I'm not seeing what points readers to Hotchkiss in popular culture. Please clarify.

If the section is called "Hotchkiss in Print" then maybe movie references are not appropriate here, or the section should be renamed.

As to your point about "disgruntled alums:" Whether the quotations are positive or negative is immaterial. If they are references in print and they shed light on the history and reputation of the school, then the quotations seem entirely appropriate here. Would we want to include every last mention of Hotchkiss in the written record? Perhaps not. However, below are reasons for including quotes I have recently added (actually, re-added because they were removed at some point).

Thomas Hoving quotation: Hoving is one of the more notable alums, a longtime director of the Metropolitan Museum of Art. As a public figure who is also an alum, his perspective on the school is significant. McPhee is also a leading writer of profiles and this piece originally appeared in the New Yorker. So, it's authoritative.

The Cullman quotation: I believe Cullman was chairman of the board of trustees, and the Cullman family has been one of the school's major supporters. Since Cullman is an alumnus and a prominent supporter, his comments on the school are worth noting.

Julian Houston is a judge in Massachusetts. As a successful legal professional, an alumnus, and a person of color, who has written a book that is clearly based on his experience at the school, it is appropriate to quote him on his time at the school.

Archibald MacLeish is among the school's most prominent alumni. Because of his stature, his comments on the school are notable.

Lemisch is both an alumnus and an emeritus history professor, who has written an article on the history of Hotchkiss. Because he is an alum and a historian, and because the subject of this article is the history of the school, a quotation from it is notable.

The above reasons support the relevance of these quotations to this article.

If there are other quotes by prominent alums who enjoyed their time at Hotchkiss, of course those would be worth citing here as well.