14. Vinnie Terranova from Wiseguy (1987-1990, CBS)
Played by: Ken Wahl
Vinnie Terranova's backstory makes up for the fact that, technically, he wasn't a full-on gangster.
Terranova was tasked with infiltrating various mafia families in order to gather evidence and get the members of that crew sent to prison. To get his street cred for the job, Terranova was actually sent to prison for 18 months to gather intel on crime families and prove to them he wasn’t an undercover fuzz member.
That's one hell of a commitment, not to mention something you wouldn't do unless you’re ready to be whacked at any moment. At the same time, though, it caused a great amount of stress in Vinnie’s life. The constant pressures and lies were a running theme throughout Wiseguy, and the best part of the show was watching him twist like a hammock in the wind.
Even though he was just posing as a gangster most of the time, Vinnie Terranova was nothing less than a badass.