The Definitive Ranking of Hugh Grant's Romantic Leading Roles

An appreciation of three decades' worth of blue eyes, grins and inimitable bumbling charm from the British actor, who plays sweetheart and cad with equal aplomb.

By Natalie Finn Sep 09, 2020 7:00 AMTags
Hugh Grant, 60th Birthday, MoviesShutterstock; iStock; Melissa Herwitt/E! Illustration

Hugh Grant would be the first to tell you, don't believe the hype.

"I get very annoyed when people think that I am, sort of, nice, or diffident, or a polite gentleman or Englishman," he said on Watch What Happens Live in 2015. "All of those phrases make me gnash my teeth. I'm a quite nasty piece of work and I think people should know that."

If it makes him rest easier, we were never under the impression that he was just some "polite gentleman," even before his own personal baby boom that required a flow chart to keep track of how seemingly overnight he was a father of three with two women.

Rather, Grant (now a married father of five) has always just brought a certain something to his half of a love match onscreen, resulting in an IMDb page full of appealing suitors who invariably have their issues (a fear of commitment, a walled-off heart, he's prime minister), but nothing insurmountable—and no matter how much bumbling they do on their way to getting to the point, they always end up saying the right thing.

Best Hopeless Romantic Movies

The master of dunking on himself in service of the most satisfying outcome is turning 60 today. And while he's been leaning into more complicated roles in recent years ("Getting older and uglier has made the parts, you know, more varied," he quipped to Radio Times in 2018), even his most dramatic turns—including his Emmy-nominated performance as MP Jeremy Thorpe in A Very English Scandal—employ his signature cheek.

Watch: Hugh Grant on What Makes "A Very English Scandal" So English

It looks as if he'll be going darker still in the upcoming HBO miniseries The Undoing, but he left a blazing trail of some of the world's favorite romantic movies in his wake—some funnier than others (and some just better than others), but all benefiting from Grant's charm.

So, in celebration of his milestone birthday—and the fact that he isn't insisting on continuing to play the same sort of part that made him a huge star only paired with actresses half his age—here's our scientific, definitive, impossible to argue with ranking of his key films in which his romance with another character drives the plot:

14. Nine Months

This 1995 comedy was supposed to be Grant's big studio-movie follow-up to Four Weddings and a Funeral—and it was, only it hit theaters barely two weeks after the actor (who at the time had been dating Elizabeth Hurley for years) was arrested for soliciting a prostitute in Hollywood. He later pleaded no contest to lewd conduct with a prostitute.

"It did well, but it might have done better had I been better, and had I not been arrested the day before it came out. I screwed it up," Grant cracked in the 2019 BBC2 special Hugh Grant: A Life on Screen.

But Nine Months didn't make the bottom of this list because of the actor's off-screen peccadilloes. Rather, it's because Samuel Faulkner, a child psychologist who starts to unravel when his live-in girlfriend Rebecca (Julianne Moore) tells him she's pregnant—spoiler alert, he's just really afraid he's going to be a bad dad—is selfish and ridiculous until he redeems himself at the 11th hour and becomes perfect husband-and-father material.

Thanks to the supporting cast of Tom Arnold, Joan Cusack, Jeff Goldblum and Robin Williams, the movie is funny (and it was far from a flop, earning $138 million at the box office), but the so-called rom part of this rom-com is a bust.

"Brilliant actress, loathes me," Grant said of Moore (presumably facetiously, maybe?) when asked by Elle magazine to share some thoughts on his leading ladies (a trip down interview-memory lane he was reminded of on The Graham Norton Show).

13. Did You Hear About the Morgans?

Well, you may have heard about them, but then you just as quickly forgot about them after seeing this widely panned 2009 comedy starring Grant and Sarah Jessica Parker as Paul and Meryl Morgan, an estranged New York power couple (he's a cheater, so ew) who have to go into witness protection (in small-town Wyoming, hence the cowboy hats) after they see a hitman kill on of real estate agent Meryl's clients.

