I started out as a vidiot. Raised by the television, my music-loving journey started with the Partridge Family an Osmond Brothers records, and the Brady Kids were my first "live concert" at Six Flags when I was 10 or 11 years old right after their TV show was cancelled. My first "real" records were the Beach Boys Endless Summer and Loggins and Messina On Stage. I still listen to that L&M album, it's really good. Then I was given a copy of the Beatles Let it Be, and the rest is history.
I started listening to classical with my Grandmother, and also progressive jazz in college, but my first love was rock and roll. Listened to Nugent, Rush, Hagar, Travers, Zappa and early Van Halen in HS, Deep Purple; Zepplin and Sabbath before that, King Crimson, Genesis and Supertramp years later. I Also went through some intense phases with Bob Marley, Grateful Dead, and the Doors later on. I hated "pop" music early on like Steve Miller, The Eagles, Doobie Brothers and Elton John, but I learned to really appreciate that stuff years later.
Equipment wise, after my first record players (mono I think) I got a "killer" Pioneer Supertuner under the dash of my Vdubya in HS and listened to some great 8-track tapes until the stereo proceeded to eat them. Had a few other car stereos over the years, and my first taste of real stereo at home was a pair of Koss Pro 4AA headphones plugged into some kind of integrated amp/record player, I'm not sure what happened to them.
I had a roommate in college with Klipshorns, that definitely laid my audiophile foundation. I suppose he was my only audiophile influence, the rest was kind of stabbing in the dark until iLounge, and then Head-fi. I got his old Avid tower speakers and a Rotel Integrated amp and tuner combo when he was short on rent one month, which I combined with a Luxman P-405 turntable and a Nakamechi BX-100 cassette deck. I still have the Nakamechi in storage, and the Luxman is actually still online.
I moved on to early surround sound with a Yamaha 5.1 preamp and a Sony mofset power amp that must have weighed 80 pounds, it was a beast but it fizzled. It was replaced by an old but great sounding Kenwood integrated amplifier with a Sansui tuner as I was less than impressed by surround technology at the time. Then I got back into it with laserdiscs for awhile; I still have a bunch of them and a couple of players. I also discovered the joys of having a huge subwoofer at that time.
I lucked into a pair of scratch n' dent Sennheiser HD540 Reference II headphones at the local stereo store, and sent them in years later to get them repaired as one side had been cutting out intermittently. They were repaired for free, no receipt necessary! I broke them for good a few years later and replaced them with a pair of HD555s, bad move. I didn't like the way the 555s sounded (they were a very poor replacement for the HD540 IMO), so I tried a cheap headphone amp from fleaBay a couple of years later and still hated them. That really killed my headphone habit for a while until the HD600 and Head-fi got a hold of me. I actually replaced those HD540s recently and they still sound great even if the low end is somewhat lacking.
I stayed into music as the Walkman/portable CD player fad led to the iPod era, and got an early pair of ER-6i and PX100s driven by my Simpl A1 portable rechargeable headphone amp and first-generation iPod. I finally got myself an HD600 and the rest is history. Lossless music has replaced compressed, my vinyl is back online, and upgraditis has taken my wallet hostage seemingly for good, as I will evidently never be "finished" (but one can dream). I think (hope?) that I am approaching a major "pause" point now with headphones and surround setups, but of course I want to spend thousands on a new turntable with an MC cartridge someday and hundreds on tube-rolling, it never ends! Not that I'm complaining
The worst for now is that I am starting to realize that the majority of my old vinyl collection, while in good condition, is 1980s American vinyl, and therefore of poor fidelity for various reasons. The good ones are very good however, and replacing the bad ones with better-sounding versions is quite expensive! So it goes, but the content part of this hobby is another money hole--especially with old vinyl. Anyone want to buy a laserdisc collection?