MS Solitaire, Space Pinball, and Minesweeper come to mind. They were not my favorites, but I know a few people who have a few hundred hours on one or more of those.
For me it’s C&C Generals Zero Hour. I have had a copy since it released in 2003, it still works, and I still play it in single player mode at least once a week. It’s great because it does not require a huge time commitment and campaign missions take about an hour or less to complete. To me it’s one of the best RTS style games out there. My second favorite? C&C Red Alert 2 and Yuri’s Revenge.
I have also very much enjoyed the Assassin’s Creed series up to AC Odyssey.
I had a cat who did this. I loved it and was a bit disappointed when he stopped a few weeks later.
You said he is young. He will likely calm down as he gets older.
If the crying really bothers you, pick up the bowl as soon as he stops eating and don’t put it down again until the next meal. Then there will be fewer clues when it is time for food. He will still know, but it will require more effort on his part.