20 Years, 20 Songs

the soundtrack of the first 20 years of my life, in 20 songs

Today, on the 9th of July 2025, I turn 20.¹

Throughout the 20 years of my life, music has played an important and formative role. So I thought, to celebrate the music that has most shaped my life, I would create a playlist of 20 songs. To be clear, this isn’t a list of my 20 favourite songs (otherwise it would be a very different list), it’s a list of songs that have been the soundtrack to my life, for better or for worse. Whittling this list down to just 20 songs was way harder than I thought it was going to be. I tried my hardest not to include an excessive amount of Taylor Swift, but even still, six of the twenty songs are Taylor songs. I’m not sorry about it. If I wanted to, I could easily make an entire list of 20 Years, 20 Songs (Taylor’s Version).

But without further ado, let’s get into the list.

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1. Let Her Go - Passenger

I’m not quite sure why, but I was obsessed with this song as a child. It came out in 2012, so I would’ve been 7 at the time. This one, Jar of Hearts, and Fireflies are the songs I distinctly remember my younger self loving (I’m not sure what that says about me). Now whenever I listen to this song, it makes me feel a bittersweet nostalgia in a way no other song does. Even now, I still think it’s a great ballad. The lyrics are simple yet effective. This song will always have a special place in my heart, and it definitely needed a spot on this list.

2. Clean - Taylor Swift

If you were to ask me my favourite Taylor Swift song, I’d probably say this one. 1989, while now far from being my favourite Taylor Swift record, is still an album that will always have a special place in my heart. My Mum bought a 1989 CD at a petrol station back when it came out; little did she know the floodgates she was opening.

1989 wasn’t only the first Taylor Swift album I ever listened to, it was the first album I listened to ever. I very quickly became obsessed with it. I would play the CD every time we went in the car, to the point where everyone else in my family grew incredibly sick of it. Up until that point in my life, the only kind of music I listened to was that of those around me. My Mum loved listening to her old 90s favourites, like Spice Girls and The Chicks, my Dad loved old grunge bands like Nirvana and Pearl Jam, my brothers listened to hip hop artists like Eminem and Kendrick Lamar. But 1989 was the first time I had something that was my kind of music. Just mine.

Clean was always a song on the album I loved, but it grew more special to me as I got older and started to understand the story behind the song. While Taylor’s relating it to a heartbreak, I’ve seen many people interpret it in so many different ways — getting sober, getting back on track after mental health struggles, getting through grief. This is such a universal song. Overall, it’s a song about healing. Definitely one of Taylor’s best closing tracks. I love Imogen Heap too; I’d kill for Taylor to work with her again.

3. My Shot - Hamilton

I first discovered Hamilton as a musical-theatre-loving 14-year-old in April of 2019. The first three songs off the soundtrack I heard were Non-Stop, Alexander Hamilton, and this one. As wordy as it is, I could still recite the lyrics to all 5 minutes and 33 seconds of this song in my sleep. If I had to point to the song that best showcases how much of a lyrical genius Lin Manuel Miranda is, it would be this one. The amount of motifs, the intricate rhyme schemes, the way the word “shot” is used to mean a chance, a shot of alcohol, and a shot of a gun all at once — it makes my English Major heart swoon.

4. Mockingbird - Eminem

When I was a kid, my Dad used to sing the Hush Little Baby nursery rhyme to me constantly. Although he used to switch the last line to, “and if that diamond ring turns to brass, daddy’s gonna kick the jeweler’s ass.” Charming man, my father. I was surrounded by a lot of Eminem’s music growing up, not just from my brothers, but also from my Dad. Little Me was always amazed by this song in particular, because I thought Eminem was singing Dad and I’s song. I have my gripes with Eminem now, but when he actually tries, he can write. The story he tells in this song is heartwarming and heartbreaking at the same time. Another song that fills me with so much nolstalgia every time I hear it.

