Tyler Cowen interviews Henry Oliver, research fellow at Mercatus and author of Second Act about late bloomers. Oliver also writes a substack and co-authors another with Rebecca Lowe on liberalism.

The conversation centers on Shakespeare's Measure for Measure, examining why this problem play fell into non-popularity and what it reveals about justice, mercy, and Christian governance. Oliver argues it picks up where The Merchant of Venice leaves off, exploring whether mercy can actually exist in human government.

They discuss how the play's ending violates expectations - Isabella faces forced marriage while Angelo gets off relatively lightly. The conversation expands to cover Oliver's background in advertising, his views on late bloomers, and wide-ranging literary opinions from Gulliver's Travels to Atlas Shrugged.

Why Measure for Measure Fell from Favor

The play is 'very difficult to enjoy on the stage' with an unsatisfactory ending from an entertainment perspective - 'Shakespeare was experimenting with a comedy that had an unhappy ending'

The rapid delivery of Shakespearean acting makes the complex arguments hard to follow, and audiences want happier stories than this experimental form provides

On rereading, Oliver was surprised that 'the scenes between Isabella and Angelo are so enthralling and so passionate' - some of Shakespeare's best work rather than just a play of ideas

The Play as Christian Pragmatism

Measure for Measure continues themes from The Merchant of Venice: 'the quality of mercy is very strained, and it does not drop like the gentle rain' - mercy becomes 'a contrivance of human government'

The play demonstrates that 'no individual can be consistent with their own ideas' - Isabella repeatedly notes 'we cannot weigh our brother with ourself'

Shakespeare presents pragmatic resolution: 'either we sort of force everyone to get married, or they all end up worse off' - the alternative would be tragedy with multiple deaths

Isabella's Terrible Bargain

Cowen reads the play as feminist critique: Isabella 'gets a terrible outcome in all regards' - can't join the convent, must confront rulers, thinks her brother is executed, then faces forced marriage

The Duke takes Isabella 'without any of her consent' in what amounts to 'a form of rape or even worse, enslavement' with no property rights in the relationship

Oliver sees this as Kafka-esque reality where 'she in fact is good, and everyone else is the problem' - she's been 'broken' by the system's demands

Contrasts with The Rape of Lucrece

The Rape of Lucrece presents Shakespeare's first scenario: actual rape occurs, victim kills herself, autocracy falls because it's seen as evil

Measure for Measure offers different resolution through 'body tricks and substitutions and various deceits' - rape is avoided but autocracy stays in power

Shakespeare asks 'is that a better scenario?' - can artifice reconcile erotic and political tensions when the alternative is tragic death?

James I and Contemporary Politics

The play was performed at James I's court in 1604, addressing his interests in 'justice and law' and 'how to deal with religious tension, sexual behaviour south of the river'

References to the Duke not being 'inclined toward women' may allude to James's affair with the Duke of Buckingham and his reluctance to appear in public

Shakespeare presents pragmatic message James could accept: 'at the end of the day, the king is going to come in and impose the law, and that's just how it should be'

Jane Austen's Debt to Adam Smith

Austen took 'almost everything' from Smith - interested in 'how to be good in a commercial society' using his ideas for both moral content and narrative techniques

Her positioning of perspective and information delivery serves to show 'we have to create our own impartial spectator inside ourselves' - a very Smithian concept from The Theory of Moral Sentiments

Despite loving Shakespeare performances, Austen is 'one of the least Shakespearean of the English novelists' - distinguished as her own writer and thinker

Swift's Political Intelligence

Gulliver's Travels prepared Oliver for politics work: 'I was often startled by how much Swift understood about the day-to-day life of politics, the way people interact'

Swift has 'very different sort of intelligence to Shakespeare' - can deal with practical questions 'in both a fictional and a non-fictional manner'

Gulliver's Travels ranks as 'one of the very few great books ever written in English' with Swift managing 'not to express his own opinions' through incredible ambivalence

The Success of Second Act

Second Act succeeded because 'a lot of people want to be a late bloomer' and wanted 'a serious answer' rather than typical 'resilience and stamina' advice

Late bloomers often experience dramatic external events: 'Someone shoots themselves. They get caught in a hotel fire' - then decide 'I simply have to change everything'

Others 'become their own interruption' - looking in the mirror and saying 'really? You're going to die without doing it? You're not getting any younger'

Literary Ratings and Recommendations

Paradise Lost is 'easily one of the best poems in English, and it's not read enough' despite Johnson's criticism that 'no man ever wished it was longer'

The Faerie Queene is 'seriously underrated' and 'a top 10 work of all time' - even reading excerpts from the Oxford Book of English Verse reveals Spencer's 'great power'

Bleak House is 'the best novel in English' and 'really just an extraordinary piece of writing' - underrated among literary people who haven't read it

Atlas Shrugged is 'extraordinarily good' and 'maybe the best genre novel ever written' with 'first-rate B-movie dialogue' despite philosophical objections