Henry Oliver on Measure for Measure, Late Bloomers, and the Smartest Writers in English

1. Read Shakespeare line by line. Oliver argues that with a play like Measure for Measure you cannot grasp the meaning by skimming; the wording is doing precise work, and characters constantly 'unstitch each other's words,' which is itself the play's pragmatism.
2. The play is a work of pragmatism. Oliver's core thesis: Measure for Measure shows that no individual can be perfectly consistent with their own principles, that abstract ideals can't be cleanly implemented by secular authority, and that forced, imperfect outcomes (everyone marries) are better than the alternative, in which people die.
3. Fiction changes beliefs the hard way. Reading fiction has no magical empathy-granting power; it works in a Smithian way only if you do the hard work of absorbing, testing, and arguing against it. Most of the time it just passes through you as a nice story.
4. Reading disagreements are mostly temperament. Differences in interpretation arise because fiction is intentionally ambivalent, because we lose context quickly, and because some readers seek more controversial readings — a disposition Oliver estimates is roughly 60% innate.
5. Good advertising fuses hard sell and image. Oliver credits David Ogilvy's 1950s synthesis of factual hard-sell and mood-based image advertising as what still works, and blames the 1960s 'creative revolution' for producing entertaining but ineffective ads that leave you unsure what was even being sold.
6. Late blooming has two engines. Late bloomers either respond to a dramatic external shock (a fire, a near-death event) or 'become their own interruption' — looking in the mirror and deciding to act before they die — and they tend to enjoy success more because they leave a bad life behind for something new.
7. Spenser and Bleak House are the great underrated works. Oliver names Spenser's Faerie Queene and Dickens's Bleak House (which he calls the best novel in English) as the two most underrated great works, both worth reading even in excerpt.
8. Reading can beat watching Shakespeare. Oliver largely agrees with Cowen that Shakespeare wrote to be read, not only performed; the best stage productions are minimal ones (like Jonathan Miller's) that simply ensure the actors understand the words, while interventionist directors usually distract.

Why Measure for Measure Fell Out of Favor

Oliver explains that the play long languished because it is hard to enjoy on stage. Its ending is unsatisfactory as entertainment, the dense arguments are difficult to follow at the rapid clip of Shakespearean delivery, and audiences generally want a happier story. Shakespeare was experimenting with a comedy that has an unhappy ending — a rare and deliberate combination.

The trouble, Oliver clarifies, is not that the ending is sad in the tragic sense but that it isn't the satisfying comic resolution audiences crave. Instead of lovers who want to marry getting their bells and dresses, the Duke essentially commands everyone to marry, prompting centuries of commentary asking whether any of these characters actually want to be married. Returning to the play, Oliver was most struck by how enthralling and passionate the scenes between Isabella and Angelo are — some of Shakespeare's best work — whereas he had 'ossified' into remembering it as a dry play of ideas.

What the Play Is Really About: Oliver's Pragmatism Reading

Asked to summarize the play's deeper meaning rather than its plot, Oliver argues it picks up where The Merchant of Venice leaves off, taking up the problem of mercy. In Merchant, Portia declares 'the quality of mercy is not strained... it droppeth as the gentle rain from heaven.' In Measure for Measure, Oliver says, mercy is very strained and does not drop gently — it is a contrivance of human government, and the question is whether we can actually have mercy at all.

He links the plays directly through Portia's lines at Belmont about how a candle's light shines in a naughty world, and Nerissa's reply that when the moon shone they did not see the candle, to which Portia answers that 'a substitute shines brightly as a king / Until a king be by.' That, Oliver says, is precisely the plot: Angelo shines like a king until the real Duke returns, at which point his authority drains away and we see him for what he is. The Duke echoes this at the play's opening when he says virtues go forth from us like lights, and that otherwise there'd be no point in having them.

Cowen offers a complementary reading: Portia was a great hypocrite in Merchant — preaching mercy to Shylock then breaking him because he's a Jew — and Angelo is the great hypocrite here, but in truth every character struggles to be consistent with their principles. Merchant says the Christian state can't be consistent with its own ideas; Measure for Measure says no individual can. Isabella insists again and again that 'we cannot weigh our brother with ourselves,' and the play's point, Oliver argues, is that you must weigh yourself in the balance — a very difficult thing that won't work well, leaving an arbitrary law imposed at the end. Spouting abstract principles only makes you a hypocrite; you simply have to make it work. Oliver therefore reads it as a great work of pragmatism, even invoking William James's definition of pragmatism as the unstitching of each other's words, which the characters do constantly.

Cowen's Three Readings and the Debate Over Isabella

Cowen advances three interpretations of increasing unorthodoxy, and Oliver pushes back on each, producing the episode's central debate.

A feminist (or anti-Christian) reading

Cowen argues the title is ironic — 'measure for measure' alludes to Christ's Sermon on the Mount, the idea that everyone gets back what they gave — yet the final deal is terrible for Isabella, whose expectations are violated in every way. She cannot join the convent, must confront her society's ruler, believes for a time that her brother has been executed, and is finally taken by the Duke without her consent, an outcome Cowen likens to a form of rape or even enslavement, with no property rights in the marriage. Angelo, by contrast, doesn't get what he wants either — forced to marry Mariana, whom he views as a strumpet — but his outcome is far less terrible than Isabella's. The unequal way Christian justice is doled out, with women getting the worst of it, makes the play, if not anti-Christian, deeply skeptical of Christianity.

Oliver reframes this as skepticism about a secular authority's ability to impose such rules in a world where men are mastered by vice. He notes that on the south bank of the Thames, where the playhouse stood, the dominant institutions were pubs, brothels, and bishops' residences — a London where these laws simply could not be enforced, which Shakespeare brings to the fore.

The Rape of Lucrece comparison

Cowen's second, less literal reading contrasts the play with Shakespeare's 1594 poem The Rape of Lucrece, where an actual rape by Tarquin occurs with no substitution, Lucrece kills herself, demands the deed be made public, and the autocracy falls because the act is seen as evil. That is one way to resolve the tension between the political and the erotic. In Measure for Measure, various imminent rapes are forestalled through the bed-trick, substitutions, and deceits; the autocracy survives, no one dies, and Shakespeare asks whether this artifice-based reconciliation is a better, more plausible scenario. Oliver agrees, reinforcing his pragmatism thesis: the alternative is not more happy marriages but tragedy, since had Isabella submitted to Angelo she'd likely have killed herself and others would have died too. He compares it to the contested endings of The Taming of the Shrew (is Kate broken or happily matched?) and All's Well That Ends Well (where, he argues, Bertram is so badly behaved that there's more justice and a possibility of happiness than in Measure for Measure).

The incest / fertility-crisis reading and Isabella's character

Cowen's third and least literal reading, which he admits may never have been Shakespeare's intent but which makes the play genius for him, notes the society's pervasive prostitution, bastardy, and cuckoldry, and the play's heavy 'brother and sister' imagery. In a world of rampant illegitimate couplings, half-siblings could be everywhere — making the society a kind of universal incest, and explaining why Isabella so absolutely refuses Angelo's bargain to save Claudio. On this reading she is the most aware character, sensing the incestuous nature of her society and wanting to retreat from it entirely; Cowen notes she even makes an explicit comparison to incest at one point.

Oliver declines to follow the incest argument, reading it instead as a fertility-crisis play. Lucio most loudly voices the worry that shutting down the brothels will harm the birth rate, and Oliver ties this to the play's pervasive coinage imagery — the stamping of a coin as a metaphor for procreation and demographics sustaining the economy. Isabella feels forced into the sex market, whether by marriage or blackmail, because the state needs a population; entering the nunnery is her way of preserving her principles and escaping that, and the Duke's final command that she marry reflects that there is no other way out of the fertility crisis.

On Isabella's character, Cowen points to her early line desiring 'a more strict restraint' and Lucio's 'Hail virgin, if you be,' wondering how virtuous she really is and whether she is protecting against her own tendencies. Oliver reads Act 1, Scene 4 oppositely: Isabella is asking whether the nuns are strict enough, criticizing a lax institution rather than revealing her own weakness, and Lucio's line mocks the nunnery, not her. Throughout, Oliver sees the individual standing out against the corrupt institution, with Isabella as a genuinely good figure trapped in a Kafkaesque reality where everyone else is the problem.

