First off Mike you said "A Walk to Remember is a good movie too. Definitely not a chick flick." Dude it is so a chick flick, I cry every time I see it and it was written by Nicholas Sparks who writes books for women to boohoo over.

Ok now to my list:
Any Nightmare on Elm Street movie & Freddy vs. Jason (not the new Nightmare on Elm St b/c it was sacrilegious to remake it without Robert Englund or Wes Craven so I do not recognize it as part of the series at all!!)
Man From Snowy River (I have seen 50 or more times, never gets old)
Center Stage (I have seen at least 20 times, best song in it is remake of Higher Ground by Red Hot Chili Peppers; love it for the dancing)
Any of the Step It Up movies (especially 3 where Moose is one of the main characters, LOVE him and the dancing)

Now I am going to go really really old school on you guys:
Father Goose (Cary Grant, Leslie Caron)
Cowboy and The Lady (Gary Cooper, Merle Oberon)- This is my absolute all time favorite movie and it is from 1938. I own the vhs tape and I have seen the movie too many times to count, the theme of the movie has been reused is current movies today over and over again. Here's what it's about http://www.imdb.com/title/tt0030018/plotsummary