Early, unadulterated Sierra Carche . . . magical stuff, easily 95 points.
Probably 86 Raymond Lafon or 82 Lynch Bages with my old man.
Probably something along the lines of a 1959 Leoville-Lascases.
I was in college in the 1960’s, and my girlfriend was the daughter of a VP of Shell Oil (I was at Rice in Houston TX). We’d eat with the family and they would pour some damn fine Bordeaux. I was pretty hopelessly lost after a few experiences like that…
The good thing was that wine prices were ridiculously low back then. The bad thing is that I barely had two quarters to rub together.
I was drinking wine since youth thanks to my maternal grandfather in Toulouse, but that was vin de pays plonk. The epiphany occurred in the mid-90s during a date with a hottie who worked at MTV. I can’t recall her name, but I can still taste the wine and its effect: 1992 Chateau St Jean Robert Young Chardonnay.
1982 Palmer- was working at a fine dining restaurant while studying for my MBA, as a “captain” in a dining room, knew NOTHING about wine(most would say still don’t). The restaurant sent me and one other guy to classes at Chicago Wine School. First day of class we tasted 1982 Petite Chateau’s- and as a treat they broke out a bottle of the Palmer. It was a true “WOW” moment- this was circa 1985…
1989 Hedges Red Mountain Reserve
1993 Caymus Napa
1991 Von Strasser Diamond Mountain Cab
All drank on one cold and rainy spring day awhile back…
1977 Graham Vintage Port - At a business dinner in Chicago in 1994 (Vivere).
1986 Louis Jadot Clos St. Jacques (consumed 1992)- From a changing-neighborhood liquor store on Chicago’s SouthSide. A story I need to share sometime.
Drinking a glass of 2003 Lucia Gary’s Vineyard Pinot Noir at the bar in Nepenthe, Big Sur, CA. Not the most amazing wine on the planet but the vibe and situation pulled me around the corner of the street of the wine world I had been peaking into for the year or so before. That was part of a trip that had other touch points about wine for me that only became apparent some time later.
Get out! Me too!!!
1992 OpusOne - Waiting on our table in a restaurant in Monterey CA, wondered why on the Wines by the Glass list there was one listed as $20 for a 2oz pour. Asked the bartender if that was a misprint, he said “you’ve never heard of OpusOne?” Then proceeded to explain the backstory and comp a glass for my wife and I to share. Beginning of the long slippery slope of this obsession…
I’ll also list Opus One. It was a 2001 half-bottle, I believe, ordered at a starred restaurant in SF. Snooty French somm looked at me like I had leprosy after I ordered this, but it was the first really high-end wine I’d ever had.
We were at a restaurant in Santa Monica. In those early days of my wine experience, I was smart enough to ask the som for help. This wine was a 
experience for everyone at the table. When we asked for a second bottle, they were all out.
I was up north in Napa a few months later. I went into one of those cute little stores they have up there and was able to score more.
We drank it as 1999 became 2000.
I’m glad there’s someone out there who’s more of an old fart than I am!
The first really memorable wines I had were in a wine group when I was in law school, so I was already enamored of the concept of a wine even before I had my epiphany. It was 1983 and we drank a 66 and a 69 Faiveley – I have no record of what, but probably premier crus – and they were mindblowing.
That September I spent three weeks in Europe with my law school roommate, who was also interested in wine and, more importantly, was fluent in French. We headed for Bordeaux and arranged a tour at Mouton where he spotted the retired maitre de cave roaming the premises and flattered him into letting us taste the 82. I was bitten!
Great story !
He also managed to talk Corinne Mentzelopolous at Ch. Margaux into letting us taste there, despite her initial denial of our request.
We struck out at DRC, however, notwithstanding his plea through the intercom at the front gate, “But they let us taste at Ch. Palmer, Ch. Mouton and Ch. Margaux!”
What can I say? He’s a native New Yorker.
Wish I could remember that long ago, but it was Sanford pinot noir when the epiphany came! 
-mJ
It was the wine that my wife and I had with dinner after our marriage in 1976. It was a 1971 Anheuser Riesling - I suspect either a Kabinett or Spatlese and I don’t recall the vineyard. It a huge upgrade over anything we had drunk to that point and got us started toward collecting.
My first big time purchase and endeavor into wine was 1997 Clos Du Bois Marlstone. It may actually have been a different vineyard, I remember the label was green. Can’t find a green lable anywhere, but I remember the color. Maybe someone can help.
i won’t bore y’all with the stories from trying to learn about wine while working at Sammy’s or Bellefleur… but the two wines that help start this “intellectual/metaphysical slippery slope” were the 2001 Turley Old Vine Zin and some 2001 Dr Loosen bought at a local shop in Fresno… i had the epiphany of “my god, i didn’t know wine could taste like that”
ok, i will recant a story about a former server at the Belle, who would describe a wine as “it tastes like sex”. i told my girlfriend (now wife) when we went to Turley about that server and how he would sell wine, which she promptly dismissed him as smarmy… but then she tried a Turley zin and her knees got week, and she said it “tastes like sex”
Two:
92 Hess Collection Cab started it.
95 Panther Creek Shea had me for good.