I love films!! Watching something 20x is quite a lot for me, though. #1 I have watched probably 10x at this point, the others are in an indeterminate 'more than once but less than 10x' category.
Vampire Hunter D: Bloodlust [2000] - incredible animation and cinematography
Sky Captain and the World of Tomorrow [2004] - retro zeerust feel and unexpectedly big ticket stars like Jude Law, Gwyneth Paltrow, Angelina Jolie and a posthumous cameo of Sir Laurence Olivier
The Iron Giant [1999] - funny and heartwarming
Kate & Leopold [2001] - my fave modern rom-com
Roman Holiday [1953] - my fave film
Disney animated films insert - Aladdin [1992], Little Mermaid [1989], Hunchback of Notre Dame [1996] and Atlantis: The Lost Empire [2001] top the list here
Other animated films insert - Anastasia [1997], Prince of Egypt [1998], Fievel Goes West [1991], FernGully: The Last Rainforest [1992] some of these were watched more than Disney but not all
The Sound of Music [1965] - family fave
Ben-Hur [1959] - papa's fave film
Remember the Titans [2000] - mama was watching this every time I turned around when I was in high school idk
Seasons of the Heart [1993] - a direct-to-video 19th century drama about a couple who adopts a little boy. Stand in for several similar family friendly Christian films from when I was growing up.
I saw Bohemian Rhapsody a couple of times at the cinema, but only because I was going with different people. Can't recall going out to see anything else multiple times.