I remember playing a game with my friend as a kid. I think it was around windows 95. You were a Mafioso and you could pick one of three businesses, one was a blow up doll factory. You had to plan heists by buying escape vehicles, such as tandem bikes, cars anong other things. I found it funny that only 2 people could escape in a transporter, because it had only 2 seats. The main goal i think was to steal from the comically large vault of the main mafia boss via submarine. My memory is very hazy, don't remember the name or anything else, but it was super fun.