So, in the long long ago (2004), at my first Gen con, I hadn’t scheduled any events because I didn’t understand that you should do so.  I was wandering around pretty aimlessly when I found an elaborate sign that advertised for a Call of Cthulhu game.  Much like now, all the COC games in the catalog were sold out, but this one was an unofficial* game.  So I gathered my friends and showed up at the time the sign suggested.
 
This GM shows up almost out of nowhere at the appointed time, with a box full of props and characters. As he is passing out the character sheets, a group of three people come over to ask if this was a specific event.  It turns out that their COC GM was a no show and this pickup GM tells them to pull up chairs.  So here we are, at a random table with 9 players playing in my first COC game.  This GM, who’s name is lost to history, goes on to run a clinic on how to run large con games.   He gets everyone involved, controls the game, but allows for us to make our choices.  He constantly makes the witty side comments which are still sometimes used in my group of friends over a decade later.  Two Examples:  “I’ll let you roleplay that with yourself, later.”  and after a gencon staffer comes over to figure out why an unbooked game was running, “See, that was a successful fast talk”.
 
As time has passed and memories fade, I wonder if he really existed.  I have never seen him again.  Though it was not my most amazing COC experience it is up there.   

*Disclaimer: Running Unofficial games is bad, and you should register all games with GenCon.   
 

I guess I can put this here because 1) It was unexpected and 2) I haven't seen this event at all since.

Back in 2013, I was wandering around (can't remember why) and saw that in one of the video game rooms (the one with Dance Central, DDR and other such games) somebody had a big projection screen with Rock Band playing on it. Intrigued, I walked in and found an incredible setup - not only was there a projection screen, but the guy running it had a queue going on his laptop for each instrument so you could sign up ahead of time, a binder with all the available tracks so you could see what was available, and a bunch of tracks that I suspect were "unofficially" Rock Band-ized (the newest track I heard was "Thrift Shop" by Macklemore, which I know came out after Harmonix quit updating Rock Band in 2013).

Long story short, I bought some generics, paid my way in, and got to sing "Holiday" by Green Day and "The Metal" by Tenacious D. Such an unexpectedly fun time :)

Every year since, I've looked for that setup and I haven't seen it. I hope it comes back one day.

A few years back my wife joined me and we stayed at the embassy suites, which has elevators that let you see the lobby when inside.  We are a pretty average looking pair, I guess, with minimal general gaming freakiness, though we were wearing our badges.  A non-gencon couple with a young son came in the elevator with us, he looked at the lobby and said with volume only a kid can muster "Mom!!!  Look at all those weird people!!!"  His mom snuck a peak at our badges and desperately tried to shush him.  We tried not to laugh.  At that moment the elevator door opened and a very gencon guy entered, black clothes, black wide brimmed hat, black duster in middle of summer, long hair, massive beard, old briefcase with games sticking out and the kid yelled "Mom!!! Mom!!!" and the mom shushed with all she had.  My wife and I broke down.

Brief addendum: we stood behind the man in black at the line for breakfast.  He took a large plate and completely filled it with a huge stack of bacon, nothing else.  I was tempted to point and say "Mom!!! Mom!!!" but my wife would have killed me.

  One of my good Gencon memories was a game of Buffy RPG. We all really got into character, and had the tone of voice going and were just rolling with the role play. At one point a bystander asked the GM something,  and her response was essentially "I don't need to say anything, they are doing fine without me". We had hijacked the game with roleplay, and I don't think I've ever had a game like it. We did actually complete the scenario, but there were long intervals of nothing but player to player dialog.

Killer Breakfast 2010.  I made it on stage somewhat near the beginning and was given a wizard. The art looked like something from Up in Smoke, so when a pair of ghosts walked into the bar, when asked for my reaction "Hey dudes." (doing my best California hippie imitation).

Caused everyone to pause with laughter for a few seconds. Not often you can derail an event like that for a few seconds.

My worst was dealing with a DM, (1e) he ruled that the light spell was a ball of magical light that penetrated objects, meaning as the party walked down dark halls, our light went through walls and doors warning every creature we were coming.  

The weird, driving up in 85, the dark days of the interstate, I mean you would get into areas where it was easily the boonies, no traffic, no gas stations for miles, no lights from other cars or houses.  We were listening to the radio and they were talking about a bright light streaking across the sky...then there it was and then gone.  Made for a lot of conversation for a few hours.   

Marian McBrine
Event Coordinator
Gen Con LLC

BUT - I did meet Ed Greenwood that year and he got down on one knee and proposed to me. So... yeah, that's definitely one of my best GenCon memories. :)

Two years ago, a group of friends and I were walking down one of the main corridors of the ICC, when one of my friends just randomly, out of blue begins to start singing "Sister Christian" by Night Ranger.  We join in and then ... random people just join in the chorus.  There must have been 20 extra people we didn't know walking with us singing "MOTORIN!!!".   We all laughed and shook hands and went our merry ways.

That kinda sums up the spirit of the Con to me.

At my first Gen Con I experienced my first Are you a Werewolf game.  It was an adjustment getting used to the baseless accusations and reconciling the fact that many would be lynched in the name of fear. I had a great time.  My friend accused me of being a deity which then convinced the children that some how I knew what I was doing.  The last round of Werewolf included myself and 7 children.  It was surreal and also I felt like I was at work.  Gaming imitates life! 

