• 1974, age 60
Even if you got past the guards, Alcatraz was supposedly inescapable because of the treacherous swim to the mainland. But at 60 years old, LaLanne did it, handcuffed, shackled, and with a 1,000-pound boat tied to a belt around his waste. To guard him from sharks, police followed him in a boat. LeLanne later said that the police officers had spotted two sharks just 20 feet away from where he was swimming.