The first system you had that was "high end/audiophile", by you standards

Bose 901 IV, Kenwood integrated amp 125 WPC. SONY reel to reel & cassette deck. DBX 3-BX compressor / expander. Dyna-kit FM10 receiver. Sennheiser SD-650 headphones. 

Infinity Modulus 90 Sub sat system for music
Krell KSA 100s music amp
2x custom ordered Adcom 545 Mark II amps with white face plates to match TV
Fosgate Audionics Model III Surround preamp
Adcom music preamp (forgot the model)
Adcom 5 disc changer for my Hollywood parties
Bang and Olufsen Beolab 8000 speakers for fronts (self powered)
KEF Center channel
Velodyne ULD 15” THX sub for HT
Sony laser disc player
California Audio Labs CD player for solo listening
Bang & Olufsen white 27” TV with built in Faroudja line doubler
Matching B&O S-VHS VCR in white
Motorized B&O TV and VCR stand
B&O RL 65 rear panel speakers in white
Blue Straight Wire ICs
Monster M series 1.5 speaker cables
2x Standesign 5 tier black matte crinkle PC stands with built-in wire management and level adjusting shelves w/ spiked feet

This was my starter system. The TV and VCR started the ball rolling and the Christmas bonus paid in Sound Advice gift cards came in real handy and I had everything else in short order. I set it all up in the loft at work above my boss’ office and broke it in with a Pink Floyd The Wall and T2 laser. Shortly after, I moved into a split level 3,550 SQF lakefront house and turned the second largest bedroom into a dedicated room that also house my Pedulla MVP Signature bass and SWR Redhead. My all black ‘58 Chevy sat close by in the covered circular driveway with its competition sound system on standby and at the ready. All my material needs were covered, although I soon lusted after the Levinson 38S, I think it was? That cover shot and review in Stereophile had me hook line and sinker. I’m sure you can relate if you were around. 
 

Oooh, that intangible HIGH END… Even if it the setup was a tad uneven I’d say my first venture was back in 94 when I got my poor student mitts on a pair of Gradient Revolution dipole speakers I’d had my eyes on for a looong time. They were rather tatty after spending a fair bit of time at hi-FI shows and expos but the dealer gave me about 70% off and to me they truly were the bees knees. I remember my desire for them even outweighing the, then so iconic VR4s. I had to flip my beloved Audio Innovation 500 for a Thule IA150b just to somehow satisfy their thirst for power and ran them with a Quad CD67, Ace teacher ICs and TC8s. Few years later life took a turn and a looong period of moving, on account of education and later, jobs, between tiny apartments all over the world. Not ideal for the hobby…Still have the Gradients even if they don’t get much play time, Thule went bust and the amp died but the Quad still does service as transport. Just recently got back in to the hobby and an Italian little jewel seems dead set on sending me way deeper down the rabbit hole. The rather breathtaking little Grandinote Shinai landed in my home a few week ago. Truly an astonishing piece of kit that delivers both detail, harmonies and stomping musicality in a way I thought no integrated ever could. It’s Grandinotes entry leve amp but at €12000 I guess it actually qualifies as real “high end” even with today’s rather insane costs to stay on top of this here game.
Next step, DAC, interesting and very much not so at the same time…

I don't think it was ever thought to be state of the art, but the old Empire turntable was such a classic look.

empire 598 iii troubadour turntable - Google Search

1974/76 Paragon System E, preamp, Dyna ST70 &/or Audionics CC2, amp, big University triaxial speakers &/or Fried R4, Strathclyde TT with Luster 801 tonearm, dynavector 10?? &/or Grado Signature (middle of the 3 models). All bought used except for cartridgesLushious sound, that preamp had so much muscle, it loved the diet of Frank Zappa, Kraut Rock, Sun Ra, Prog Rock, Miles Davis, Roland Kirk, etc.