A lot of my favorites from when I was younger were very reactionary and misogynistic on second reading. Esp. Richard Powers (his book for mega-fans 'Galatea 2.0' is auto-fiction about stalking a grad student), the freak who wrote 'The Water Knife', and Neil Stephenson. Lots of very gross portrayals of women and gratuitous sexual violence.
I've been meaning to read 'Educating to Govern' by Detroit Communist Grace Lee Boggs. Also 'Teaching in the Regio Emilia Way' is in the same vein of child-directed learning as Montessori and Waldorf without the eco-fascist associations. It was developed in the heartland of the Communist Party of Italy during their strongest period and was a real innovation in progressive, child-centered education.
Summerhill: a Radical Approach to Childrearing is a charming example of the last vestiges of pre-Marxist utopian socialism applied to the context of the British boarding school. Not too too much to be learned or applied for most urban contemporary teachers but it is a beautiful encapsulation of an experiment.