Hm, I sort of pulled the trigger a little early on this thread (that's what I get for hitting ENTER instead of SHIFT). What I MEANT to write was "Best Gen Con Memory?" Since this is Gen Con's 50th year, I'm just curious to see what everyone's favorite memory from the convention is. It could be a random encounter with another attendee or maybe a roleplaying session that lasted well into the night. 

It doesn't even have to be from a recent year - it could be the very first year that you attended the convention (which would be 2007 for me).

What say you?

Since I have only been to one (last year), I don't have a lot to choose from.  But I would say playing True Dungeon the first time.

Almost didn't make it.  Was at the Hilton downtown, so walking distance, but still a good distance.  Stayed up too late the night before my 9:12am time slot.  Woke up at 8:55am.  Damn.  Sure I can make it... Running/Fast walking about 6 blocks is a really good way to get the blood pumping...

Made it to desk at 9:15 and was able to join my group.  True Dungeon was a lot of fun.  I am amazed by just how popular it is.  Well worth the time and expense.

Don't recall the year 05 maybe?

Colt cheerleaders parading through the convention parting the sea of geeks.  It was surreal.

The last two years sharing Gen Con with my son and grandson. Flying our nerd flag together was great.  We will be there for Gencon 50.

2005 is when I graduated from high school so unfortunately I was a little too busy to attend back then, but a buddy of mine in college recommended it and my school was within driving distance of the ICC so I went in 2007 and never looked back.

Honestly, my favorite memory of Gen Con is when I stepping into the ICC for the first time and saw everyone getting their badges the day before the con. I'd never been downtown prior to that (I come from a small town in Northern Indiana) and when I walked into the building from the Maryland Street entrance I was floored at how many geeks there were.

...and I use the word "geek" with the utmost respect!

I have a couple:

First was the D&D Miniatures "Grinder" event in 2005.  The Grinder is a last chance tournament to get into the Championship tournament.  I had qualified the year before, but just missed out in 2005.  Into the Grinder I went.  It was a full day event, and I ran a warband that fit my playing style perfectly, but did mesh with the current meta for the game.  I certainly got lucky on a couple of rolls, but in the end went 9-0 in the tournament which wrapped up around midnight.  The Championship started less than 8 hours after I finished!

The other was the DDM Community Draft event which I coordinated from 2005-2008.  This event was fan run, and became the largest DDM event at Gen Con (2008 had about 140 participants).  We had prizes lined up on tables about 4 tables long, all donated by participants.  Had a map design contest as part of the event as well, so everyone played on, and kept a customer map.  Though set up via grassroots efforts, it was fully supported by WotC (with some pretty cool custom prizes from them as well)It was pretty incredible!

Cracking a Darth Vader Decipher Star Wars CCG card back in... 1996 probably?  In the basement of MECCA at a Decipher run event.  It was my first Gen Con and it was a $20 card!

The surprise concert by the Violent Femmes in 1997 was probably the most memorable thing

Probably the public Rock Band game in one of the open video gaming "arcade" rooms in 2013. A guy had Rock Band set up on a projection screen, a queue on his laptop for people to request songs and/or play a roll in them, and a binder with every song listed so you could browse what was available. I got to sing "Holiday" by Green Day and "The Metal" by Tenacious D. Sadly that game setup has not returned since 2013 :(

Another one was probably the second Shadowrun Missions game I played in last year. That was one of the most fun, empowering adventures I've ever been involved in - I felt like every one of our group's characters were absolute badasses by the time we finished it. I got the killshot on the final boss (a powerful vampire mage) with a sniper rifle shot that I used my last point of Edge for. Seriously thought about cracking a one-liner beforehand ("Smile you son of a..." - an old one, but classic for a reason), but in my experience that tends to jinx the roll badly, so I decided to refrain.

It was the year after my first Gen Con...so around 2007(?)...

My first Gen Con I came alone.  I had a decent time, but didn't really get too involved with meeting others, just sort of did my own thing.  It was fine, but a bit lonely.

The next year, I showed up Tuesday and went to The Ram.  There were a bunch of gamers in the back room...at around 12-15 tables.  I randomly sat down at one and starting talking to the people there.  We've since formed our on little group. Those of us that can make it, meet up each year.  These are some great people, and I hope to keep in touch with them.  I can't imagine my Gen Con experiences had I not met up with them.  The games are great, but it's really the people that make Gen Con great.

Ducking out halfway through a 12 hour long Vampire the Masquerade game to see They Might Be Giants out on the street at the Gen Con Block Party in Milwaukee, then later getting a "Best Player" award in the mail along with a gift certificate for playing the game I left. Completely unexpected- and They Might Be Giants were pretty awesome too!

Yep, back in the Milwaukee days each game gave away a Best Player award that came with a gift certificate to spend in the dealer's hall. Might have only been $5-$10 (in mid to late 80's dollars!) but it was enough that I would wait to shop until Sunday because I usually would end up with a few of them.

Playing in the 1999 L5R tournament (War in the Heavens) was pretty fun, but I concluded it wasn't worth using up 13 hours of Gen Con for it ever again.

When the con was in Milwaukee, there was an event each year where someone had made giant Star Wars ships - I mean like a 6 foot long Star Destroyer, and everything to scale. They would then run battles with their fleets. Never played it but very cool to watch.

When the con was in Milwaukee, there was an event each year where someone had made giant Star Wars ships - I mean like a 6 foot long Star Destroyer, and everything to scale. They would then run battles with their fleets. Never played it but very cool to watch.
 

1983, Gen Con 16.
First year, went one day as a day trip, my parents dropped me and my cousin off there and we explored the Con on a $4 dollar "spectator" badge.  Spent the day seeing games I'd never even heard of and learning new games at demos in the exhibit hall.  Completely overwhelming experience - I was immersed in an environment with "my people".
I was sold on conventions and gaming ever since.