Karaya's "Candy Mountain" missions, in particular the one in which we upped Kates to torpedo ground vehicles that were attacking a friendly town. I don't know what made me laugh the most, watching almost half the mission bail out mid-flight once they realized we weren't joking about attacking GVs with torpedoes, convincing the remaining that you could actually use torpedoes as bombs, or watching the chatter on 200 about the n00bs dropping torpedoes on GVs.
ack-ack
I remember that one like it was yesterday AKAK. Hearing PK1 laughing at times when I was calling out false info, was epic. I have created quite a few of them over the years with only humor being the catalyst. Whether it be:
"Running of the Bulls" - Jeep races around the center town of dweeb island. Only gv supplies were allowed to right your vehicle. Whoever did the most laps around the outside of the town won. Many a campers would simply laugh on 200 at the sight of 25+ jeeps ignoring the town and friendly gv's.
"B-17 Fighter Sweep" - This one was a Delirium and Karaya idea spurred on a tiredness of the Baltic Map one night. We upped from A43 and went NOE into A45. IIRC, about 20+ of us had gunners as well. Del was one of the few to rtb with kills, albeit in Corky fashion with oil leaks, fuel leaks and missing parts.
"Stuka Missions" - The first one saw 72 Stukas in a single mission and we decimated a town, capturing the base by accident. The second one involved the dweeb island map, 102 Stukas, completely leveling two bases, their towns and SHawk and I in tears laughing when we realized that no one rolled a goon.
"Another Baltic Moment" - Upped SBD's (since someone involved dubbed them inferior, might have been PK1) and a goon. We rolled two bases in a row with everyone flying lazily in front of enemy guns and surviving. Third base in, they finally put up some resistance and we were gladly unable to capture the base.
"Dueling 17's" - A Raptor and Karaya operation. We decided to get most of the 80th, some of SHawk's guys and Nazgul to duel in 17's down in the lower left corner of Baltic. This one might go back to about 2005 or 2006? Raptor and I augered trying to jockey for lower alt. We reupped and flew the 1/2 of an hour to duel.

"D3A's" - Hearing Floatsup whine on vox about "Great, there are 30 of you in Val's, but you cannot kill anything and we want this base. Just stay away!" About 1/2 of us landed at least 3 vulch kills when the base was captured.
Unrelated to Candy Mountain, I can only think of one moment.
"Donut Map" - I logged on to AH to find my friend Lazer pissed off that the Bish had taken all three bases in the crater. I got with Lute/RacrX and spearheaded a truce with about 100+ Rooks and 60 Knights to retake Furball Crater. It took about 4 hours, as we had to get the bases outside of the Volcano and then climb to 15k to enter the three base area. Not one Rook was felled by a Knight and vice versa. Rooks got their base first and escorted Knight goons to their town.