Somewhere in the halcyon years of internet writing, I read — or, at least, I remember reading — a piece titled “Holden Caulfield was the first millennial dipsh*t.” I’m almost positive this piece existed, and the fact that I couldn’t find any mention of it in the sad, hollowed-out husk of the 2026 internet offers no proof that it didn’t. What did turn up are a newer generation’s takes on Holden, many of them unexpectedly harsh: He’s “the most insufferable character ever written,” “an entitled brat,” the “original ‘needs to touch grass’ guy,” a “clueless rich kid who’s never had to try,” a “self-important, spoiled and worthless little sh*t,” and “an emo narcissist with an inflated sense of his own self-worth.”
Millennials were the first generation to anoint old Holden as “problematic” — a 2009 New York Times piece titled “Get a life, Holden Caulfield,” quoted educators who still taught “The Catcher in the Rye,” a book that turns 75 this year, and was once a standard in the English curriculum for grades 9–11. One educator said that, when she taught at a public charter school, “I had a lot of students comment, ‘I can’t really feel bad for this rich kid with a weekend free in New York City.’” A teacher who taught the book over 3 decades noted that “Holden’s passivity is especially galling and perplexing to many present-day students . . . “[T]hey do not have much sympathy for alienated antiheroes.” And one recalled a boy telling her, “We just wanted to tell him, ‘Shut up and take your Prozac.’”
