I like The Man Behind The Slaughter by The Living Tombstone. I don't tend to enjoy fan-made music, but this one was too groovy to pass up.
Not necessarily a song but a whole sub-genre: Eurobeat. It started with Running in the 90s and I just went from there to listening and thoroughly enjoying pretty much the whole Initial D soundtrack.
1996-1997, Watched a VHS tape of a Chick Corea concert from the 80s. Cheesy as fuck jazz on stage. Laughing at the bad hair, and dated styling.
Suddenly I'm into jazz and listening to all sorts. Opened me up to some great musicians and great songs.
Probably Agenda Suicide by The Faint, because the music belies the dark hopelessness of people working office jobs hoping to achieve the American dream
https://youtu.be/xv8mJfDPxuA
It's not quite what you're asking, but I have had my perspective on a lot of songs changed once I actually looked up their lyrics.
My listening comprehension for music lyrics is piss poor. For any given pop or rock song I'd hear on the radio, maybe 70% of the time I find lyrics unintelligible. Clearly it's skill issue on my part, as the body of music listeners at large seem to have no problems understanding what they're hearing. I don't know how people do it.
Sometimes I'll catch enough words to throw into a search engine and get the song's title and lyrics, and maybe even a short blurb of context. That knowledge alone can make a song go from irritating noise to something I find rather pleasant.
I believe the most recent song I looked up and learned something about was Even Flow by Pearl Jam. It's a song about homelessness. Who knew? Fucking everyone, probably! But not me. For fifteen years all I heard was "FREEEEE-ZIIIIIN'..." and the rest just goes to mush. I also learned Even Flow is a completely different song from Plush by Stone Temple Pilots. The damn radio kept bamboozling me with that similar vocal progression they both have!
Ah well. Better on the bus fifteen years late than never on the bus at all. They say ignorance is bliss, but it's also the source of a lot of undue hatred. I find I hate far fewer songs when I actually understand what they're trying to say (if anything).
Of course, knowing doesn't magically fix all stinkers. I Love It by Icona Pop didn't get any better in my eyes when I found the lyrics for it. I find most pop country songs (which I am unavoidably subject to, living in the American midwest) don't have much novel or interesting to say, either. The closer I look, the more accurate Bo Burnham's Pandering becomes, and I hate it.
I guess the silver lining here is I get to lucky 10,000 my way through many of history's greatest hits. I'm sure many people would give a lot to experience something they like again for the first time. By virtue of my being absurdly late to the party, I get to do it every day.
I'm the same way, most song lyricsare incomprehensible gibberish. So you'll probably recognize this catchy line: "wrapped up like a douche in the middle of the night"
The theme song from Enterprise (“Where my heart will take me” by Russel Watson). So many Trekkies seem to hate this song but I genuinely love it. I normally skip through the intro songs to most Trek shows but this one I sit through every time (and I have the song in a number of my playlists).
Also Blood and Glitter by Lord of the Lost. Every year I listen to a playlist of Eurovision songs for fun. LOTL have stuck with me (and I’m going to see them live soon!!)
Because of Fallout New Vegas I got into songs about that like "Blue shadows on the trail" by Roy Rogers and that's like era of cowboy music that fits the theme if that aesthetic, even have a playlist for it, when I Play DayZ
I grew up on hip-hop never thought I'd be hearing this
Amour Plastique its that one from the stupid Napoleon memes, me and my friends made fun of them for a while until it just got stuck in my head
Started listening to Buddy Holly by Weezer ironically for the meme edits some months ago, now Weezer is my favourite band.