Craziest ever was a campaign where I was playing a hobgoblin “Mad Chef” character. It was a house-made prestige class that was basically a rogue prestige, that used a greataxe as a “giant cleaver”, and had a 1/day ability called Flambé that would make the cleaver Flaming Burst.
So my character was in his "kitchen" at our fort, while the rest of the party was screwing around with a magic bell that summoned random monsters. They summoned a few weak things, then got a Purple Worm, who started wasting them. My guy runs out, cleaver in hand, and surveys the scene.
This was in 3.0, where rogues could use a feat called...Expert Tactician I think? It allowed a free attack whenever an opponent was denied his Dex mod (and since he was denied Dex, was a free SNEAK attack). Combined with Improved Feint, it was a good combo.
I asked if I could feint the Purple Worm, hoping for the free sneak attack. The DM ruled that since the Worm was deaf, I couldn’t “feint” it in a traditional sense. So I asked if I could jump up and down and thump the ground to feint it instead. He said yes, but it would provoke an attack. The rest of the party was either wounded or dying, this was the do or die moment. I went for it.
The provoked attack hit and the DM started rolling the swallow-whole roll, while the other players groaned. But one massive strength check later, and my chef THREW OFF the purple worm (an epic feat already!) and took his attack. Natural 20. I look at the DM and tell him I activate my Flambé ability. Crit confirmation roll...natural 20. DM looks nervous, and the entire table is speechless and watching the next roll. A third natural 20, followed by a 17 or something (a hit). So a triple crit, with sneak attack, and flaming burst. Killed the worm in one attack.
In-game, my chef cleans his axe on the ground, looks around at the scattered, wounded party members (none actually dying at this point), and without saying a word, brushes off his hands and walks back into his kitchen.