Matchbox Twenty is a band that I've grown to appreciate more over time, though
#185 "
3AM" was one of the first of their songs I started liking early on.
I am tremendously late to this party, but you're doing God's work.
My wife and I got to see Matchbox Twenty in concert about a year ago, and it was legitimately a great time. I'm not a huge fan of them (my wife's the one who bought all the CDs and campaigned to go to the concert), but they put on a hell of a show. A lot of heart, and a lot of songs I liked a good bit more than I remembered having liked them. Maybe it's just the live-show energy?
Anyway, I think "Bent" would have been my pick, but that song appeals to me in a way that takes some serious thought to articulate. There's something thoughtful, introspective, anxious, and a little bleak about that one, and that speaks to me more than I'm sometimes comfortable admitting. The image or concept that occurs most often to me when I listen to it (irrespective of the video, which I've never actually watched) is one of being out and about between places at some unholy hour of the night or morning (say... 3:00 a.m., maybe?), in between places and in between purposes.
Really, though, as a guy born in 1981, this thread is basically a long trip back to my junior-high and high school years. At least for the rock parts. I never got much into country, and my knowledge of pop and hip-hop is pretty anemic. My wife was more into those genres, so for long road trips we alternate CDs from each other's collections and wax nostalgic and tease each other about it. For me, though, basically my whole life up to somewhere in the early-mid 90s, I'd listened to whatever my parents had on. I had my radio set to a pop station because it was nice and inoffensive enough, and never budged the dial. Then one day I came across the video for Soundgarden's "Black Hole Sun," and between the sound and the visuals, radically unlike anything I'd ever seen in my life, it felt a little like having my third eye violently crowbarred open.
Also, it may not go on your list, but I would like to humbly submit the following (in the vein of introspective/anxious/bleak from before) as worthy: