The alt.usage.english FAQ   

• "in like Flynn"

  (Phrase Origins)
  
  

  
     This phrase's first meaning was "in favour, assured of success,
  in an enviable position".  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.
  
     But the phrase was popularized with reference to Australian-born
  Hollywood actor Errol Flynn (1909-59), whose amorous exploits gave
  it a second meaning:  "being a quick seducer".  The earliest
  citation we have seen does refer to Errol Flynn (but not to
  seduction):  "_In like Flynn._  Everything is O.K.  In other words,
  the pilot is having no more trouble than Errol Flynn has in his
  cinematic feats." (1945 in _American Speech_ Dec. 1946, 310)
  
     The phrase "In Like Flint" has also been heard: it was the title
  of a 1967 movie, a sequel to "Our Man Flint" (1965).  Both films
  were spy spoofs starring James Coburn.  The 1967 title was, of
  course, wordplay on "in like Flynn" and the character name "Flint".

  
  
  Source: [Mark Israel, 'Phrase Origins: "in like Flynn"', The alt.usage.english FAQ file,(line 4999), (29 Sept 1997)]
  
  
  
  

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