I guess my grand father on my mothers side would be the most "interesting" one... his piece of shit father left the family so his mother had to raise 5 kids on her own. My grandfather being the oldest son had to work from very young to help the family out.
Later in life he had a sucessful business and for what Ive heard he made a lot of money but he wasted it all on friendships, partying and trying to show off. He was already married so I give a lot of props to my grandmother for not leaving his ass out, for what Ive heard my grandmother was always very supportive of him and "let him be" even when Im sure she suffered a lot from his lifestyle.
He was a drunk for many years of his life and had a lot of demons. I always thought that he never had a great relationship with my grandmother because of his lifestyle but not too long ago on a personal conversation with my youngest aunt (his youngest daughter who is now in her 60s) I discovered that after his business went down and he calmed down he went back home, reconnected with my grandmother and had a great relationship the latest years of his life.
My youngest aunt who was the only sibling left at the house lived with them through those years and she told me my grandmother on weekdays during lunch used to urge her to find the station on their old radio so they could wait for her dad (my grandfather) and the 3 of them could have lunch listening to their favorite soap opera on the radio. This is the most beautiful memory my aunt could have shared with me and this will be the image I will take with me of my grandfather, a wild intelligent crazy man who made mistakes but finally found his way back home with his loyal wife and his youngest daughter and they could sit down, have lunch and listen to the radio. RIP Jose Aspillaga