5. Blank Space - Taylor Swift

Every Swiftie remembers the first Taylor Swift song they fell in love with, and for me, that song was Blank Space. This is the song that made me a fan. I was 8 years old when it came out. I have no idea why, but Little Me was obsessed with this song. I used to watch the music video obsessively too. I distinctly remember that it was the first song I memorised all the words to, and I was so proud of myself for doing so. Of course, the satire of it all went completely over my head as a kid, but now I see this song for the lyrical masterpiece it is. She was mocking the media and public after years of them taunting her and making her out to be some crazy, unhinged serial dater. And let’s not forget how much of a chokehold, “darling, I’m a nightmare dressed like a daydream,” had on literally everyone. I’m not afraid to say: one of the best pop songs ever made.

6. If I Could Fly - One Direction

I think a One Direction phase is mandatory for all late millennial/early Gen Z girls. I didn’t have my One Direction phase until after they had split up (sorry, “hiatus”). I remember one night in 2018, when I was 13, my older cousin filled me in with all the lore of the band. I listened to all the albums. I listened to all the solo albums. I would watch old performances and interviews on YouTube all the time. I think One Direction made a lot of generic, bland pop music in their time, but they also made some damn great pop songs. This is an example of one of their best. It’s just a really simple yet beautiful love ballad. When I was 14, I used to always say this would be my wedding song. It felt deserving of a spot on this list for that reason.

7. Last Kiss - Taylor Swift

I mean, I had to include this song. My biggest flex as a Swiftie is that my birthday is July 9th, aka, Last Kiss Day. For a long time, it was the only date Taylor specifically mentioned in a song, up until High Infidelity’s April 29th came along and ruined everything. Yes, this song is special to me because she says my birthday in it, but I also genuinely love everything else about it; the production, the lyrics, the build-up. This song is a slow burner, you have to let it sweep you up so you get that emotional payoff in the bridge.

I also have certain memories associated with this song. It was August of 2020. I was 15. Restrictions in our state had eased up, so my family decided to take a trip up the mountains, as it was forecast to snow. I am not from a place where it snows,² so I could count the number of times I’ve seen snow before on the one hand. It was always a dream of mine, however, to watch snow fall. When we went on this trip, Taylor had only just dropped folklore. I made a playlist for the trip, which included all of folklore, but also Last Kiss. I have a very specific memory of sitting in the boot of a seven seater car parked in the gravel carpark of a pub in some middle-of-nowhere town, wrapped in a puffer jacket and a beanie, listening to this song.

It ended up snowing a lot on that trip, and I finally got to watch snow fall. Last Kiss is now forever a snow song to me. And even though Taylor herself has declared folklore a summer album, I’ve always seen it as a winter album because of that trip. You can’t know how much of a winter album it is until you’ve listened to it while snow is falling all around you.

Some memories from that trip.

8. I Did Something Bad - Taylor Swift

The year is 2017. I am 12 years old. Taylor has just dropped Reputation. I still so vividly remember listening to this album for the first time on the floor of my friend’s bedroom as she played it on her CD player. As with 1989, it was love on first listen. The very next day, I went out to Target³ and spent $20 on my very own Reputation CD; and keep in mind, when you’re 12, $20 is a lot of money. Just as I had with 1989, I played that damn Rep CD every time we went in the car.

For many years, I Did Something Bad was my favourite Taylor song. In complete honesty, part of why I loved this song is because it made teenage me feel like a badass. As with Blank Space, it wasn’t until I was older that I fully understood the satire of this song. I Did Something Bad truly is the darker, more cynical older sister of Blank Space. On Blank Space, she’s playing into the narrative of her being a cliche crazy ex-girlfriend. On this song, she’s playing into the narrative of her being a cold and apathetic master manipulator.

