ugh Grant made his name in the 90s as a squeaky-clean charmer, but anyone who has been keeping tabs on his career will not have been surprised to see him show up in the HBO miniseries The Undoing as an unhinged philanderer, attacking a man with his bare teeth in a prison-yard brawl. For a while now, the actor who used to warm our hearts has been doing his best to chill our blood. And he has been doing it pretty well: as a scheming politician in A Very English Scandal, as a scheming investigator in The Gentlemen and, best of all, as a scheming theatre impresario in Paddington 2. As mid-career renewals go, Grant’s has been one of the best and The Undoing, six hours of top-notch trash that wraps up tonight, has made the most of its newly depraved star. The reinvention of the romantic lead is hardly a new phenomenon – it is more than 75 years since Murder, My Sweet turned Dick Powell from a fresh-faced musical star to a whisky-addled noir antihero, but in recent years it has become an especially popular trope. Richard Gere, who, like Grant, found screen stardom by flirting faux-modestly with flattered young ladies, has lately gone to great pains to show off his ugly side. He forged a career from playing wealthy, winsome suitors, but his recent turns as a hedge-fund magnate (Arbitrage), a moneyed philanthropist (The Benefactor), a high-flying politician (The Dinner) and a Murdoch-esque media mogul (MotherFatherSon) have all helped to flip the twinkly-eyed archetype on its head. Gere’s message is clear: I’m not the white knight you all thought I was. Matthew McConaughey’s much-trumpeted career revival hinged on a similar embrace of his dark side, while the lure of evil was strong enough to transform Vince Vaughn from the affable man-child of The Break-Up into the limb-snapping lunatic of Brawl in Cell Block 99 and Dragged Across Concrete. Deliberately or not, this mass-reinvention of Hollywood lover boys offers a neat reflection of how public life has changed since their 90s and 00s heydays. A fair few of the romantic gambits attempted then (an arse-squeeze in a crowded lift, intimate messages via an online alter ego) are now more court-case than courtly. But if all that cheery prosperity and iffy gender politics was simply a reflection of its time, the years since – with the banking crash, the Harvey Weinstein revelations and spiralling social inequality – have delivered some harsh lessons in just what those films got wrong. Their male stars have leveraged this cultural upheaval – and their own screen personas – with good results, as well as a taste for topicality. Gere, whose high-flying, sex-buying business exec in Pretty Woman was once Hollywood’s idea of the dream bachelor, has spent the past decade demonstrating the moral bankruptcy of the super-rich. Grant used his role in A Very English Scandal to show how a facade of bumbling charm can be the perfect foil for cut-throat political careerism. In The Undoing, his grubby affair with a naive young murder victim-in-waiting makes you worry for the fate of Martine McCutcheon’s character in Love Actually. The strategy has been clear: out with the charm, in with the smarm. But this career-shift is also a reflection of the roles available to A-list movie stars as they inch into middle-age. Half of them, anyway: it is worth noting that the former sweethearts of Grant, Gere et al have had to take different paths to remain at the top, or else risk disappearing. Julia Roberts and Sandra Bullock have navigated the post-romcom world by remodelling themselves as Hollywood’s elder stateswomen, leveraging their status into empowerment fables (Erin Brockovich, Eat Pray Love), worthy Oscar-bait (Extremely Loud & Incredibly Close, Ben Is Back, The Blind Side) and the odd once-in-a-career masterpiece (Gravity). Some of these movies have been good, others less so. But all have insisted their stars stay resolutely likable. The one film – or the one non-animated film – that did allow Bullock to enter the moral murk, Our Brand Is Crisis, was a box-office disaster. She has been one of the lucky ones: Meg Ryan, the definitive star of the romcom era, male or female, has not appeared on screen since 2016. Renée Zellweger has appeared in UK cinemas twice in the past 10 years – although she played a hammy baddie in Netflix’s gender-flipped version of Indecent Proposal, What/If – and Kate Hudson has all but disappeared. Those career trajectories reveal plenty about how the golden-era romcoms, with their airy happily-ever-after lessons, were probably not as wholesome as they seemed. But for a more visceral version of the same message, tune into The Undoing to see the foppish bachelor of yesteryear reborn as a grizzled and bloated washout, his tailored tux traded in for an orange jumpsuit. It is a nice metaphor for the way the world has turned rotten – and proof that glorious renewal is always within reach. The finale of The Undoing airs on Sky Atlantic at 9pm on 30 Nov