Oh yeah, I did this with one guy. I played him for about half an hour just making stuff up - I wasn't at my computer at all - and then I turned on him and asked him how he slept at night and what his mother would think if she knew how he spent his days stealing from little old ladies, etc.
He did not like that. Hung up on me and then, still enraged I guess, rang me back and tried to have a go (which didn't work, naturally). I hope what I said got to him.