The 'I Did Yield to Him' Crux (Act 5, Scene 1)

The two spend extended time on Isabella's line at roughly line 120, 'and I did yield to him,' which Cowen finds genuinely confusing and which fuels his suspicion that she may have actually slept with Angelo (and may even be a subtle, highly effective seducer when she 'prays and kneels').

Oliver insists on a line-by-line reading. Isabella calls Angelo a 'pernicious caitiff deputy,' the Duke disputes her phrasing, and she replies that phrasing is everything — the first sign, for Oliver, of the play's pragmatism and its constant unstitching of words. She must phrase her accusation in a way the Duke will accept. When she recounts how she 'persuaded,' 'prayed,' and 'kneeled,' Oliver argues she is re-speaking Claudio's earlier description of her 'prone and speechless dialect,' and the genuine ambiguity is whether she persuades through speech or through an unwitting power to inflame Angelo — again echoing the coinage question of whether value lies in the metal or the stamped face.

Oliver reads 'and I did yield to him' as referring to the argument in Act 2, Scene 2, in which Angelo backed Isabella into conceding an inconsistency in her own position — she yielded the premise of his argument, not her body. The subsequent 'but the next morning he sends a warrant for my brother's head' refers to the arranged bed-trick with Mariana. Cowen counters that for Oliver's reading to hold, everyone (and the audience) would have to believe it was Mariana while Isabella and the Duke secretly knew it wasn't — which he finds unworkable. Oliver flatly disagrees, saying the lines read too cleanly into the known plot for Cowen's reading, while Cowen cheerfully concedes his is a non-literal reading.

James I, Catholicism, and Girard

On James I, Oliver notes the play was performed at his court (likely 1604) and was not otherwise hugely popular — there was no quarto — so it may have been written with the new king in mind. The theme of measuring oneself was current in Shakespeare's England (a morality play has Mercy advise 'measure yourself ever, beware of excess,' and the Puritans loved self-measurement), but self-judgment can't be the basis of public policy. A coronation sermon described a prince's duty to execute 'just judgment by which all must be measured,' and James was keenly interested in justice, law, religious tension, and sexual behavior. Oliver thinks Shakespeare took up these court-current themes; the Duke's eventual imposition of law is broadly flattering to James's own ideas of government. Cowen adds that no matter Shakespeare's intent, a smart playwright performing before the king couldn't escape the thought that connections would be drawn. Both treat the more specific speculation — that the Duke's apparent disinclination toward women alludes to James's affair with the Duke of Buckingham, or that the Duke's reluctance to appear in public mirrors James — as too speculative, though Oliver concedes the loose parallels exist. Oliver offers an alternative explanation for the Duke's non-interest in women: he and Isabella are mirrors (justice and mercy, temperance and passion, both pragmatically willing to deceive in a good cause), and their pairing works precisely because they are the least sexualized characters and thus, if Isabella must marry someone, the Duke is the least bad match.

On the recurring claim that the play reveals Shakespeare was a secret Catholic, both reject it firmly. Oliver says there simply isn't the evidence; the presence of friars, nuns, and pre-Reformation atmosphere is no basis, since Shakespeare is always writing about the tension between pre- and post-Reformation culture (as in Hamlet). He likens the Catholic-Shakespeare project to using numerical analysis of the Bible to predict Judgment Day. Cowen reads the play as mildly anti-Catholic — Vienna has friars and nuns yet avoids none of these problems, and pointing up the corruption of Catholic institutions is a thoroughly normal move in English literature.

Asked whether it is a Girardian play, Oliver hadn't reread Girard but argues it may be anti-Girardian. The substitutions only work because they are obviously fake — no one is genuinely a double — and the characters, especially Isabella, are driven by their own inner desires rather than mimetic ones; Isabella must be made to kneel at the end precisely because she is not mimetic. He contrasts this with cleanly Girardian plays like A Midsummer Night's Dream (lovers who switched allegiances before the play begins) and Troilus and Cressida (Troilus's desire reignites only when the Greeks want Cressida), and feels the Girardian framework has been stretched like bread dough far past its usefulness.

