Reggie Kray
Criminal
One half of the notorious Kray Twins, who ran a criminal enterprise in London in the 1950s and 1960s with their gang The Firm. They were hugely influential during that time, simultaneously owning popular nightclubs and becoming celebrities in their own right.
He was a successful amateur boxer before being conscripted into the army, which he and his brother promptly deserted. They then spent time in military prison, where their behavior was so bad that they both received dishonorable discharges.
In 1967, he murdered gang associate Jack McVitie, stabbing him to death after his gun failed to fire. This murder ultimately led to the arrest and conviction that put both twins away for life.
He was born ten minutes earlier than twin brother Ronnie and had an older brother named Charlie. In 1997, while still in prison, he married Roberta Jones. He received a compassionate release from prison in 2000 and died two months later from cancer.
They reached such heights in the 1960s that they mingled with the likes of Frank Sinatra.