Interesting question, I've been thinking long and the first thing that comes to mind is Casino (1998) starring Alex Fong. Thanks to this movie, I fell in love with the gambling world and have been playing at Bizzo Casino https://bizzo-casino.co.com/ for over a year now! After this question, I even added this movie to my watch list because I had forgotten about it

Not sure but might have been the movie version of death note

Switched or Good Morning Call (both jdramas)

the first movie was probably Ao Haru Ride 2014

Waterboys