Updated on 1 December: I’d like you to take a moment to picture Hugh Grant in your mind’s eye. Got it? Good. Now, who do you see?

It might be Charles, the hopeless romantic of Four Weddings And A Funeral, or maybe it’s the carol singing prime minister of Love Actually. It might be – and, let’s face it, it almost definitely is – the deliciously bad Daniel Cleaver. Or maybe it’s the murderous Jeremy Thorpe of A Very English Scandal.

Whichever Hugh you land on, you’re guaranteed to wind up with a completely different version to anyone else. 

And that’s because the actor – now 60, and the villainous adulterer of Sky Atlantic’s The Undoing – point-blank refuses to be typecast.

When people got comfortable with the idea of him being the floppy-haired love interest of any romcom, he switched things up and stepped into the shoes of Bridget Jones’ love rat ex-boyfriend. Then, when we found ourselves leaning into the idea of him being our go-to ‘naughty but nice’ guy, he upped the ante once again with a manipulative politician role.

And now? Well, in The Undoing he’s a seemingly perfect paediatric oncologist who also just so happens to be a liar, a cheat, and (possibly) a murderer. Because obviously. And, in Charlie Brooker’s upcoming Netflix mockumentary about the events of 2020, he’s playing a “repellent” historian, too.

With that in mind, then, we’re taking a look back at Hugh Grant’s best film and TV roles to date, and using them to chart his cinematic evolution from romantic hero to pure villain.

Grab yourself a bucket of popcorn and come join us, why don’t you?

Four Weddings And A Funeral

As reported on 9 September: There were roles before this one, sure, but this is 100% the movie that put Hugh Grant on the romcom map. As the slightly bumbling and always tardy Charles, he attends ever so many weddings, is late for almost all of them, and develops a fear of marital commitment in the process, too. With all this playing out in the background, though, he falls head-over-heels for a beautiful American stranger – and gives us one of his sweetest, most sincerely smitten performances to date.

Sense And Sensibility

Edward Ferrars might be one of Jane Austen’s stuffier characters, but Emma Thompson’s dazzling screenplay transformed him into a modern, likeable love interest. He’s great with kids, for starters, and he’s not threatened by female empowerment (hell, he even teaches Margaret to fence). 

He’s awkward, and bashful, and loyal. And his heightened emotional sensitivity, combined with the traditionally masculine bedrock of clear-eyed rationality, makes every viewer’s heart jump when he pops by to declare his love to Elinor.

Notting Hill

Guilty confession: I fell hook, line and sinker for Hugh Grant’s William Thacker. Sure, he owns a house and a bookshop in Notting Hill. Sure, his idea of a good night out is an expensive dinner with his (similarly wealthy friends). And, sure, his swear word of choice is “whoops-a-daisy”. All that being said, though, his affable awkwardness made him feel incredibly relatable – as did his numerous attempts to cut ties with a lover he knew to be bad for him.

And, let’s face it, his attempt to masquerade as a journalist for Horse & Hound basically inspired my entire career. So sue me.

Mickey Blue Eyes

As Michael, Hugh Grant is still very much the love interest of this movie but he’s not exactly ‘good’. He lies to his girlfriend. He (unwittingly) becomes involved in a money-laundering scam. He lies some more. And he winds up the mafia, big time.

It’s a tiny dipping of the toe into the realms of movie villainry, but it’s a dip nonetheless.

Bridget Jones’ Diary

Aha, now we’re getting somewhere. As Daniel Cleaver, Hugh Grant is (to quote Bridget herself) an alcoholic, workaholic, commitment phobic, peeping tom, megalomaniac, emotional fuckwit, and pervert. He sends inappropriate emails to his subordinates, he sleeps with Mark Darcy’s cruel ex-wife, he cheats on our beloved Bridge. And yet…

Well, he’s still funny. And charming. And unabashedly himself. Yes, Daniel Cleaver is a bad guy – but he’s our kind of bad guy, y’know?

About A Boy

As Will Freeman, Hugh Grant very much embraces all the shades of grey that come with playing a hopelessly flawed character. He attends a single parent support group and pretends he has a two-year-old son, solely with the aim of picking up women. He covers up the murder of a hapless duck. He allows himself to be blackmailed into becoming a sort of surrogate big brother to young teen Marcus…

And yet, again, Will isn’t all bad. He comes clean about his shady past, after all, and he knowingly humiliates himself in order to protect Marcus from high school bullies. And he forms a sweet extended family with Marcus, Marcus’ mum, his girlfriend Rachel, and Rachel’s son, which hammers home the film’s message: “No man is an island.”

Two Weeks Notice

New York City real estate developer George Wade goes through lawyers the way other millionaire playboys go through girlfriends – and he treats Sandra Bullock’s Lucy more like his nanny than his equal. And that’s not all: he’s reckless. He’s greedy. He’s cynical. He engages in seriously sexist hiring practices, plays strip chess with colleagues, and doesn’t give one tiny rat’s arse about destroying the Coney Island community centre.

That is, of course, until he falls hard for Lucy and realises how much it would mean to her if he didn’t knock it down. Which sort of taints his redemption arc because… well, because he would 100% have knocked it down and carried on being an utter sleazebag if he hadn’t won the heart of a good woman.

Love Actually

We’re back to romantic hero, albeit briefly, as Hugh Grant’s portrayal of Love Actually’s prime minister is pretty… well, it’s pretty heartwarming. Save for the fact, of course, that he asks that Natalie be removed from his staff after finding her in a compromising position with the US president.

Why? Because he fancies her, obviously, and if he can’t have her, then no other man can. Hmm.

Paddington 2

In his first proper ‘bad guy’ role, Hugh Grant stars as struggling actor turned thief Phoenix Buchanan – and he’s bloody amazing at it, too. He’s funny, he’s twisted, and he gives us the sort of moustache-twirling villain that we can’t help but fall in love with.

Trust us when we say that every single scene is pure gold. There’s a reason, after all, Paddington 2 boasts a 100% ‘fresh’ rating on Rotten Tomatoes.

A Very English Scandal

Hugh Grant was applauded by critics for his portrayal of disgraced former Liberal leader Jeremy Thorpe. As in, yes, the same Jeremy Thorpe who, in 1979, was accused of conspiring to murder his secret lover Norman Scott.

It makes for dark viewing. Really, really dark. But Grant convincingly suggests a man who would have been capable of almost anything in pursuit of his sexual desires and political ambitions – without stripping away any of his character’s humanity in the process.

Watch it, if you haven’t already. Just know in advance that Grant’s own dad found the much-discussed ‘Vaseline scene’ too much to handle.

The Undoing

Fair warning: spoilers ahead.

Grant’s role in Sky Atlantic’s The Undoing seems, at first, ambiguous. On the outside, he’s a devoted husband and doctor. But, when a horrific murder occurs and Jonathan disappears, his wife is left wondering if she ever knew her husband at all. He’s an adulterer, yes, and a narcissist. He seems, too, to be something of a compulsive liar. And his mother insists he lacks empathy or remorse. 

But a murderer? Really? You’ll have to watch for yourself to find out.

Find out more about The Undoing here.

Images: Getty/Rex Features/Sky