Yes, it depends on what you are interested in but "In Search of Christian Freedom" is a must read and shows a lot of what went on behind the scenes within the GB and at bethel.
"Apocalypse Delayed" by Jim Penton is also very good (for the overall history of JWs form pre-Russell onwards whereas something like "The Gentile Times Reconsidered" is an indepth analysis of the 607/1914 chronology.
There are also others on more specific subjects or details of errors the WTS has made etc but I would recommend starting with those.