CHICAGO BY NIGHT 5TH EDITION is technically the third edition of the seminal Chicago by Night city book supplement for Vampire: The Masquerade. Way back in 1991, the book was released for the then-new series about playing tragic misunderstood creatures of the night a decade before Twilight made it uncool. The book was a shocking change the kind of books present from Dungeons and Dragons or even Call of Cthulhu. It was adult, edgy, racially diverse, sexually diverse, and full of complicated politics your player characters were meant to involve themselves in without shooting up the place. Well, yeah, they'd probably shoot up the place anyway but it wasn't advised.
THE CAMARILLA (sourcebook) is an incredibly flawed book that would have otherwise been a 4/5 if not for one incredibly ill-conceived chapter (plus many editing errors) that I think needs to be removed. But we'll get to that. Actually, no, it's probably best to get it out of the way before anything else. The Camarilla (sourcebook) contains a chapter devoted to describing Mordor meets Latveria. There's a murderously evil little country ruled by a vampire dictator which is rounding up all the gays and other innocents to be vampire snacks. Here's the problem, it's a real country. You know, you can describe Montreal as a Satan-worshiping hellhole, that's actually funny. It's considerably less funny when it's a real country.
THE ANARCH (SOURCEBOOK) is the first supplement for Vampire: The Masquerade's controversial but awesome Fifth Edition. Anarchs have always been something of the middle child of the setting due to the fact they get almost no respect from people who assume they're either part of the Camarilla but whiny poseurs or they're Sabbat-lite in that they're against the Elders but won't go to the extremes necessary to affect real change.