How is Holden Caulfield Like Jay Gatsby?

[Monty J]

They're both anti-heroes. Gatsby is a crook and Holden's a whiney rich kid who gets kicked out of school

Usually, you expect a main character to be likeable, but Salinger gets away with making Holden the opposite. It's surprising how many books he's sold by breaking that rule.

I read a lot of complaints on Goodreads that Holden is a turn-off, a whiney rich kid that can't find anything good to say about anyone. To an extent this is true, although Holden does open up about some things he does like, such as Sally Hayes's skimpy skating skirt and the way Jane Gallagher keeps all her kings on the back row and especially Phoebe's smile as she rides the carousel. Oh, and the diorama at the museum with the bare-breasted squaw.

Maybe what comes across the strongest is Holden's willingness to openly criticize what bothers him instead of "holding" it inside. Well, actually, with few exceptions, his criticisms are mostly Holden's thoughts, not outward expressions. In any event, readers who see their own flaws revealed must not like it.

Take the bone-headed jock, Stradlater, who thinks he's God's gift to women and molests a girl on a double date. Not only does Holden heroically pick a fight with him, he mentally shreds him beforehand. If I were a jerk of a jock with Stradlaterian tendencies, I'd probably not like Holden very much either.

I'm curious how many people like the book despite Holden's aggravating inner disaffection with much of his urban upper class world. Do you like him because of his honesty or in spite of it or what?

[Clara]

I've always loved Holden, he's one of my favourite characters from any book I've ever read. I like how honest he is, but mostly I like how he describes the things he liked (the ones you mentioned, but also the way he describes his brother Allie). I guess I've always liked him cause I can relate to him, to some extent. To me he's a very moving character.