Favorite Lines, Reading vs. Performance, and Productions

Oliver's favorite passage is Isabella's 'but man, proud man, / Dressed in a little brief authority... plays such fantastic tricks before high heaven / As make the angels weep,' which he says periodically becomes relevant again. Cowen favors Angelo's 'we must not make a scarecrow of the law' and the Duke's 'the baby beats the nurse, and quite athwart / Goes all decorum,' praising how well they play in performance, plus the Duke-as-Friar's line about fearing 'the soft and tender fork / of a poor worm.' Both note Shakespeare's surreal, slightly absurd touches — comparable to Shylock's 'wilderness of monkeys' or the Taming of the Shrew maid who goes to the garden for parsley to stuff a rabbit and comes back married.

Cowen floats his contrarian view that the ideal way to experience a Shakespeare play is to read it silently to oneself, with any staging a dilution. Oliver agrees more than most would: Shakespeare wrote to be read as well as performed, knew anthologists copied down the good 'anthology speeches' to pirate them, and knew his quartos (a third to half of the plays) would be printed and sold. He served a divided audience — penny-payers in the pit and over-educated young men wanting Latin puns and legal debates to boast about — and that learned audience persists today. Oliver criticizes modern productions for over-interventionist directors with crazy metaphors, and praises the one excellent staging he saw, by amateur RADA students directed by opera director Jonathan Miller, whose method was simply to ensure the actors understood the words and then let them perform — much as Hamlet often succeeds on a bare dark stage with the words said properly.

On film, Oliver hasn't yet seen the 1980s BBC version (which features Helen Mirren as Isabella, a casting he can imagine working), and knows of no great film of Measure for Measure. His pick for the best Shakespeare films overall are the least 'Shakespearean' ones — Orson Welles's work, especially Chimes at Midnight — along with some 1980s BBC productions, a recent BBC Henry IV sequence with Tom Hiddleston, and filmed Globe productions, singling out Mark Rylance and Stephen Fry in Twelfth Night.

Jane Austen, Adam Smith, and the Novelists

Oliver says Jane Austen took 'almost everything' from Adam Smith: she is preoccupied with how to be good in a commercial society and draws on Smith not only for moral content but for narrative technique. From Shakespeare, Austen absorbed a love of the dramatic and theatrical (visible in the theatrical scenes of Mansfield Park) and much of his language, yet she is paradoxically one of the least Shakespearean of English novelists — to her great credit, being so distinctly her own writer and thinker.

Smith, in turn, drew heavily on the eighteenth-century novelists, loving Gulliver's Travels and Samuel Richardson. Oliver cites scholar Shannon Chamberlain's thesis on how details of those novels reappear in Smith's work, noting Smith reuses the novelists' very examples — including the trivial-but-useful objects (watches and the like) that Gulliver accumulates, which Smith discusses as trivial yet beneficial. Surprisingly for so liberal a mind, Smith endorses Richardson as a novelist to read for morals — perhaps his most surprising literary judgment. Oliver is less sure Smith took much directly from Shakespeare.

How Fiction Changes Beliefs

Oliver rejects the romantic idea that fiction has a magical power to grant empathy or make you nicer. Fiction changes beliefs by the same mechanism as anything else — and you can get the same from nonfiction, conversation, or film — only if you do the hard work of absorbing it, thinking about what it means, and testing your opinion against others' in the Smithian sense. Otherwise it passes straight through you as a nice story. He draws the parallel that moral philosophers do great work yet it rarely changes their personal morality; something similar limits fiction's effect.

On his own much-reread Gulliver's Travels, Oliver says reading it before working in politics (as a low-level 'bag-carrier') startled him with how much Swift understood about the day-to-day sociology of politics, and it was one of the factors that convinced him he shouldn't be working there.

Jonathan Swift, the Smartest English Writer

Oliver calls Swift the smartest English-language writer (Shakespeare possibly excepted), crediting Swift with a different kind of intelligence: he can handle a practical question — coinage, government, the conduct of a war — in both fictional and non-fictional registers, deploying either the directness and polemicism of his pamphlets or the radical ambivalence of Gulliver's Travels, a book in which he manages never to express his own opinions. Swift thus has a balance Shakespeare lacked, since Shakespeare did no non-fiction arguing, even though Shakespeare far exceeds Swift overall and Gulliver's Travels remains one of the very few great books in English.

Beyond Gulliver, Oliver recommends a small selection of Swift's poetry (to see how vicious, sharp, and wicked he could be, and how he enjoyed berating prostitutes), the lively and finely observed Journal to Stella, and the pamphlets — not only 'A Modest Proposal' but the Drapier's Letters, some of Swift's best work.

