Fucking lawyers - the Big Challenge

So a good friend of mine has this boomer asshole at his firm (homeboy's favorite band is Cream), and this man, so I am told, has issued a challenge. He, like so many of his enormous voting block of Beatles-loving compatriots, thinks that their generation has created the only credible music of the modern era, and he has asked me to back up my disagreement with five albums. He has promised to listen to all five, and I, or rather my good friend, would like your advice. Which albums, my dearest men, do you think embody the intrigue of our wayward generation? How can we make this man say, "I was SO wrong... how can I go on living such a lie?"