My rogues tend to make people regret playing with me.
I was playing a pirate (rogue/bard/fighter, bard for sea chanty + glibness) and since it was the first game, the DM was being especially generous in "party-meshing" circumstances. I spent the first session doing everything possible, caught or not, to rob the entire party, aside from the barbarian, if only 'cause she was the only person there who'd hit me in real life.
Wound up, I ditched them with an inn bill, hoofed it to the market, disguised myself as the medieval equivalent of a bag lady, and still somehow managed to get caught, only to pull off some sleight of hand and cheat them again.
The entire campaign was spent making sure I got "boat funds" to take care of our "boat" that we basically stole, that didn't actually need maintenance, along with making sure to steal everything that wasn't nailed down. I had about four times as much gold as any character, roughly 50% of the entire party's wealth. (4-5 regular players)
Aside from that the character was completely combat ineffective and spent his time doing flips and sea chantys and other bitchin' feats, like swinging off chandeliers, riding flaming bedrolls into seas of zombies, and generally just the coolest thing I could imagine someone with +20 tumble/balance/etc. doing.
Oh, and he had three fake names, each one being an identity to another, so that it worked out to layers of lies, etc.