Why Readers Disagree About Books

Asked to explain why two not-very-opposed readers disagree, Oliver gives three reasons. First, fiction is intentionally ambivalent — Swift in Gulliver's Travels deliberately withholds his own opinions and gives readers room to get it 'wrong,' as most novelists do most of the time. Second, we lose the context of these books so quickly that we cannot help bringing ourselves to them. Third, some readers (Cowen among them, Oliver suggests, and Oliver agrees of himself) want to find more controversial readings than others. Oliver attributes much of this to temperament, which he and Cowen jointly estimate is roughly 60% innate. Temperament also shapes the creation of a book — Austen's is fundamentally different from Swift's — so readers are reacting to an author's temperament, not just their content.

Advertising and Its Discontents

Oliver spent nearly a decade in advertising and deliberately keeps it separate from his reading, calling it a 'pollution' of literature because advertising is not a great art and applying its principles would be a diminishment. Pressed by Cowen — who notes advertising offers genuine insight into what people value — Oliver concedes that if advertising means the calling of attention to something important, then many great writers (Swift above all, whose career could be reframed as world-class lobbying and PR) were superb advertisers of their own ideas. Oliver professes a 'Catholic' view of literature, admiring practical writers like Samuel Johnson who could write a sermon, a legal opinion, or an advert with equal facility.

On why advertising is mostly stupid and boring, Oliver argues it is not optimal. We still don't know how well advertising works, partly because privacy laws limit targeting; people overestimate how precisely they are targeted (the ubiquitous 'toaster ad' following everyone is crude, not real targeting). The field, he says, has been captured by bad ideas. He describes two schools: the hard sell (repeated product name, facts, studies — 'cures headaches three times quicker') and the image school (Theodore MacManus / Raymond Rubicam-style mood pieces like the Steinway 'instrument of the immortals,' the frosted-flakes tiger, the Marlboro Man). The 1960s 'creative revolution' — advertising's modernism — discarded the hard sell for relentless novelty, producing clever but often unnecessary work (the Volkswagen 'Think Small' Beetle ads, which Oliver notes would have sold themselves), and degenerating into the 1980s–90s mini-films (he cites a Levi's ad with a condom purchase and a minister's daughter eloping by train) that entertain but leave you unsure what was sold. The real, durable creative revolution, Oliver argues, was David Ogilvy's in the 1950s, joining hard sell with image — and Cowen notes that Oliver himself advertises effectively on his blog and podcast by blending the two.

Overrated vs. Underrated: A Literary Round

Cowen runs a rapid round and Oliver delivers verdicts with reasons.

Verdicts

Oliver rates Milton's Paradise Lost underrated and one of the best poems in English, allowing that Samuel Johnson's quip that 'no man ever wished it longer' is one of Johnson's rare clunkers. He calls Spenser's Faerie Queene seriously underrated and a top-ten work of all time that almost no one reads — even in the excerpts in the Oxford Book of English Verse you feel its power and magic. Galsworthy's Forsyte chronicles he finds overrated and crushingly dull, unable to finish them, though Cowen (who read all four) thought them good melodrama he never regretted. D.H. Lawrence's short stories he calls truly phenomenal — wild, strange, compelling — having gone back to them after thinking he disliked Lawrence. Dickens's Bleak House he calls the best novel in English and, with Spenser, one of the two most underrated great works. Tolkien (Lord of the Rings plus The Hobbit) is properly rated by fans but underrated by highbrows who dismiss it, sometimes without reading it, while clearly being among the great novels of the 20th century. Harry Potter he rates appropriately — genuinely good children's books that are exciting and fun (he bought them on release day as a young person), though he finds dressing up to visit King's Cross an act of overrating, and dismisses Harold Bloom's claim that they are cliché-ridden and deadening as rubbish.