Motorin! Watch the Price Is Right!

(I may or may not know the actual lyrics) 

Something I semi-witnessed last year as I was walking the ICC halls. I only saw the part after the shocked exclamation, but here's what I gather happened:

There was a guy walking around just like everyone else, a fairly pudgy guy with a big white beard. Another guy in a full Deadpool costume (including the mask) was walking by at that time. The guy in the Deadpool costume screams "SANTA!!!" runs up to the guy and hugs him.

Makes me laugh every time I think about it, just because it's perfectly in-character for Deadpool.

This was in the late '90s, when GenCon was in the Midwest Express Center in Milwaukee.

(Side note: The Midwest Express Center was the nicest, most attractive convention center that GenCon has ever had. It was such a breath of fresh air after the blocky, Neo-Brutalist architecture of the MECCA convention center.)

That year in the MEC, the exhibit hall was on the second floor of the convention center, and every morning a large crowd gathered in the first floor lobby, waiting for 10:00am to arrive.

Unfortunately, the escalators to the second floor had been working so hard throughout the convention that they were out of service by Saturday morning (the MEC really did have a hard time accommodating the size of GenCon), and so everyone had to climb the escalator stairs to get to the second floor.

That particular Saturday morning, there were a couple of young ladies who had been hired as models for one of the booths in the exhibit hall who walked into the MEC around 9:30am, and climbed the up escalator stairs to get to work on time, dressed in very short shorts.

With hundreds of men watching from the first floor lobby.

When they reached the top, the crowd broke out in a spontaneous round of polite applause. (This is GenCon, after all. I hesitate to think what would have happened at DragonCon.)

The ladies turned around, smiled and waved at the crowd, and went into the exhibit hall.
 

My worst Gen Con moment ended up turning into one of my best.

A few Gen Con's back, I was there for the day with two of my friends. We were walking around, waiting for the dealer room to open, when I got on the escalator. Well I stumbled while wearing open-toed sandals and tore the toenail on my big toe right off the nail bed. I'm standing there in a daze with blood all over my foot and when it dawns on me what just happened my social anxiety goes off the charts. After a quick triage in the bathroom with some paper towels, I limp down to the Paramedics station. The Paramedics were pretty cool. They bandaged me up, gave me some ibuprofen and said that they could either take me to the hospital or I could go home and see my own doctor, but either way, all anyone could do for me is give me a tetanus shot while I waited for the toenail to grow back. Not wanting to ruin the con experience for my friends (any more than I already had) and since we came to Indy in my car, I declined the ambulance trip and said I'd see my doctor when I got back to Michigan.

So, an hour later, I'm limping around the dealer room, the ibuprofen is only dulling the pain slightly, and I'm standing at a booth getting more and more depressed. The moment the thought 'why do things like this always happen to me' crossed my mind, I turned to my right and found myself face to face with a guy in a wheelchair with no legs from the knees down. For the rest of that day, the four hour drive back home, and the better part of a year that it took for that toenail to grow back, that little accident with the escalator didn't bother me one bit. Seeing that young man tooling around in his wheelchair while all I needed was a bandage and a tetanus shot was one of the greatest life lessons I've ever experienced.

Perspective on life is perhaps the greatest thing I've ever got at the Gen Con dealer room. :)

My husband and I have missed only one Gen Con since our first, in 2005.  That was 2006, the year I started law school.  2009, the year I graduated and took the Bar, was supposed to be epic.  I had signed up for a bunch of events I was super excited about, including getting a Puffing Billy ribbon, and I was planning to spend a good portion of the weekend playing Ticket to Ride.  Alas, it was not to be.  The day before we were supposed to leave for Gen Con, I threw my back out.  At that point in my life, this was something that happened to me every year or two, and usually laid me up for a couple of days (apparently it was due to deconditioning in my case, because I started taking better care of myself, and I haven't had a similar episode in years).  So I certainly wasn't going to let a little pain keep me from my vacation.  I decided to go and hope the pain would resolve with relaxation.  Well, apparently the car ride (about four hours from Michigan) aggravated my back, because by the time we got to the hotel, I was in so much pain I couldn't even help unload the car.  I wound up only going to the convention for two of the days, and the days I was there, I was at times almost crawling from the board game hall to the restroom.  I played some games of Ticket to Ride, but I would lie on my back in a corner of the hall in between rounds.  On one of the days I made it in, my husband and I were headed to one of the restaurants within a couple blocks for dinner.  As I was hobbling along, excruciatingly slowly, one of the homeless men on the corner called out, "That's it, sweetie!  You just take all the time you need.  It'll still be there."  My husband and I laugh about it now, but at the time, that little bit of encouragement, from a VERY unexpected place, really meant something to me.

The pain resolved a day or so after we got back.  I know I'm one of the lucky ones, not to be dealing with chronic pain.  But that year definitely sticks with me as one of my more surreal Gen Con experiences.

Free Dominion tournament two years ago.

Waiting for the second round to start - one game is still going one while the others were done. Woman at my round 2 table starts complaining that while she "likes that people bring kids to GenCon, a tournament probably isn't the best way to learn a game". One of the players in the game still going on was clearly a child.

That game finally finished.

The child was walking toward me to find his next game..I asked "how did it go...long game?"

"Dad I won...there were two cards that gave curses so the game took forever. How did you do?"

She didn't say much after that.

FYI - he was 12.