Hey Everybody! by 5 Seconds of Summer - this came out when I was still living at the blind home, when I was in deep financial shit for overspending on junk food and stuff. This song was just very relatable to me. It was also partly responsible for making me change my ways, as I don't overspend as much anymore.
Complicated by Avril Lavigne - I was introduced to her by my peer tutor when I was a high school sophomore, and I still remember her playing this song for me. She was like "Try and guess the title"; being hearing impaired, I wrongly guessed "Conjugated" bc we were conjugating verbs in German at the time. lol why ya gotta go and make things so conjugated...
I Want It That Way by the Backstreet Boys - this takes me back to when I first started stanning them. I was in Girl Scouts, and our leader had bought us tickets to see them in November of '99. I remember being in her car as she tried to navigate herself into Kentucky (we were going to Lexington), a journey that made us miss the opening act. lol but I still had a blast at that concert!
Tearin' Up my Heart by 'N Sync - aka the gateway to my pop music fandom. I first heard it on the bus on the way to school and remember loving it enough to check them out. Their debut album was one of the first ones I bought with my own money, too.