The live performance of this song on the 2018 Reputation Tour quite literally altered my brain chemistry. That performance lives in my mind rent free. Even after the Eras Tour, I still attest that is her best live performance to date. The biggest misfortune of my life will forever be that 13-year-old me couldn’t find anyone to take her to the Reputation Tour. Even all these years later, Reputation is still my all-time favourite album, and I think it always will be. Everything about that era has such a special place in my heart; the music, the videos, the tour, the story behind the album — everything.

9. Burn - Hamilton

In order to include all the songs I wanted to, I had to limit myself to only 2 Hamilton songs, so please just know it absolutely killed me to cut Satisfied and Wait For it from this list. In my heart, those songs are on the list. But of the three, I knew Burn had to be on this list. This is such a great ballad. The production starts out minimal and simple, but then it builds and builds, mimicking Eliza’s sadness morphing into anger. It is also such a beautifully written song (shameless plug, I know, but I have written a lyrical analysis of it, if you’re interested). It helps that Phillipa Soo has the voice of a literal angel.

In November of 2022, when I was 17, my Mum took me to see Hamilton live in Melbourne as a late birthday present. As soon as I found out the show was coming to Australia, I wouldn’t shut up about it. We went on a weekend, so we had a majority swing cast, but they were still incredible. Our Alexander was Tainga Savage and our Eliza was Martha Berhane. I wish I could say I remember more about the show, unfortunately I was so excited I mentally blacked out for most of it, but I do remember Tainga and Martha doing amazing jobs as their respective roles.

Some photos from my show.

10. drivers license - Olivia Rodrigo

I still think this is the song of 2021. It was everywhere. It was unavoidable. Everyone was wondering who this girl was, and where she had come from. I was one of the few who knew of Olivia from before her drivers licence fame. I watched her on Disney Channel back when she was on that weird show Bizaardvark, and then later when she played Nina on High School Musical: The Musical: The Series. I was 16 when SOUR came out, and something about the teenage angst of that record spoke to my soul, especially on songs like brutal and jealousy, jealousy.

When GUTS came out, I was 18, and in my final year of high school. I have very distinct memories of walking through my hometown on my lunch break or my free period, playing GUTS in my earphones. Again, being in the exact right age bracket, songs like teenage dream, ballad of a homeschooled girl, making the bed, and pretty isn’t pretty really spoke to me. drivers licence isn’t necessarily my favourite Olivia song, but I chose it to represent her on this list because it’s where it all began. I listened to this song obsessively in 2021. One reason why Olivia feels different to me compared to most of my other favourite artists is because of that closeness in age. She’s only 2 years older than me. I love that I’m getting to grow up and mature with Olivia and her music, something I didn’t get to do with artists like Taylor and Lorde. I also love that with Olivia, I’ll always be able to say I was there from the very beginning. I cannot wait to see what she does next.

11. Ribs - Lorde

I couldn’t not include at least one Lorde song on this list. And what better song than the one that perfectly captures the experience of realising childhood is coming to an end? This is the most beloved song on Lorde’s discography for a reason. There are few songs that are as relatable and touching to me as this one. The lyric, “my mum and dad let me stay home, it feels so scary getting old,” gets me every time. I love the childlike innocence in the bridge, declaring they’ll laugh until their ribs get tough, before reality sinks in that it’ll never be enough. No matter how much she wants it, the blissful joys of youth and childhood will never return (another shameless plug, but I have also written a lyrical analysis of this song in the past). Other than Taylor, Lorde is probably next in line of being the most formative artist of my life. All four of her albums are very important to me.

12. Ex-Wives - SIX: The Musical

This song is the opening track of what is my second favourite musical after Hamilton. I first listened to the SIX soundtrack in 2020 and became absolutely obsessed with it. The entire musical is based around this wacky yet fun concept: what if the six wives of King Henry the 8th formed a pop girl group? Each queen gets their own song, where they get the chance to tell their story. I don’t know why my two all-time favourite musicals are both based on important historical figures, but they are. This musical is fun, and camp, and light-hearted, but also serious at the right moments as well. There’s a lot of underlying feminist themes; both in the actual songs and the mere fact that the show has an all women cast and an all women band. My personal favourite song off the soundtrack is actually I Don’t Need Your Love, but I chose Ex-Wives for this list because it feels more representative of the show as a whole. SIX did gain a lot more popularity after it hit Broadway in 2021 (it originated on the West End), but I still think it is such a severly underrated musical.

