I'm quickly becoming addicted to this youtube channel: https://www.youtube.com/c/SoftWhiteUnderbelly/videos
This guy does interviews with skid row residents: hookers, pimps, gang members, addicts of every kind, criminals, schizophrenics, teenage runaways... the lowest of the low. (He also went through a period where he interviewed a lot of sex workers who were relatively well-adjusted (including Ron Jeremy), but I think that was more clickbait to grow the channel.) All of the stories are incredibly sad, but he finds the humanity in each of his subjects. You become invested in the stories of certain people who come back for multiple interviews: Andrea the spice addict hermaphrodite; Exotic the gorgeous streetwalker with the facial tattoos; Reilly, an old hooker with amazing stories about surviving multiple murder attempts; and Andrea, a schizophrenic crack addict. He tries to get them help but it almost never works out. Still fascinating stuff. Almost all of them came from abusive childhoods. Click a random one that looks interesting and you're almost sure to hear the saddest story you ever heard. There but for grace...