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There are lots of choices, but I'll fight you on this.
The Police were one of my absolute favorite bands in high school. Saw them twice: Ghost in the Machine and Synchronicity tours. (Not all that good either time, but better than some Sting solo shows which tended to be quite bad.)
I think The Police have aged pretty badly. I now prefer actual reggae to fake British white boy pseudo-reggae. Most of all, though, Sting's fake Jamaican accent just kills many of their songs for me. My favorite used to be "Every Little Thing she Does is Magic" but I can't hack the bullshirt patois: "Ev'ry ting she do jus' turn me on." fork off, you're an upper class English teacher.
Having said that, this still kicks ass.. or at least I'm giving massive credit for the Beat t-shirt. I've had at least three of those over the years.
Side note: all three of them should be slapped in the face for the reworked version they put on a greatest hits album years later. Wankers.
The Who falls into a tricky category for me because I want to pick something cool and obscure but I can't.
I love The Who. No band meant more to me in my teen years. I would love to pick something lesser known like "Tattoo," which is awesome, but the answer is "Won't Get Fooled Again" and it's not particularly close. I might make the argument that it's the greatest rock song period. (Second Who choice: "Love Reign O'er Me.")
Along those same lines, Springsteen has a million terrific songs but the best is "Thunder Road," which is an obvious and boring pick. I have everything Cheap Trick has ever done -- hundreds and hundreds of songs -- and the best by a mile is "Surrender," the hit song everybody knows.