Blues Brother, i'm not *exactly* sure but it's either 153 or 154 times. i had the VHS (copied off TV) and used to watch half every night until the car chase to chicago, then the other half in the mroning before school. and i got to counting and telling my classmates. i also dressed like Elwood. (Elwood has white socks, Jake has black)
Next is The Rocky Horror Picture Show as when i was in college in Boston i'd go to weekly sing-along nights at the Loews theatre near harvard square. (50~ish times)
lately it's gotta be Charlie Wilson's War, i love the "my loyalty" scene SPH does in that film.
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i'm a film-nerd, there's a whole bunch of films i can recite word-per-word, lots of python, blackadder ...