If there were an award for the most outrageous jailbreak artist, Charles Sobhraj would definitely be nominated for his many escapes in India and abroad.
On March 16, 1986, the bikini killer, as Sobhraj was known, ordered sweets for the Tihar Jail staff on the pretext of celebrating his birthday (which is actually on April 6). He had drugged the sweets and offered them to the policemen on duty. When the security men collapsed, he simply took the keys and walked out.
Sobhraj had selected the day and time of his escape carefully. It was a Sunday and he knew there would be just skeletal staff in the afternoon, between 1300 and 1500.
He was nabbed a few weeks later by Mumbai cop Madhukar Zende at the O'Coquiero restaraunt in Goa.
Trivia: Statistics say at least one prisoner escapes every year from Tihar jail.