Judy Garland and Mark Herron with the infamous Kray Twins.
Reginald and Ronnie Kray were the kings of underworld crime in the UK during the 50's and 60's.
Here is their blurb from Wikipedia:
Reginald "Reggie" Kray (24 October 1933 – 1 October 2000) and his twin brother Ronald "Ronnie" Kray (24 October 1933 – 17 March 1995) were the foremost perpetrators of organised crime in London's East End during the 1950s and 1960s. Ronald, commonly referred to as Ron or Ronnie, most likely suffered from paranoid schizophrenia.[4] The Krays were involved in armed robberies, arson, protection rackets, violent assaults including torture and the murders of Jack "The Hat" McVitie and George Cornell. As West End nightclub owners, they mixed with prominent entertainers including Diana Dors, Frank Sinatra, Judy Garland and politicians. The Krays were highly feared within their social environment, and in the 1960s they became celebrities in their own right, being photographed by David Bailey and interviewed on television. They were arrested on 9 May 1968 and convicted in 1969 by the efforts of a squad of detectives led by Detective Superintendent Leonard "Nipper" Read, and were both sentenced to life imprisonment.
Ronnie remained in Broadmoor Hospital until his death on 17 March 1995, but Reggie was released from prison on compassionate grounds in August 2000, eight weeks before his death in October from cancer.
The Krays were not the first criminals Judy associated with (nevermind that she was managed by a few), as far back as when she was a little girl she was known to have no fear in approaching or partying with the world's "bad boys."
Here she recounts approaching John Dillinger for his autograph mere moments before he was shot and killed:
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