1973 Beychevelle - 5-6 years old. I remember going wacko over it.
1972 Cotes de Nuits Villages - Leroy - ditto -
1977 Sterling Cabernet Sauvignon Reserve
I was hooked.
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Circa 1984, I had a job in Pharma sales……I was mostly drinking beer and Bartles & Jaymes wine coolers at the time, when one weekend my boss had a dinner party for all the members of his district, so like maybe 12 of us. It was at his house, a much nicer place than I was living in (I was in a nice townhouse, but he lived in a “real house”, with a real “dining room”)……anyway, that night he served Kendall Jackson Chardonnay, and after drinking wine coolers, I thought it was so incredibly good! Turned out my boss was a bit of a wine lover, and from there he turned me on to many more finer wines……after that I was hooked……
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1984 Beringer Private Reserve Cabernet shared by the owner of brewpub I worked at back in 1999 or 2000.
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There wasnt any 1 for me, it was a half dozen or so bottles including:
2000 Brane Cantenac
1982 Suduiraut
2011 Bussola Amarone
2005 LdH Bosconia
Gevrey Chambertin 1er Cru from and unknown vintage and producer, wine shop has long since closed its doors 
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I partly credit a bag in a box wine (I was a student), because I got accustomed to having wine around. Pretty dreadful stuff, so I started looking for bargain bottled wine.
But, the trigger for me was less a specific wine than it was a moment sharing wine with friends on a short trip.
-Al
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While in school, I drank the usual low end juice in the 60s, Lancers, Mateus, Boones, Triple Jack, etc.
During my first weeks working in the realm of fine wine, a 1967 d’Yquem rocked my palate and my world with its three ring flavor circus.
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I already enjoyed wine, but the wine that caused the geek light bulb to go on was 1992 Arrowood Merlot.
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Boeger sauvignon blanc, sequential early 1980’s vintages, because I could afford it doing a PhD at UC-Davis.
The first wine that got me “interested” was 2009 Saviez Vineyards Cab Franc. Then the winery that really got me “hooked” was a Riesling horizontal at Forge Cellars in the finger lakes. Being able to taste how different just one varietal could be based on place was really eye opening and kick started the hobby.
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I don’t know that I had just one, but more a series of eye-openers that over time took wine from being just another drink to a growing hobby. Each of those has become a reminder of specific times in my life and left me with a fondness for those particular producers (even if I found more I loved after these sparked interest in the broader region/grape, these will always be the ‘firsts’). Though I don’t recall the vintages for most of these off the top of my head; didn’t really know until much later to pay attention to the year
When I lived in Seattle, a couple of visits to the Herbfarm left me with bugs for Oregon Pinot and German Riesling via Big Table Farm and Maximin Grunhaus. And Canlis led me to Pouilly-Fume and Barbaresco by way of Didier Dageneau and Gaja (this one I at least remember the vineyard - Sori San Lorenzo). Eden Hill introduced me to the Rocks District.
After decamping back to the Boston area, my first real wow experience with champagne came with a Bollinger Grande Annee at Le Bernardin in NY, and have been able to try some well-aged wines locally - a 1983 Guigal Hermitage at Troquet on South in Boston, and a Pontet-Canet from some mid-80’s vintage at a local wine event.
Will second @m_blasco above - I generally could have taken or left Gamay for a long time, was mostly familiar with Beaujolais Nouveau. The Foillard Cote de Py knocked my socks off.
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Dom 96 on my 11th bday got me interested in wine, and tasting the P2 version 12 years later confirmed that I made the right choice. I blame my dad for putting me on this expensive lifestyle though, especially when I can’t have wine from his cellar no more.
1982 Paul Pernot Puligny-Montrachet “Pucelles”
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Robert Mondavi use to make some Pinot Noirs in the early 1990’s out of Napa valley. There both some Reserve and Unfiltered bottlings.
1991 Phliip Togni shared with my two closest friends in 2001. I just picked up a great looking bottle and am looking forward to surprising them with a revisit almost 25 years later.
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Masi Amarone got me on the path. I couldn’t be further removed stylistically today. 
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2007 Justin “Isosceles” in 2012. Not my style of wine today, but it really grabbed my attention as someone just graduating from college.
If I were to single out one bottle, it would probably be a 2008 LdH Vina Tondonia Reserva that I had 3-4 years ago. Up until then, during my uni years, I had enjoyed wine but only in a very casual way. The Tondonia showed me how exciting wines can get with a bit of age, and that spending a little bit more on a bottle can lead to appreciably more enjoyment and complexity. Since then, I have fallen down the rabbit hole of buying wine, reading about wine, going to tastings and wine-centered vacations … and joining wine berserkers. But I am still very early in my wine journey, and I still regularly come across bottles that completely change my perspective or direction.
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Isn’t get into wine until my late-ish 30s, and the bottle that really turbocharged the pursuit (after about a year of floundering around drinking mid stuff) was a 2001 Sadie Family Columella.
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The wine bug bit me when I was at a work event with my wife and got to try a bunch of 1995 Chianti. We had very little money at that point, but I started buying a bottle of $15 wine once a week after that. I remember going to the store and spending a half hour or more figuring out what one bottle I was going to buy each week, like it was a big purchase.
That event was probably 1998, when I was in grad school.
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