The world loves a hostile or challenging graduation speech, one that eschews the warmth and supportiveness and grand inspirational sweep of the usual thing. Take the recent, interestingly bitter graduation speech delivered by a Wellesley High School teacher, David McCullough, with his mild-mannered preppie demeanor, wire glasses, purple striped tie: “None of you is special. You are not special. None of you is exceptional.”

In one transcendent part of the speech, which on the whole flirts pleasingly with being entirely out of control, he says, “Across the country no fewer than 3.2 million seniors are graduating … that’s 37,000 valedictorians … 340,000 swaggering jocks … 2,185,967 pairs of Uggs.” Although he tries to end on a more uplifting note, and move the speech into more conventional territory of inspiration, and caring about other people, the true heat of the speech is in its critique of the emergent generation he believes is overly managed, overly protected, and exquisitely nurtured: “Yes, you’ve been pampered, cossetted, doted upon, helmeted, bubble-wrapped.” (Though really, read carefully, this is a critique of their parents.)

McCullough’s suggestion is that their confidence, their carefully bolstered self-esteem, might be unearned. He argues that they are operating under a false impression of their own centrality and vividness. (As he puts it, “hundreds gasp at delight with your every tweet.”) The speech could be read as very practical, useful advice for these students, an explicit, tough love exhortation to do something interesting, unusual, extraordinary, not just to think they are interesting, unusual, extraordinary. But it could also be read as a statement of finely wrought contempt.

Every time it happens that someone breaks out of the inspirational platitudes with a hostile or challenging commencement speech, people are ruffled and interested, and it seems like an anomaly or maybe a mistake. But these mini-nervous breakdowns in commencement speeches are a recognizable genre, borrowing heavily from the truth-telling ambience of a J.D. Salinger story or novel. The outward stance “I am not going to tell you the fake thing you think you are going to hear” is very common, though few achieve the authentic surprise, the true frisson of a graduation speech that shakes people up, and almost never does it get as good as “2,185,967 pairs of Uggs.”

The temptation to tell the gathered students—all dressed up under their graduation gowns, in the heat, the smell of fresh mown grass, the watercolor-blue sky, celebratory cakes in boxes on counters at home—something they are not expecting must be hard to resist for a certain kind of charismatic, boundary-breaking educator or writer or other distinguished person. There is rarely such a rich, glimmering possibility for upending platitudes and an audience so primed, so emotionally wrought, so unusually open to listening, so uncharacteristically reflective.

At my own graduation, the headmistress of my girls’ school gave an overtly hostile graduation speech enumerating in startling detail how difficult, theatrical, and irritatingly self-righteous the graduating class was. The rows of girls in white dresses felt extremely betrayed, along with their parents. She singled out the hypocrisy of a piece I had written for our underground newspaper, Samizdat, called “The Mystique of the Ivies” about how the school was pressuring students to go to Ivy League colleges, even though I myself, along with many of the other editors of this pretentiously subversive publication, was headed to an Ivy league college in the fall. She attacked us for our half-informed, rather-festive sit-in in the lobby against the school’s investment in South Africa. Sometime later she stepped down from her position and left the school.* It was widely believed that she had suffered some form of nervous collapse: The bracing originality of her act or performance piece was not appreciated, in part because she lacked the panache of McCullough, if not the simmeringly channeled rage.

David Foster Wallace’s famously excellent Kenyon commencement speech is not exactly hostile, but it is challenging (and if closely read, it is hostile to the complacency that McCullough is attacking, and to the future selves of the vast majority of the graduating seniors. Does that matter, though? Do any of them see clearly the settling, the mediocrity, the comfortableness they will embrace in coming years? Or do they all, down to every last “swaggering jock,” think of themselves as Holdens, as outsiders, as possessing of singular integrity and unique alienation? )

Michael Lewis’ recent charming, and mildly subversive, commencement speech at Princeton attributed his professional success to luck, specifically being seated next to the wife of someone who worked at Salomon Bros., at a dinner in his 20s. He then went on to discuss a psychological study about how people who were randomly assigned “leaders” in a group felt they were entitled to an extra cookie. In the most tactful way possible, he suggested to the gathered Princeton graduates that they had that extra cookie but should understand very clearly that they don’t deserve it.

When my mother was in high school, one of her suitors with literary aspirations wrote to J.D. Salinger asking him to write a letter addressing the graduates in the Andover yearbook. Somewhat surprisingly, Salinger wrote back to him, and the boy showed my mother the letter to impress her. Salinger had written something that could also apply to commencement speakers: “On the train to New York at Christmas time walk through the cars until you see a smallish boy struggling to get his suitcase up on the rack. He is sitting alone. He seems to have a cold and his nose is running. He is the one who should write to your graduates. Ask him.”

Correction, June 18, 2012: This article originally asserted that the headmistress stepped down soon after her commencement speech. She stepped down years later. (Return to the corrected sentence.)