My top 25 songs from the first half of the 20s
I was at a WeWork in Mexico City in 2023 doing a zoom-Italian lesson when I was asked “What kind of music do you like?” In semi-conversational Italian, I responded by saying “I have the same taste in music as teenage girls. Harry Styles, Taylor Swift, Olivia Rodrigo, Troye Sivan…” and a burly, Mexican guy with blue and pink hair sitting at the table across from me started laughing. I looked over and he said “Io parlo Italiano” (“I speak Italian”).
I thought it would be a fun exercise to rank my top 25 songs from the first 5 years of the 2020s. Note: these are songs that came out in the first five years of the 2020s. In 2020, I discovered many songs from 2019, but they are not included on the list. Songs that came out in 2025 but I discovered in 2026 are also not on the list. It’s not totally fair, but I get to make the rules.
I definitely bias toward songs released while we were nomading (2022 - 2025). I think all the time on planes and on walks helped me hone my taste in music. I keep my playlists in chronological order to music discovery, and the playlists from 2020 and 2021 were all over the place.
I’m not going to try to make grandiose observations that apply to life, but I noticed two things:
I like songs more from periods where life was going really well vs when I was in a rough patch. Cruising around Greece or exploring Morocco or making gnocchi in Italy? Lots of great times. Business is struggling or we’re in an awful Airbnb with a bed two-sizes-too-small? Not many songs from that period.
Discovering Italian music really changed things. Plus, I was getting good at speaking Italian, so it was a combination of good times and good music.
My ranking system gets messy after spot 3. Definitely the top 3 are the top 3, though. The two classical songs I stuck at the bottom not because they’re the final two, but because I couldn’t compare them to anything else.
As It Was - Harry Styles
One of your Girls - Troye Sivan
Getting Older - Adam Lambert
So Long, London - Taylor Swift
Banish the Banshee - Isaac Dunbar
Save Myself - Ashe
Sweet Cherries - Finneas
Bang! - AJR
Cinema - Harry Styles
Storie Brevi - Annalisa & Tananai
Radiohead - Tananai
Medieval - Finneas
The Ballet Girl - Aden Foyer
Guarda Cosa Hai Fatto - Tananai
Escapism. - RAYE & 070 Shake
Booster - Tananai
I Can Do It With a Broken Heart - Taylor Swift
Father Figure - Taylor Swift
Oldies Station - Twenty One Pilots
Fantasmas - Humbe
Biale Inolvidle - Bad Bunny
The Diner - Billie Eilish
Actor - Conan Gray
IN A DREAM - Troye Sivan
La Perla - Rosalia
“Tuscany” Suite for Piano and Orchestra - Nicholas Brittel, Succession: Season 3
Succession - Andate Risoluto - Nicholas Brittel, Succession: Season 4
This is too small of a list so I allowed myself 27. Honorable mention to the songs I couldn’t add such as half the songs on Harry’s House, Olivia Rodrigo, Sabrina Carpenter, Isaac Dunbar, and KAROL G.
