet, it’s just right there, and you just can’t reach it."

We can hear this sense of turmoil in the lyrics: 'And I snuck in through the garden gate / Every night that summer, just to seal my fate (oh) / And I screamed, "For whatever it's worth / I love you, ain't that the worst thing you ever heard?" / He looks up, grinnin' like a devil.'

The track peaked at Number 2 in the UK charts, going on to be certified 4x Platinum by the BPI - translating to over 2.4 million sales in the UK alone.

'The Fate of Ophelia'

Taylor's latest release, 'The Fate of Ophelia', is the lead single from her 12th album, 'The Life of a Showgirl', both released on 3rd October 2025. The track debuted at Number 1 in the UK, and was certified Platinum by the BPI two months after its release.

Taylor came to speak to us on the album's release day in her first radio interview since 2019, telling us all about the meaning of this song. She told Hits Radio: "I just have this fixation on Shakespeare characters that I fall in love with and I can't stand to see them meet a tragic demise.

"I can't, I don't want that to be what happened to them because I'm like, wait, are you talking about Ophelia die? She died? What do you mean? I was really excited to see what happened with her and Hamlet. They seemed great. And I'm kind of going back to like the song 'Love Story', which I wrote when I was a teenager."

She continued: “I can't watch Romeo and Juliet not work out. What do you mean they both die? They don't in my version of things. So, it's like you just turn the movie off before the bad ending.

"But this is a little bit like that where 'The Fate of Ophelia' talks about how, you know, Ophelia was driven mad by love and it talks about the hook says like, you know, 'you dug me out of my grave and saved my heart from the fate of Ophelia'. It’s a love song and it's also just got one of the catchiest post-hook kind of sections that I'm pretty proud of."

She added to Magic Radio about the post-hook section: "When we wrote that in studio, I was like, 'Yes, this is why I do music'. Like the way I feel when this part of the song happens. But this is a song about feeling for a long time like you might have met a similar fate to Ophelia who was driven mad over the years slowly by love.

"And instead she, you know, I kind of give her a little bit of a wee reference her fate, but you talk about sort of someone saving you from that fate and like how euphoric that feels to look at maybe your past experiences with heartbreak and feel that you've been like rescued from that by this fortuitous turn of events where you ended up finding a person that changed that for you."

Taylor also released an incredible music video for the song, truly encapsulating the essence of the album and was such a high production that she even released it in cinemas, along with some behind the scenes clips.

The lyric: 'Keep it one hundred on the land, the sea, the sky / Pledge allegiance to your hands, your team, your vibes', is a reference to her American Football player fiancé, Travis Kelce. Taylor has previously stated the poignance of his football number, 87, adding up to 100 with her favourite number, 13.

'Opalite'

Although not released as a single, Tay discussed her 'The Life of a Showgirl' album track with Hits Radio on the album release day: "That song was so much fun to write. Oftentimes in life when we go through something that doesn't work out, whether it's in our personal life or in our friendships or in our career path, we look at it as this major setback, like we've taken a step back.

"But I’ve found that so many of those instances in my life have, based on how you respond to it, can catapult you forward in growth, in wisdom, in perspective.

"I think those are the things that I've tried to find to be the most attainable qualities and the most aspirational qualities in growing up. Can you react to certain situations in a way that benefits you and the people around you and acquire wisdom because of it?

"'Opalite' is a song about forgiving yourself for having gone through something that didn't pan out the way you wanted it to. All the perfect couples would look at you and say, 'When you know, you know, and when you don't, you don't'.

"It's giving yourself permission to not have it all figured out or not marry the first person you ever dated, stuff like that. I'm just happy that song exists and that chorus, I'm just stoked about how like absolutely infectious and borderline narcotic it is."

Scroll through Taylor Swift's incredible career timeline so far:

Read more:

Taylor Swift: All your questions answered on the singer-songwriter 🎶

Taylor Swift's albums: Facts and figures about her super successful records

Taylor Swift's re-recorded albums: Which has she released and which is next? 🎶

Want more music news?

Read more of the latest music news here.

• Taylor Swift