The one that hooked me was not about the cigar at all. I smoked some fake (thought they were real at the time) Cuban Montecristo and enjoyed the camaraderie of smoking them with friends that I decided I wanted to look more into the hobby. Not sure where I went from there, but it was all downhill and fast!
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Mac Vintage #2. Got a box of 5 for about $30 back in 1990.
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My wife bought me a box of Don Tomas something-or-anothers ten years or so ago. I had been smoking drug store cigars before then. (Still enjoy Don Tomas smokes, although they no longer make my top ten list.)
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A buddy of mine brought a box of Don's to Iraq with us. He no longer smokes cigars cause the Don f*cked his world up something fierce.
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Punch Petit Punch... a birthday present from my girlfriend, which I'm sure she regrets to this day! :-)
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Fuente 8-5-8 maduro got me.
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La Gloria Cubana Wavell Maduro made in Miami, FL before CA discovered them.
I had smoked a few before, but this cigar grabbed me like no other and still does.
:-)
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Padron 3000 M was the first cigar to really grab my attention. :-)
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Padron 3000 was my attention grabbing cigar.
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First time hooked: Arturo Fuente Hemingway Churchill. First time I spent more than $1.00 on a cigar.

I took some time off and the 2nd time hooked: La Gloria Cubana Series R No.7
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It was this exact moment...Carlos Torano. This is the moment that led me to CS to find out more about this cigar, the rest is history

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Rockey Patel Vintage 1990 was the first hand made cigar I had ever had. I have been hooked ever since.
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You know, the 8-5-8 hooked me but the LGC Wavell definately set the hook! I smoked the LGC line almost exclusively for several years.

MCS
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Rocky Patel Vintage 90 hooked me. I was smoking a few things before I tried one of those and that one was the one that did it, that really got me looking for different things and wanting to learn. I still love that cigar, too.
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CAO L'anniversaire maduro c.2002. I remember smoking this and thinking WOW this is why I love cigars, I really got to smoke more:-) I've tryed some recently and they weren't the same. I heard they changed their blend:-)
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Admittedly the first cigars I smoked frequently were Macundo crystal tubos, but the one that hooked me and changed my direction was the original Oliva "O" with the band made out of material. It may have been all of the hype at the time they were introduced, but I really liked them. I still have a lot of them as well. Maybe it is time to smoke one again and see how I feel about them now.

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I was a two-sticks-a-year cigar smoker since age 18 because my pops smokes cigars, but never got on the slope. Back in December I had one (don't remember what) that made me say, "MAN! This is the first time I've REALLY enjoyed a cigar! This is GOOD!"... Then in March I was gifted a Fuente on my birthday from a friend and more-or-less repeated myself.

After that I took the plunge, bought a cutter, cheap torch lighter, a 5 stick Otterbox, and I still remember the 5 cigars I bought:

Don Pepin Garcia Vegas Cubanas
Gurkha Ancient Warrior
Arturo Fuente Chateau maduro
2x Coronado by La Flor

It was the Coronado that REALLY got me. I consider it to be the stick that ended it all for me.

Good times, good times.
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A Bolivar Royal Corona smoked in Nassau....it was all downhill from there. :-)
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My first real cigar was last July -- a Oliva Serie G robusto. It was good, and opened me up to cigars as being something I might enjoy.
Then a friend who has been smoking cigars for years gave me a La Aurora 1903 Platinum. Holy crap that was a good cigar. That's the best I've had to date and the one that started me down this slope.
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It was my first cigar since the Swisher Sweets at tent camp outs in Jr. high--A DR Cohiba sitting at Corona Cigar in Orlando on September 8, 2006. I remember thinking: I will never be the same :-)
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