"The Iceman" is the nickname of Richard Kuklinski, a Mafia hit-man who claims to have killed over 200 men, and among other things is crossed between very badass and very creepy.
Born in 1935 to Polish and Irish immigrants, he was known as The Polack because of his Polish heritage. However he soon became The Iceman after fellow gangsters became aware that he put his victims in industrial size freezers to disguise the time of death.
Not Pictured: 6'5", 300 lb hit man
His relations with organized crime began after a bad experience with a loan shark. The loan shark, Roy DeMeo, recruited Kuklinski into their band of merry men, and quite unlike Robin Hood, Iceman started selling pirated porn. Eventually Iceman moved up to the mighty position of gang enforcer; however this job required a prerequisite test. As Kuklinski claims, he was sitting in DeMeo's car when DeMeo pointed out a random passerby, a man walking his dog, Iceman got out of the car and shot the man in the back of the head. Needless to say, he was now the gang's top hit man.
As a contract killer who's killed 200 men, it's very likely Iceman was getting tired of using the same methods each time, so he bought a crossbow. Now he wasn't overly familiar with a crossbow's power, so he wanted to test it out. He was driving in his car [with crossbow] when he pulled over and asked a man for directions; he shot the man in the face. The good samaritan who had a crossbow bolt sticking halfway into his skull, was now dead as Conan O'Brien's contract with NBC. Iceman drove away contented, knowing he had a nice new toy and sweet story to tell his kids. Except, Iceman's family and neighbors had not a fucking clue he was doing crossbow drivebys instead of filing tax returns.