The Lion King. I know most of the (English) lines now, including the jokes I was too young to get as a kid.
I also watched Frozen (2013) and The Incredibles 1 quite frequently when I was younger
Oh, I believe in yesterdayI used to watch stuff over and over again frequently when I was a kid. Not so much now, since I a. have access to far more media than the same small handful of VHS tapes; b. imagine it makes stuff "stale" if I do and mostly c. the internet now exists and I can barely drag myself away from it to watch long form content.
I think the first movie I watched as a little 'un over and over again was my aunts' copy of The Sound of Music, to the point I probably wore out the tape. This when I was about 4 or 5 and possibly developed a Precocious Crush on Julie Andrews, which stood me in good stead to watch Mary Poppins as well. I'd probably rewatch quite a bit of the Disney canon as well; an odd one perhaps being Fantasia- I loved classical music back then!
I was also into space, and it wasn't too long before my elders introduced me to sci-fi stuff... beginning with Star Wars. A couple of years later, Star Trek IV: The Voyage Home was my introduction to Trek, and probably still remains my favourite of the TOS movies.
Other slightly later favourites were the Back to the Future movies, and I'm sure hearing Huey Lewis and the News kicked off my teenage '80s pop obsession, in which I would scour charity shops for old vinyl, all way before it was cool. (Seriously, being a teen in the late '90s/early '00s obsessed by retro stuff was certainly something to get you made fun of... typical it only becomes cool years later!)
I literally had a different Disney movie for each day of the week. Can't remember the exact positions, but they were Pinocchio, Lady and the Tramp, 101 Dalmatians, The Aristocats, Robin Hood, Mary Poppins and The Sword in the Stone.
A lot of them... But I think Frozen (2013) comes first...
Life is not easy, but that’s why we stick together.Used to watch Open Season, Surf's Up and Barnyard religiously
When darkness meets the light, this is what it sounds like!

Come to think of it, I think I remember seeing Up a number of times when I was younger, given that it first came out when I was about 5.
Cold turkey's getting stale. Tonight I'm eating crow.