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Dates back to 1945, refering to how easily movie star Errol Flynn could get women into bed with him. See related Links for the real answer Hint: Its a combination of the answers listed here. "In Like Flint" was a pun, referring to the real expression "In like Flynn" (which has nothing to do with Errol Flynn--see below). James Coburn played in exactly two Derek Flint spy spoofs; "Our Man Flint" and "In Like Flint" with Lee J. Cobb.
On THE ALT.USAGE.ENGLISH FAQ FILE by Mark Israel, the phrase's first meaning is listed as "in favour, assured of success, in an enviable position." Israel goes on to state that "Some writers allege that it originated in allusion to Edward Joseph "Boss" Flynn (1892-1953), a campaign manager for the U.S. Democratic party during Franklin Delano Roosevelt's presidency. Flynn's machine was so successful at winning elections that his candidates seemed to be in office automatically." (Above text from Google Answers.) There is also a similar phrase "In like Flint", but "In Like Flynn" is the original.
The expression is "in like Flint", and it comes from the movie of the same name: In like Flint. James Coburn played superspy Derek Flint. Flint was an expert at sneaking in and getting a dangerous job done. == ==
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ViviFrom Australian-born Hollywood actor Errol Flynn, who apparently enjoyed an active sex life. So, in Australia at least, a bloke who picked up a woman easily was said to be "In like Flynn".
Another, less provocative theory is that in 1940 the Mayor of New York, Ed Flynn was such a big shot that he could get you almost anything you wanted if he liked you.
This meant he was very well connected.
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