Mine would have to be 50 First Dates, with Adam Sandler and Drew Barrymore.
Most Helpful Guy
Con Air, Harry Potter (all of them), The Lone Ranger (Johnny Depp version), Shrek (first and second one), Spiderman (Sam Rami trilogy).1
Most Helpful Girl
I agree, 50 First Dates is a movie I watch every time I see that it's on and I never get tired of it.
Forrest Gump, Grease, My Girl, Uptown Girls are also movies that I've seen countless times and will still watch it every time it's on.1