Wow. Very interesting question.
Styx and Journey are what started me off. Say what you will about cheesy, but Styx had a pretty broad cross section of musical style if you listened all the way through their albums. Journey is just an underrated band. Excellent musicians, Neal Schon is a fine guitarist, and has probably informed my taste in guitar from the get go.
Next up were the two bands that started me toward more complex and strange music: Jethro Tull and Blue Öyster Cult. Actually it was one song by each - "Cross Eyed Mary" and "(Don't Fear) the Reaper". While my taste has broadened considerably since 5th grade, you can always figure out if I will like a song by comparing it to those two. (If it doesn't compare, it doesn't mean that I won't like it, but if it does compare favorably, I am almost sure to.)
Next Up: AC/DC. Gave me an appreciation for Blues and started me toward metal. (I should note that Led Zeppelin didn't inform my taste so much as fit into taste that was already there from AC/DC and Jethro Tull.)
Next up: Rush and Iron Maiden - Between Geddy Lee and Steve Harris, I have always appreciated a good bass line. When I started liking these two bands, Rush's pedantic tendencies were more of a good thing than a bad thing, and, clumsy as they sometimes are, Bruce Dickinson's musical cliff notes approach to lyrics impressed me at the time. In any case, they prepared me to enjoy odd rhythms (Soundgarden, Zappa), to appreciate good bass work (Tony Levin), and to look for more of the hard stuff (Motorhead, Judas Priest, a ton of '80's hair metal. Strangely, I only recently started listening to Ozzy and Sabbath.)
I had a buddy in high school who turned me on to The Dead Milkmen and They Might Be Giants on the one hand, and REM and the Connells on the other. I like the silliness of the first two, which lead me to Dr. Demento, Julie Brown, Tom Lehrer, and Phish. It's hard to define what the other two did. Perhaps it involves making the kind of lyrical skill that I found in Jethro Tull, Rush, BÖC, and Maiden accessible to any kind of music, not merely the hard and complex.
Finally, there was the finishing off stuff in college: The Greatful Dead, Frank Zappa, Tom Waits, and King Crimson. Long Solos, Odd Intervals, Twisted Sensibilities, Gravelly Vocals, and assorted oddness.
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