This may scratch your itch: https://www.amazon.com/Storm-Before-Beginning-Roman-Republic/dp/1610397215/ref=nodl_
He wrote a book about the beginnings of the fall of the Republic. Haven't read it myself, but I've heard good things.
Now, I have listened to the podcast, and I enjoyed it.
Though the Boomers have been a bit haughty, they're not the worst out there by any means. In the history of the US, the Trancendental and Gilded generations of the antebellum South were literal slavers. We're no where near US Civil War II.
If you look at ancient Roman history, the romans of the Marian Reform era really botched the republic. When they came into their adulthoods, all hell broke loose with Sulla and the like and their kid's generation (that of Cesar) gave up the ghost and turned to Empire. There has been a LOT said about the lumbering fall of the Roman Republic, and any form of generationalism is likely not applicable to the patricians of that age or culture. But, as THoR states, that era of 'the storm before the storm' is dripping with relations to our current era.
A good look into this further is Mike Duncan's The Storm before the Storm that leads into the Sulla era: https://www.amazon.com/Storm-Before-Beginning-Roman-Republic...
Duncan's The History of Rome podcast is very good overall and very much worth a listen.
Of some relevance is his new book that just came out, The Storm Before the Storm, which details the events that preceded the rise of Julius Caesar and paved the way for him to overthrow the republic.