To be in like Flynn is a fairly new idiom, only existing since only the mid-1900s. Flynn is a proper name, and this expression is one of hundreds of proper-name idioms, most of which don’t survive for nearly as long as this one.
It is hard to say why this particular idiom is still in use while so many other proper-name idioms have long vanished, only to survive in old films and newspapers. It could be the rhyme.
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Meaning of In Like Flynn
To be in like Flynn means to be very successful, but with a connotation of taking great advantage of opportunity, being “in’ with the right people, and having your success assured. It can also refer to sexual success or to both professional and sexual success.

Example Of Use
When Sue came out of the board room, she didn’t show a hint of emotion. Did she get the promotion or not, wondered Terrence. “So, did you get it,” he asked.
“I’m in like Flynn,” she replied, with a sly grin.
Origin
This idiom refers to a real person, but there are two claims to the identity of that person. One claim is that it refers to Errol Flynn (1909-59). Flynn was an Australian-born actor who was very famous for playing swashbucklers and playboys in Hollywood films. He was also notorious for his private life of heavy drinking and many sexual encounters. Flynn himself refers to the phrase in his autobiography, My Wicked, Wicked Ways: The Autobiography of Errol Flynn:
“…crowds thronged into the theaters to see my pictures and get a double laugh…at the film fare and to enjoy seeing the man who gave them so much entertainment over and beyond the call of picture-making. A new legend was born, and new terms went into the national idiom…A GI or Marine or sailor went out at night sparking and the next day he reported to his cronies who asked him how he made out, and the fellow said, with a sly grin, “I’m in like Flynn.”” 1
Obviously, Errol Flynn himself thought the idiom referred to him. The other claim, however, favored by Americans, is that the idiom refers to Edward J. “Boss” Flynn, a 1940’s Democratic Party activist who was the campaign manager for Franklin Delano Roosevelt and others. He seemed to win elections without breaking a sweat, to the extent that his candidate was an automatic win. So, his candidates were “in like Flynn” himself.
The passage above refers to Flynn’s 1942-43 Statutory rape trial, where he was acquitted, thought to be the origin of the phrase’s association with Flynn. The first written evidence of this is from 1945, in American Speech, where “in like Flynn” is said to be U.S. Air Force lingo for “A-OK,” supposedly referring to Errol Flynn. However, there were earlier examples of the expression found by etymologist Barry Popik of the American Dialect Society. He found an example from 1940, and another from the San Francisco Examiner sports Section, in 1942:
‘Answer these questions correctly and your name is Flynn, meaning you’re in, provided you have two left feet and the written consent of your parents.’
He also found evidence in a 1943 newspaper that the phrase might sometimes be shortened to “I’m Flynn” to basically mean I’m in.
This timeline might suggest that the phrase was at first connected to Edward Flynn and then was transferred to Errol Flynn when he became so infamous. However, in truth, there is no strong evidence of its connection to either man. We really do not know for sure how the phrase originated. Some suppose that it had nothing to do with a real person and was just used because of the rhyme.
In 1967, a movie starring James Coburn spoofed the expression. A sequel to the spy-spoof, Our Man Flint from 1966, In Like Flint caused many people to think this was the original expression. See movies with idioms for titles. 2,3
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References- Flynn, Errol. My Wicked, Wicked Ways: The Autobiography of Errol Flynn. London: Aurum, 2005.
- Allen, R. E. Allen’s Dictionary of English Phrases. London: Penguin, 2006.
- Wilton, David. Word Myths: Debunking Linguistic Urban Legends. New York: Oxford UP, 2004.