8. Dr. René Belloq (Paul Freeman) in Raiders of the Lost Ark
Belloq was a scoundrel who took credit for all of Indy's exploits, but he had a certain charm to him. He would joke with Indy before trying (on multiple occasions) to have him killed. I mean, when Jones had a bazooka pointed at the Ark and is about to blow them all to kingdom come, Belloq simply replies, " Your persistence surprises even me. You're going to give mercenaries a bad name." Now that's a cool cucumber. Let's not forget how fun he was when he and Marion got all liquored up. His family owns a winery and has its own label! That's a conversation starter at parties.
7. Frank D'Amico (Mark Strong) in Kick-Ass
I absolutely loved Mark Strong's take on D'Amico. He may be a ruthless mobster, but he's also a family man who takes his son to the movies and eats breakfast with the wife. He drinks and does drugs, but not to excess and doesn't kill people when they call him out on it. He's cool with his lieutenants and is constantly joking around with them instead of ordering them around like peons. He's also rational, except for all the time. Seriously, watch Kick-Ass again and pay attention to the scenes where he's not a mob boss and tell me he's not a pleasant guy to be around.