This is bad.  My memories are all jumbled up.

Either in 1990 - the first year I won the Nascrag tournament, or 2005, the first year I was the author.  All Nascrag related, of course.  Nascrag is always my tentpole.

Having only gone the last 6 years, 2014 was a highlight.  Only time I've been able to go all 4 days & get a downtown room.  Played Tower of Gygax charity event - pay a $2 generic ticket to  play 1st Ed D&D until your character dies (then get back in line if you want).  1st night played with a group of other oldtimers who played D&D in the early 80's (like me).  Next night my son and I played together.  One of the best DMs I have ever played under.  Playing Toon Expedition to the Barrier Peaks and the charity auction were highlights last year.

2014 was my favorite, because my way of seeing the Con changed. It was my 4th time coming, but my first time staying downtown. I don't really remember any games specifically, but just being a part of the atmosphere every waking hour made me really love the event more than I already did. Our group also grew from 3 to 7 so there were even more friends to have a great time with.

Watching Auctioneer Josh take the $10 voice changer gadget I put in the Auction and improv hilarious things to say with the various voices, to increasingly excited laughing bidders, until it ended up selling for almost $70.

That pretty much covers everything I love about the Auction, which has been my favorite part of Gen-Con.

At least since it stopped being my least favorite part.

As in, when I used to wander into the room once per convention, hear people selling multiple copies of 1950s horseracing board games, and think "this has to be the most boring event in the history of the world."  Though now even 1950s horseracing board games are fun to me because I think back to how wrong I was about the Auction generally.

I would have to say my first GenCon.  It is largely a blur, but it was such a great blur!  I got mixed up with the crazies over at NASCRAG and ended up playing with them for 16 hours.  It was a last minute, totally on a whim thing that ended up being SO much fun!

Last year I actually got to go to the opening ceremonies for the first time.  That was pretty awesome.  I love those moments where I can look over the sea of humanity and realize that all some-odd-thousand of us are there for the same reason.  It's sappy, but so what.

This year I'm looking forward to playing as much Shadowrun as I can manage, so I'm sure that will make for many many more great memories!

My group went for the first time to GenCon 2016, for a friend's bachelor party.  That was a lot of fun in and of itself, and we're definitely coming back this year, but one game in particular stands out - playing GameWick Games' Shuffling Horror: Pittsburgh '68 with one of the guys running the booth.  We had a blast, and even though it was entirely unplanned and was just a use of generic tickets, that's the game I remember the best.  We're definitely going to try to hunt him down again this year.

My best memory of GenCon was our first year back in 2004. My daughters reactions when we got to the airport and saw that we had a limo ready to take us to GenCon was priceless. They were so excited and then the next day came and the Dealer hall opened, I think my jaw hit the floor that year. We did not sign up for any events, just walked the dealer hall for 4 days and it was Awesome!
 

I am excited to hear that someone has done the legendary "just hang out in the dealer hall for 4 days."  Some people talk about how you do not really need to go through more than a couple of times, or once a day at most, but I know I have never gotten sick of going in there even after walking the whole thing twice a day all four days.  Though the more things you are interested in buying, the more interesting it obviously is--being a dumb kid who really, really wanted to own a single stupidly-expensive Magic: the Gathering card definitely kept me occupied for a full day in 1997, haha.

'03 through '08 for me.  So much awesome.  

I lucked out rooming with BYOV my first go, when they stole the cheese.

Great parties and game sessions, friends I still have today...

Taken my family since, and watched our daughter take down Cardhalla tower down with first throw a few years ago....

The game itself was called Capital Ship Combat.  8 hour event and very hard to get into.  Had the pleasure of playing in the very last one they ever ran at Gen Con.  Was so much fun to play and the ships were awesome.

Been to the Con 11 years running at this point. Over the last 5 years it has been a great time to bring my son to the con. Just a few months after being born he was being walked around the exhibit hall in a Captain America outfit. Last year was amazing as I got to meet Eric Lang and Bruno Faidutti on just a random encounter. Every year of the con holds new and amazing experiences.  

Hmm, been attending since 1984 without a miss, so tough question. so many good years. I have very fond memories of that first in 84 Parkside, There was one in 92(I think) at the old MECCA Center, Milwaukee, which was an overall awesome year, capped by fireworks we watched from the Mecca to Arena Skywalk. Then 2015 , after a particularly awesome PF event, Playing Drunken Dwarves game at Scottie's, then moving along to a couple other places, much encouraged by the awesome bar staff at all places. Can I pick 3? :-)

I have two and they both involve my daughter.

I have posted this before, but my daughter was about 8 years old and looking at some giant foam dice in the dealer hall.  She went to buy them only to find out the the gamer in front of us bought them for he.  I think he was amused at her total excitement to get these dice.

Also, last year when my daughter cosplayed as Rey (with an awesome costume if I must say) and there was a really nice guy cosplaying as Finn and he totally accepted her hanging out by him in the cosplay area.  The way the adults in the cosplay area were so nice to her made me so happy!

2003, which was the first time I attended.  I had gotten it into my head about a year prior that I wanted to attend a convention.  Me, my brother, and 2 cousins all pooled our money and attended.  It was fun to get out there and try a convention for the first time.  It was also the first road trip I had ever taken the lead on.  We took annual road trips to see relatives in Chicago when I was a kid, but my father was always Captain of those voyages.

We got a great price on a hotel a block away from the convention center.  We got to meet our heroes at KenzerCo.  The other three all got called up for the KODT Live Reading, and my younger cousin even got his picture in KODT.

I went again the next year, but somehow it just wasn't as fun.

This year I'm finally going again for the first time since 2004.  Since I moved to Indianapolis for work this past October, going to Gencon now feels almost mandatory.

Oh man... so many.  Initially I'd say my second GenCon, where I organized the Battle of Milwaukee  for 7th Sea: CCG. 

But, then I think on it more, and Honestly, I'd have to say the first year my team switched from 7PM - 1AM NASCRAG to the earlier time slot.  We went from sort of kind of solving the puzzles to doing well (we made the second round, and I was an alternate for the third -- didn't get to play though, since everyone showed up for the third).  Something clicked that year, and something witty and clever started being more awake and better [largely due to us doing well enough to take it "seriously" and do it in the early timeslot], and since then we've just been steadily climbing the ranks!  Not much farther for us to go, but there's a few spots left to take over :P.