I think it's hard to imagine yourself being someone else, because if you had his/her character it wouldn't be you anymore, but if you stayed yourself it wouldn't be the gangster anymore...

if this all doesn't count, I would say a "funny guy" like Tommy D (Pesci in Goodfellas) would be cool...

oh and of course Frederico Corleone ("banging Cocktaill waitresses 2 at the time)

btw, Buikie, welcome to the board! another Dutchie, our groupe is getting influential!