MacCulloch judges the Wolfson History Prize. Roughly 180 books a year cross his desk. He can sort them quickly. The first cut takes out books that are "too technical, written for other academics."1 The remaining books are then evaluated against the prize's actual criterion, which MacCulloch states plainly: this is fine history. It is beautifully written. It is therefore inspiring and exciting. And it must be available for a popular audience.1
When Perell asks what "beautifully written" actually means — what the mechanics are, what to look for — MacCulloch's answer is unguarded. "I'm not sure, frankly." He starts ruling things out before he can rule things in. Purple prose is "definitely a downer." Any prose that is purple is "not appropriate." Then he works toward a positive description: "Something which shows that the historian writer can sympathize with another human being and illuminate them for a third person. That's very difficult to define. I like it if it makes me smile. I suspect it if it makes me laugh. But a sentence which can make me smile two or three times and still subsequently make me think that's clever and illuminating — that's good prose."1
Read the test carefully. It's not the laugh — which MacCulloch is suspicious of. It's the smile, repeated, and still holding up to subsequent reflection as both clever and illuminating. The laugh is a one-time payoff; the smile that holds up under reflection is sustained virtue. The historian who can produce sentences that pass this test is doing something specific: she is being witty and substantive, in the same sentence, in a way that survives re-reading.
MacCulloch defines the criterion partly by what it isn't.
Purple prose is the over-stuffed version. Flowery vocabulary, ornate structures, prose that calls attention to itself as prose. "Any prose which is purple is not appropriate." It's not appropriate because the ornament gets in the way of the work the prose is supposed to do — illuminate the subject for the reader. Purple prose is the historian showing off.
Leaden prose is the opposite failure mode. "Leaden prose that which is cliche written which is unimaginative."1 It's the prose of competent but uninspired academic work — sentences that convey information without lifting it, paragraphs that move forward without producing recognition, chapters that say true things without making the reader want to read the next chapter. MacCulloch is careful not to despise leaden prose; he says it has its place ("the sort of book which can feed in to the wider conversation"). But it's not what wins the Wolfson.
The space between purple and leaden is where the criterion lives. The historian who can write inside that space — neither showing off nor settling — is producing the prose MacCulloch is looking for.
The criterion would be elitist if MacCulloch stopped there. He doesn't. Immediately after explaining what the Wolfson rewards, he makes a careful concession that's worth quoting at length:
"If they're writing about the provision of water supply in 19th century Wigan that is fine. That's that's not the sort of book which is likely to win win the Wolfson prize. But I don't despise it. It's the sort of book which can feed in to the wider conversation about history and its period and perhaps other periods too. So horses for courses. Great writing in history is is not what all historians ought to do."1
The phrase "horses for courses" carries the whole position. Different kinds of history serve different functions. The Wolfson-grade beautifully-written history exists. The technical-monograph water-supply history also exists. Both are legitimate. The technical monograph isn't aiming at the Wolfson criterion; it's aiming at the discipline's internal knowledge accumulation, where what matters is precision and contribution rather than narrative pull. The disciplined historian recognizes that her work serves one function or the other, and she calibrates her prose accordingly. The Wolfson criterion is not a universal standard; it's a task-specific standard for one kind of history.
This matters because it protects the criterion from becoming a stick to beat lesser stylists with. A historian writing a technical monograph on water supply in Wigan is not failing the Wolfson criterion; she is doing different work. The criterion only applies to history that's aiming at a popular audience. Within that target, the criterion is exacting. Outside that target, other criteria apply.
This runs deeper than first appears. The discipline of history needs both kinds of work — the popular-grade Wolfson winners and the technical-monograph contributors. The popular-grade work makes the discipline visible to the wider culture and recovers readers for the longer project. The technical work accumulates the granular knowledge that the popular-grade work eventually draws on. Each is parasitic on the other. The historian who writes only popular history is dependent on the technical scholars; the technical scholar who never reaches a popular audience is dependent on the popular-grade synthesizers to make the discipline matter outside the academy. A healthy field has both.
Later in the interview, MacCulloch returns to the entertainment criterion and qualifies it further. "I am very easily bored. And if a book is boring me, it's not entertaining me, that's a black mark against it. Another thing, criterion for the Wolfson Prize judging. It's got to be entertaining."1
Then immediately: "It's got to be entertaining without making a fetish of it."1
The qualification matters. The historian is not aiming at maximum entertainment. She is aiming at sufficient entertainment to keep the reader reading, in service of conveying the historical material. The fetish-version of entertainment is when the prose starts prioritizing the laugh over the illumination — when the historian is performing for the reader rather than communicating with her. That's where the smile-vs-laugh distinction comes from. The smile is in service of the material; the laugh is the writer's reach for applause.
MacCulloch's positive specification: "I like crafting a sentence which is funny. But it must be funny in a constructive way. Irony is the good side of it. It must tell you something about the subject. But occasionally it can just be bizarre because human life is bizarre."1
Three tools, in increasing order of risk:
Irony — the safest. Irony is humor that depends on contrast or reversal, and it almost always reveals something about the subject when used well. MacCulloch uses irony often; it's compatible with the disciplined-history criterion because the irony itself is information.
