10 Stupidly Risky Plans From TV's Most Notorious Villains

4. Phil Tries To Whack Tony - The Sopranos

If viewers learned one thing throughout the television masterclass that is the Sopranos, it€™s that you can€™t kill Tony no matter how hard you try. The amount of attempts on his life make them an almost everyday occurrence, and the closest he ever gets to meeting the reaper is when he is mistakenly shot by his senile uncle. It€™s a sorry state of affairs when a confused pensioner is the most effective hitman in New Jersey. Apparently not learning anything from Tony€™s infinite supply of luck, the final season of the show builds to its climax when rival boss Phil Leotardo decides to wipe out the entire Soprano crime family. At first his plan seems to have a lot going for it: Tony has plenty of enemies, and New York certainly has more muscle at its disposal. The caveat is that it hinges on a tight timeframe and perfect execution. Spoiler alert, it doesn't work out. While most of the top tier Soprano mobsters are hit successfully, the most important target eludes the attempt on his life (again). Far from Phil's plan having a contingency, the simple fact that Tony is alive is enough to make the majority of his lieutenants turn on him in exchange for their lives, forcing Leotardo into hiding and eventually under the wheels of an SUV. All-out war is always a gamble, but when you declare it against an opponent as vengeful and death-proof as Tony Soprano, the risk ends up outweighing the reward.