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Ed Sheeran reminds me of high school freshman year, because he's all that would play on the bus. Same with Meghan Trainor.
Certain country music songs remind me of middle school, because they would play on the school bus, I would fall asleep, and the songs would get stuck in my head all day.
I listened to so much cringey rap/hip hop in high school, it's actually kind of vivid because a couple weeks ago I went on a nostalgia trip on Spotify and listened to a bunch of 2008-2012 radio hits (and now my Daily Mix won't stop reminding me of all these terrible songs)
For example
Spoiler:
And honestly some of these I still think are good, but for the most part I'm just like 'huh, these lyrics are kind of terrible' when I listen back - yet there's still that nostalgic factor to them that just makes me really happy when I listen to them, so it's a bad-good kind of thing.