13. Paciencia Y Fe - In The Heights

I’m still not over this gorgeous, gorgeous song. I was late to In The Heights; I really only got into it once the film adaptation came out in 2021. I’m just obsessed with the way Lin Manuel Miranda tells stories through music. This song, in particular, is my favourite song off the soundtrack. It’s the most touching song of the musical, where this elderly character who acts as everyone in the neighbourhood’s grandmother finally gets to share her story. I think part of the reason why this song is as touching to me as it is is because it reminds me of my great grandmother in some ways; who, while not Hispanic, was someone who immigrated from Europe over to Australia in her early adulthood, and who also had to deal with poverty and working manuel labour jobs for years, while also learning English, just like Abuela Claudia speaks of in this song. In my opinion, this musical deserves just as much love as Hamilton gets; there are multiple songs on the same level of greatness.

14. All Too Well (10 Minute Version) - Taylor Swift

Listening to the 10 minute version of All Too Well for the first time on that fateful November afternoon in 2021 was an experience I’ll never forget. If you know anything about the TSU (Taylor Swift Universe), then you know there isn’t a single other song on her discography that has as much lore as All Too Well. A track 5 hidden on Red, not a single, no music video, and yet it became both the fan favourite and the critic favourite. For years, there was speculation and mystery around the supposed original demo of this song that was 10 minutes long⁴. Finally getting to hear it after all that time was surreal. All Too Well isn’t my absolute favourite Taylor song, but if you were to ask me which song of hers best demonstrates her ability to tell a story within a song, I would point you to this one. You can’t listen to this song and tell me she isn’t a master storyteller. Getting to hear the entire 10 minute version of this song live at the Eras Tour was an out-of-body experience; such a phenomenal song live.

it was rare, i was there, i was there.

15. The Chain - Fleetwood Mac

I truly believe this is one of the greatest songs ever made. One thing my Dad and I bond over is our shared love of music, and we have an extensive Spotify playlist of songs we both love. This is one of our favourites. This is the one we blast as loud as it can go over the speakers when we’re in the car. The drums, the vocal delivery, the bass solo that morphs into an electric guitar solo — everything about this song is pure musical excellence. Fleetwood Mac are one of the best to ever do it for a reason.

16. American Pie - Don McLean

This song is on the list purely because I have a very specific memory associated with it. Back in February of this year, my grandparents sold their house. It was the house they’d lived in for 40 years, so my entire lifetime. I loved that house. I loved that house more than my actual house. Every corner of that house was steeped in memories from every era of my life. To say I was devestated to be saying goodbye to it would be an understatement.

It was the night before the keys had to be turned in, and my Mum and I had stayed behind to deep clean the house. By that point, all the furniture had been removed and we were scrubbing the walls of a now empty, hollow house. It was late, and I was emotionally exhausted, so I laid on the floor like a starfish in the middle of the empty living room and stared up at the ceiling. We had been playing music while we cleaned, and American Pie came on shuffle. I let all 8 minutes of it play. Certain lyrics really hit me in that moment, especially, “this will be the day that I die,” because I felt like a part of myself was dying that day.

As I was laying there, staring up at the ceiling, listening to the cinematic song that is American Pie, on the precipice of saying goodbye to my childhood home, I felt like I was in a scene of a movie. Now whenever I listen to this song, it takes me right back to that moment. Suddenly all the emotions come rushing right back, and it’s like I’m saying goodbye all over again.