Funny constructive sentences — riskier but legitimate. The witty sentence that lands the smile and illuminates. This requires the prose to do double duty, which is hard, and the historian who can produce these reliably is unusual.
Bizarre — riskiest. Sometimes the historian can simply present material that is genuinely strange, and the strangeness is itself entertaining without any rhetorical work. This works because "human life is bizarre" — there is real comedy embedded in the actual historical record, and the historian's job is sometimes to let it through rather than smooth it over. MacCulloch admits to inserting bizarre material into his very large volume on sex and Christianity, "which of course veers into things which are probably not true, but are extremely funny."1 The double-bind is that the bizarre material has to be handled with sufficient discipline to remain history rather than become entertainment-for-its-own-sake.
How does the historian actually run this in practice? Several moves:
Audit the prose for purple stretches. Sentences that show off — ornate vocabulary, baroque structures, virtuosic transitions — get marked and trimmed. The test is whether the ornament earns its keep by doing illumination work. If it doesn't, it's purple.
Audit the prose for leaden stretches. Paragraphs that convey information without lift get marked and rewritten. The test is whether a curious non-specialist reader would want to keep reading after this paragraph. If not, the paragraph needs a sharpening pass — usually adding a specific concrete detail, a small dramatic move, or a calibrated piece of wit.
Test sentences against the smile-three-times standard. Not every sentence; some sentences need to be plain workhorses. But periodically — say, every page or two — there should be a sentence that's sharp enough to make a reader smile and still hold up to re-reading as both clever and illuminating. These sentences are what makes the prose distinguishable from competent academic work.
Watch for the laugh-temptation. When a sentence is reaching for a laugh — a punchline, a joke, a clever quip that's primarily about being clever — back off. The laugh is the fetish version. The smile-with-illumination is the discipline.
Calibrate to the target audience. A book aimed at general trade publication runs the entertainment criterion more aggressively than a book aimed at scholarly specialists. Both can be excellent; they're aimed at different readers. The "horses for courses" recognition prevents either book from being judged by the other's criterion.
The Wolfson Prize as institutional evidence is strong: the prize has been running for decades and has identified historians (Mary Beard, Tom Holland, Hilary Mantel — even as novelist — and many others) whose work meets the criterion. The criterion can be operated, and the results are recognizable.
Tension: the criterion is partly subjective. MacCulloch admits "I'm not sure, frankly" about what beautifully written means. The smile-three-times test is concrete but depends on the judge's taste. Different judges with different sensibilities produce different rankings of the same books. The criterion is institutional rather than purely formal — it requires a community of qualified judges who share enough sensibility to converge on rankings, even though they can't fully articulate the basis of those rankings.
A second tension: the criterion privileges narrative-friendly history over forms of history that don't naturally lend themselves to narrative. Quantitative history, demographic history, structural history, certain kinds of economic and intellectual history — these can be excellent without being entertainingly written, because their subjects don't yield narrative easily. The Wolfson criterion may systematically underrate them. MacCulloch's "horses for courses" partially addresses this, but doesn't fully resolve the question of how the discipline values different forms of work.
A third tension: the criterion can be gamed. A historian who learns the smile-three-times rhythm can produce prose that hits the marker without doing the substantive work. The market produces such books. MacCulloch's discipline is to refuse them by attention to whether the witty sentence is also illuminating — but the gaming is real and the judge's attention to it has to be sustained.
Open questions:
Read Pink and the contract is foregrounded. You hand the reader the book and ask for nine hours and twenty-five dollars. In exchange, you owe them entertainment, diversion, utility, a wider sense of the world, a capability-shift they didn't have before. Don't deliver and you've violated the contract. MacCulloch is running the same contract but with one more clause added on top: the historian also owes trustworthiness. The reader of trade nonfiction wants to be amused and informed. The reader of trade history wants those things plus the assurance that what's claimed about the past is actually defensible. Pink's contract is hard. MacCulloch's is harder. The Wolfson criterion is the contract specified for the harder version.
Walk through Deen's twenty-seven-pattern framework next and you can feel the operational version of what MacCulloch operates by taste. Where MacCulloch reads a sentence and says "this makes me smile twice and survives reflection, good prose" — and can't fully tell you why — Deen would point to the hook pattern and the finale pattern and the sound pattern and the tone pattern and decompose the working sentence into its components. The two writers aren't disagreeing; they're meeting at different points on the implicit-to-explicit axis. MacCulloch operates by accumulated sensibility; Deen makes the sensibility teachable. A young writer trying to develop the smile-three-times capacity probably gets there faster via Deen's decomposition than via MacCulloch's example. Once she has it, she'll run Deen's apparatus mostly unconsciously, the way MacCulloch already does.
