This is a tough one, but I figure Ill give it a try...

First, a cedar tubed Davidoff Anniversario #1
This cigar got me started on fine hand-rolled cigars at a young age. I still remember smoking it and experiencing the smorgasboard of flavors.

Second, an ERDM Lonsdale (Havana)
Not my first, but a most memorable cigar that was smoked with friends after a dinner at D1tkas and a walk downtown in the fall several years ago

Third, CoRo - described in prior threads

Of course, this list is subject to change!
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My list is far less exquisite than most already posted, but it is mine nonetheless.

#1 Davidoff Diademas Finas 100 Anni
#2 Padron Anni 1926
#3 Illusione 88

:-)
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It looks pretty exquisite to me. :-)
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Padron Anniversario Maduro 1926 - 40 Year, no explanation needed
Opus X - Forbidden X from 2004, no explanation need either...
La Flor Domincana Double Ligero - nearly the entire line excluding special editions/releases, simply because of the price point and consistency.
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Wow, you know I really don't know that I can answer that one. I usually smoke alone and my best friend (whom I introduced to cigars) is extremely new to all this so we don't get to smoke as often as I would like.

I can narrow it down to Padron, Fuente Curly Head? (Maybe) uhm and Certainly a Taboo twist or camaroon. It's hard to remember to be perfectly honest.
Cheers,
Rob
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Not an easy choice, but here are mine as of today:

Padron 1926 #9 Natural
Tatuaje Reserva J 21
H. Upmann Magnum 50
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Tough question, but I'd have to say
'03 H Upman Sir Winston
RA Eminencia
RA Belicoso Fino
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Tough one...
Ramon Allones RASS 03 (first exotic stick)
Padron 80th (Birthday smoke this past november)
Cohiba Limitada (the year escapes me 03 I think, I am at work and cant remeber)
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I’ve smoked many good cigars over the years and I find that the ones that I have enjoyed the most were with close family and friends. There’s something about the experience that can turn an everyday cigar into something great! Some that pop into my mind are ’98 Fundy, ’01 CoRo and ’02 MC2.
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70s Partagas Presidente (awesome ppp, thanks to Eric and Mark)
06 Monte 2 (damn I wish i still had that box)
90's something, i forgot, Cohiba Siglo II (thanks Mark)
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AF Anejo #77 Shark
Sitting in the driver's seat of my van in the hospital parking lot after I had just found out my wife's total hysterectomy went successfully.

Camacho Triple Maduro 6x60
Went on a one-day road trip with my children through central Florida in search of the perfect boiled peanuts. Then we went to my parents' home and dropped off some of our discoveries and let teh babies play with my parents' collection of mini-lions, I mean house cats.

One of the greatest days of my life.

La Gloria cubana Serie R #6
The last Christmas party with 3 fellas I worked with for many years before I moved away. It was a cool December night, we were sitting on a beachside wooden deck drinking awesome LI teas and the 6's were perfection.
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hmmm for me
monte 2- 2002- had this year, it was great
pardon 1926 torp-80 years ann

#1- was a gift from a former head of quality control at the partagas factory in havana cuba...i was fortunatly able to stay at his B&B on my last years visit...sorry no pics
it was un banded....it was sr. corona size, and was from the 70's....it was buy far the best i ever had.
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1. 1984 Dunhill Estupendo (Thanks VirtualSmitty!!!!)
2. 1950's King Edward (Clear Havana)
3. 2007 Davidoff Diadema Fina (Thanks Papajohn!!!)
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1. Oliva V Double Robusto
2. 2003 Sir Winston
3. Oliva Special S Corona or Oliva Masterworks 2 Robusto.
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For the cigars themselves:

Dunhill Mojito - These, to me, are what cigars should taste like. Just perfect in every way.
1492 - It's unique. Can't really describe it. Nothing else like it. (thanks, Dave)
Don Candido 502 - So strong after so long. Dunhill flavor on steroids. Couldn't smoke these all the time. But boy are they amazing.

--
Every cigar I smoke with a friend is a great one.
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05 Cohiba Robusto - I got them january 07, they were "on" then and fantastic, doesn't hurt that my wife surprised me with them (and that she listened when I told her where to buy)

07 Boli PC - first cigar after months of not smoking, perfect creamy spicy flavor

Conch Republic (key west) Hemingway - got it on my honeymoon while in key west, it was delicious, and was the stick that got the ball rolling for me
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Just for the cigars, not cigars + circumstances.

1) 03 Jose Cueto Salamones-Nubbed at the first Chico herf with tzaddi
2) Original release Edmundo Dantes Conde 109
3) Cohiba Sublime shared in a PPP at Ratters
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1492
1994

Number 3 is a bit more of a challenge. Either the Dunhill Malecones, original release (1987) LFDC Coronas, Partagas 150th Robustos, Partagas Dunhill Sel. 150, R&J Clemenceau). Really a tough choice. But, 1492 is the clear winner and 1994 is a clear #2.
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Just the cigar alone would have to be

PSP2 Tubo 2008
Partagas Presidente 2002 as best as I can remember
Camacho Scorpion
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1. Padron 2000
2. Padron 2000
3. tie: Cusano 18 paired maduro/Padron 2000
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