At exactly what point did Boomer live up to his name and turn into an old white man?

Really, he's becoming more and more insufferable with all the snide political takes that he's now shoehorning into everything. He's now that old out of touch curmudgeon that rants about his time and the good ol' days while shaking his fist in the air. It's sad too, because when he was younger he seemed so cool.