The closest I ever came was a campaign called "Second Born."
Each of us made a spoiled Tir Tairngire noble's brat, late teens to early twenties, who started the campaign sitting together at the lesser sibling table at some Tir holiday. We wiled away an evening with brandy, wine, flirting, and rumormongering about one another, until the wager was made; we each had one week to prepare and to work out the details of how much wealth we were allowed to leave Portland with...and then we'd all sneak off to Seattle (however we could get there) and live for six months as one of those dashing "Shadowrunner" blackguards from all the tridshows. Whoever came back with the most money (or equivalent, foci, telesma, etc, all counted) at the end of six months won.
We were a foppish ensemble of druggies, perverts, jaded cynics and idealistic (racist) Paladin wannabes, a few bemused mages, an adept...ah good times, good times. I wish the game had lasted longer.