American Fiction, British Overrating, and Science Fiction

Oliver admits he hasn't read enough American fiction and is trying to read more. He praises Henry Adams's Democracy (which Cowen agrees on) as genuinely good, short, and instructive for people in Washington. He hasn't gotten far with much 20th-century American fiction and is unsure whether that's his temperament or genuine overrating, but he is suspicious of certain 'big white male writers' being revived now. Cowen offers the structural point that a wealthy, populous country dominating academia (with The New York Times and other outlets) will end up with many overrated writers, and that it will take another generation to see what lasts. Pressed on whether Britain similarly overrates its writers given the TLS, the London Review, fine bookshops, and a literate population, Oliver discusses Barbara Pym, noting that Persephone Books' founder declines to republish her despite reviving many 20th-century women writers — suggesting more divided opinion than expected. He defends an omnivorous literary life embracing middlebrow, lowbrow, and trash alongside Shakespeare, and rates Pym properly, conceding people might profitably read a bit more Spenser instead.

On science fiction — a self-described gap — Oliver liked The Day of the Triffids (read at school) and Stanisław Lem's robot fairy tales (not Solaris, but good). He is watching Pluribus, having seen two episodes; he doesn't grasp how an RNA could merge everyone's minds (which he treats as a premise to accept, like the world of Star Wars, so long as the rest is consistent), but likes it and thinks the right dynamic is that some people want to join the so-called hive mind and some don't.

Mental Illness and Religion in Fiction

Asked for the best portrait of mental illness in English fiction, Oliver suggests Swift's A Tale of a Tub but says English fiction isn't very good at it; Cowen offers Septimus in Mrs. Dalloway, and Oliver names Gogol and the Russians as genuinely good at it.

On whether fiction can again deal seriously with religion, Oliver thinks it can and likely will before too long. Marilynne Robinson arguably does so now, but most strong examples (Evelyn Waugh, Willa Cather, Dostoevsky — whom Oliver doesn't like but credits) are earlier. He notes religious Substack writers point to current religious fiction without claiming greatness, and observes that the atheist preoccupation (the Martin Amis style) was itself a way of dealing with religion, bad for literature though it was. With many religious young people now, Oliver expects another Graham Greene or Muriel Spark within perhaps twenty years — and predicts it will be a young person and largely a convert, not a late bloomer.

Late Bloomers and Second Act

Oliver attributes the success of his book Second Act to a widespread desire to be a late bloomer — the book implicitly sold the hope of 'if only,' even as he explicitly argued against it — and to the fact that he gave a serious answer where other treatments offered only resilience-and-never-give-up clichés.

He identifies two engines of late blooming. In one, a dramatic external event (someone shoots themselves nearby, being caught in a hotel fire) prompts a person to turn around and decide everything must change. In the other, there is no sharp crisis; the person 'becomes their own interruption,' looking in the mirror and refusing to die without doing the thing. Cowen raises the Grandma Moses exhibit then on at the American Folk Art Museum in Washington, D.C.; Oliver, a fan of her paintings, classes her as the external-circumstances type: a house servant from age 12 or 14, then a farmer's wife with children and no domestic conveniences, who had done childhood arts and crafts but only resumed (encouraged by a sister-in-law to paint rather than stitch) once retirement gave her the time. Oliver believes late bloomers enjoy success more, because they leave the bad thing behind and move into something new — quoting David Ogilvy that men with multiple careers are to be envied, as the ultimate anti-boredom. On Ayn Rand, Oliver tentatively counts her a late bloomer if Atlas Shrugged is singular; having long avoided her because of off-putting objectivists he'd met, he read it on Hollis Robbins's recommendation and 'fell in love,' finding her handling of ideas far less clunky and more subtle than her reputation suggests (the party scenes, the train arguments), with villains 'remarkably true to current life,' though the three-hour speech wears on anyone.

Child-Rearing, Reading Advice, and What's Next

Drawing on time working in a school, Oliver's parenting advice is 'fun, firm, and fair' — applicable to boys and girls — and to be involved but not too involved, giving children their own space and letting them be children.

For readers approaching Measure for Measure, Oliver counsels them to decide for themselves how much apparatus they want: some readers thrive on every footnote of the Arden edition while others should just race to the end to find out what happens and then go back. From running online Shakespeare book clubs, he's found genuine variation — some readers want the painful blow-by-blow and some don't — so the reader should choose their own approach.

Asked what he'll do next, Oliver keeps it a secret, saying only that he has many things in his draft folder, some of which may get published. Cowen closes by recommending Second Act, Oliver's Substack, and his new joint Substack with Rebecca Lowe.