Sit with Orlean on "story-as-yarn-elevation" and the same elevation function appears at a different scale. Orlean takes a New Yorker-grade subject — a man stealing orchids in Florida — and elevates the material from factual report to literary yarn. MacCulloch takes the documentary archive and elevates it to story-worthy prose without distorting what the record actually says. Both writers are running prose elevation. What they're protecting during the elevation differs: Orlean is protecting the subject's specificity, MacCulloch is protecting epistemic discipline. The constraint shapes what the elevation looks like. Orlean's prose can be more lyrical because she doesn't owe the same kind of evidential transparency; MacCulloch's prose lifts the material a little less because the hedges and qualifications stay in.
Then read Karlsson on "lowered promises" and the apparent tension arrives. Karlsson wants you to under-promise the reader so you have freedom to over-deliver. MacCulloch wants you to write to a high institutional standard — Wolfson grade, popular audience, beautifully written. Try to run both and you feel the friction. The resolution is that they operate at different points in the book. Karlsson's lowered promise is what you say upfront — "this is a small essay about an obscure observation" — while MacCulloch's high standard is what you deliver in the prose itself. You can write a book whose introduction says it's just a small history of Tudor church politics and whose execution holds up against the Wolfson criterion. Lowered promise + high execution = the reader experiences over-delivery and the writer kept her freedom. The combination beats either principle alone.
The criterion connects to writing-craft literature broadly, to the literature on comedy and humor, and to the institutional-incentive literature on what fields reward.
Creative Practice: Reader Promise Principle (Pink) — the underlying contract between writer and reader. The Wolfson criterion specifies what the historian's side of the contract looks like in this domain. The handshake produces the recognition that historiographic discipline is partly a discipline of honoring the contract more than other writers have to, because the historian's claims have stakes (truth-claims about the past) that recreational writing doesn't.
Creative Practice: Hook as Opening Compression (Deen) — the operational technique for sentence-level entertainment. MacCulloch's smile-three-times standard is the disciplined version of hook-quality measurement. The handshake produces a craft connection: the hook-as-compression literature gives the historian operational tools for hitting the Wolfson criterion at the sentence level, even when she doesn't have MacCulloch's accumulated taste.
Behavioral Mechanics: Entrainment and Rapport (or analogous Hughes/Lieberman page) — entertainment is partly an entrainment device. The historian who can produce smile-three-times sentences is entraining the reader's attention to the historian's voice, which then allows the substantive material to land. The handshake produces an operational frame: entertainment is not decoration; it is a trust-building mechanism that earns the reader's continued attention. Without it, the substantive material doesn't reach the reader who isn't already committed to staying with the book.
Eastern Spirituality: Sadhana Practice Hub (or analogous page on rasa theory) — the Indic aesthetic tradition (rasa theory) developed precise vocabulary for what kinds of emotional response a text should evoke. The relevant Western category — "delight" — covers some of the same ground as MacCulloch's smile-three-times standard. The handshake produces a comparative frame: the Wolfson criterion is a folk version of a much more elaborate Indic theory of how texts work on readers, and historiographic craft could be enriched by engagement with the older theory.
Psychology: Evolutionary Psychology Hub — the cognitive-psychology evidence on attention as scarce resource makes MacCulloch's entertainment criterion a structural rather than aesthetic requirement. Readers have a finite quota of sustained attention. A book that doesn't reward the attention with the smile-three-times kind of sentence-level texture will lose them — not because they're shallow but because attention is metabolically expensive and readers are constantly making implicit tradeoffs about where to spend it. The Wolfson criterion isn't snobbery; it's evolutionary realism. The handshake produces a sharpened claim: the smile-three-times standard is what attention-economic theory predicts as the minimum threshold for a popular-audience book to actually reach its audience. Below it, the book may be technically excellent but functionally inaccessible — sitting on shelves, partially read, recommended without being completed.
Behavioral Mechanics: Entrainment and Rapport (Hughes / Lieberman, or analogous page) — entertaining writing performs entrainment on the reader at the prose level. Hughes and Lieberman describe entrainment in face-to-face interaction (mirroring, pacing, rhythm-matching); the historian who can produce smile-three-times sentences is doing the same work in writing. The handshake produces a practical insight: the writer who has studied conversational entrainment can deploy the same mechanisms at sentence rhythm and paragraph cadence, and the reader who is entrained will absorb the substantive content the writer is trying to deliver. Entrainment is not manipulation when the destination is honest understanding; it's the engine that gets the reader to the destination at all.
The Sharpest Implication
The criterion applies to almost everything you write, not just to history. The smile-three-times standard is a craft test for non-fiction prose generally. Almost no prose you encounter passes the test. Most academic writing is leaden. Most popular writing is purple. The intersection — substantive, witty, surviving re-reading — is rare. If MacCulloch is right, the world is full of writing that doesn't justify the time spent reading it, and the disciplined reader spends most of her reading time on the small fraction of work that does. The third-wire reading is that this fraction is much smaller than the published market suggests, and that recognizing it requires the disciplined development of the same taste MacCulloch uses for Wolfson judging. Most people don't develop that taste. They read whatever is in front of them, processing it as it comes. The reader who has developed the smile-three-times standard reads less, more slowly, and with more retention — because the work she chooses is actually worth the time.
Generative Questions