17. Dancing Queen - ABBA

I don’t think there’s a single other song that exists that makes me as happy as this one does. It’s the ultimate pick-me-up; no matter how sad I may be, I know this song will get a smile out of me. And doesn’t this song have that effect on everyone? Any time I’ve been out somewhere, and this song has come on over the speakers, best believe everyone will be up on their feet in a matter of seconds. But of course, I can’t talk about any ABBA song without talking about the Mamma Mia of it all. My love of ABBA stemmed from watching the Mamma Mia movie a few years back, which has gone on to become my ultimate comfort film.

18. Cruel Summer - Taylor Swift

I wanted to include this song on the list because to me, this is the Eras Tour song. I have loved this song since 2019, back when we considered it to be an underrated gem on Taylor’s discography. With it now sitting at 2.9 billion streams on Spotify, I don’t think I can call it an underrated gem anymore, and it has the Eras Tour to thanks for that. Whenever I listen to this song now, all I can see is Taylor in that goddamn iconic pink and blue bodysuit, strutting across the stage. Whenever I listen to this song now, suddenly I’m back in that stadium, screaming “I love you, ain’t that the worst thing you’ve ever heard?” at the top of my lungs alongside 96,000 other people.

When I look back on the 20 years of my life, attending the Eras Tour last year is a standout moment. I am not being dramatic when I say it was the best day of my life. It was the first concert I had ever been to, and it only felt right that my first concert should be the artist who has indefinitely been the most important musical artist of my life. I have been a Taylor Swift fan since I was 8 years old. I have quite literally grown up with her music. My teen years were rough, but always there, as a form of comfort and a beacon of light, was Taylor’s music. So getting to attend the Eras Tour was unbelievably special to me, and Cruel Summer will always take me back to that day.

19. That Funny Feeling - Bo Burnham

2021 was not a good year for me. I had debilitating anxiety, social anxiety so bad it was borderline agoraphobia, and I was having constant panic attacks. I was, as Bo would put it, at an ATL (All-Time Low). You may remember that 2021 was the year Bo released his fourth comedy special, INSIDE. That special made me feel so understood. I had the soundtrack on repeat for months on end. To me, INSIDE perfectly captures what it feels like when your mental health is declining. It starts off as a comedy, but as the film progresses further and further, you watch as Bo slowly unravels, and you feel as if you’re unravelling with him. But there is no other song from the special quite like That Funny Feeling. It’s the only song where he isn’t trying to hide the grimness of reality behind jokes and humour. This song has a calming yet saddening effect on me. It is, simply put, a song about the end of the world. “That unapparent summer air in early fall, the quiet comprehending of the ending of it all,” is a lyric that never fails to hit me hard, and it has no right being a lyric from a comedy special, of all things.

20. I Know The End - Phoebe Bridgers

I can’t fully put into words the way this song makes me feel. But it is 5 minutes and 44 seconds of musical perfection. I’m pretty sure this song is the one they’ll play during the end credits when the world ends (two ‘the world is ending’ songs back to back, how fun). I am an absolute sucker for when songs start out slow but then crash and explode into a completely different song, and no song has ever done that better than I know The End. I could ramble on about why this song is so great, but honestly, I’d rather not over-explain it and just let it speak for itself. But considering the finale feel of this song, it felt appropriate putting it as the 20th and final song on the soundtrack to my life.

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Writing this, in all honesty, was more of an emotional rollercoaster than I thought it was going to be. It made me realise just how important music is to me and how important a role it has played in my life. And while whittling this list down to just 20 songs was an equivalent experience to pulling teeth, I overall had so much fun compiling this list and giving my reasonings behind each pick.

Until next yap,

- Lilly :)

1. I’ve even scheduled this post to come out at 12:06am (Aussie time) because that was the exact time I was born. Because I’m quirky and self-centred like that :) :)

2. except for the one time it did a few years ago. First time it had in over 50 years and they called it a freak of nature lol

3. back when you could still buy CDs at Target in Australia

4. There’s a really great Reddit thread that covers the entire history of All Too Well and every time Taylor talked about it in chronological order, I’ll link it: here.