What do you know, rural life brings Paul and Meryl together (and their new good-hearted friends prove indispensable when the mob catches up with them). But while the chemistry that's supposed to be at the heart of the film fizzled, off-screen Grant and SJP seemed to get on famously.

"He lived up to and far exceeded my hopes and dreams," Parker told at the time. To which Grant said, "It's very nice to hear it from her. I'm very proud of liking her because I don't like anyone. I'm also very proud of respecting her because there are very few people I respect. In New Mexico [where they filmed] I would watch Sex and the City every night and call her and say, 'I love this episode!'"

12. Mickey Blue Eyes

Courting-and-figuring-it-out is where nice-guy Grant excels, but in this 1999 comedy he gets engaged to the girl, Gina (Jeanne Tripplehorn), early on, and genteel auctioneer Michael is left to get on the good side of her mobster father-in-law, Frank (James Caan)—a fish-out-of-water scenario involving organized crime and people faking their deaths and other hi-jinks in a movie that's tonally all over the place.

Worth stopping, when you flip by on cable, for the scene in which Grant, pretending to be a New Yorker in front of some of Frank's buddies, tries to order a steak cooked "ruuuah." 

11. The Rewrite

It's not bad at all, but did anyone see this 2015 film about an increasingly uninspired Hollywood screenwriter who finds his inspiration when he falls for a single mom taking classes at the college where he has a gig teaching screenwriting?

This marked Grant's fourth outing with director Marc Lawrence, who hit the jackpot with their first collaboration, Two Weeks Notice, but struggled over the course of Music and Lyrics and Did You Hear About the Morgans? with the wrong lead pairings. Grant and Marisa Tomei make this movie happen, and always-good J.K. Simmons and Allison Janney are also lurking in this cast.

Points detracted for writer-teacher Keith's stereotypical dalliance with another student, Karen, played by Bella Heathcote, before he meets Tomei's Holly.

10. Music and Lyrics

This 2007 movie—about a washed-up pop singer trying to reboot his career as a songwriter who gets a boost from the talented newcomer he falls in love with (like A Star Is Born, only happy and without the ravages of addiction)—is fine, but Drew Barrymore's movie husband is Adam Sandler, so this pairing was problematic for us.

9. Florence Foster Jenkins

Grant received his fourth Golden Globe nomination (and first since 2003) in 2017 for his turn as St. Clair Bayfield, actor and longtime companion of the title heiress—played by Meryl Streep—who didn't have a lick of singing talent but had plenty of money to finance her big break all the same.

It would seem as if Bayfield, who spends the first bit of the movie living with his mistress Kathleen (Rebecca Ferguson), is largely a cad, but he truly does care for Florence (the real-life pair were together from 1909 until her death in 1944), who's in decline due to the effects of syphilis she caught from her first husband. Bayfield does everything he can to fulfill her performance aspirations and protect her from hearing what the critics have to say—though he can only do so much in that respect.

Not exactly an ideal romance, but definitely a love story.

8. Maurice

Stupid turn-of-the-20th-century social constraints! In this James Ivory-directed period romance from 1987, Grant (in one of his first film roles) plays the aristocratic Clive Durham, whom James Wilby's title character first meets as a student at Cambridge. Their friendship-and-more endures, but alas, Clive, no matter how much he loves Maurice, decides he can't risk his social status by living publicly with another man and, under pressure from his mother, marries a clueless rich girl.

Maurice eventually finds love with Rupert Graves' Alec and Clive is left to ponder what might have been. (Interestingly, 1987 is the year in which the thematically similar Call Me By Your Name is set; Ivory won an Oscar for his screenplay adaptation of André Aciman's novel.)

"I hadn't realized that it was significant in terms of what it said about being gay or anything, not as we made it, not really," Grant reminisced to BFI in 2018, sitting alongside Wilby. "But then, in subsequent years, as it came out and afterwards, [I received] so many messages from gay men"—"thousands," Wilby interjected—"or men who had been in the closet and now come out, saying 'that film changed my life, it was really important to me.' I had no idea we were making a film that might speak to people like that."

7. Bridget Jones's Diary and Sequels

Usually the point of Hugh Grant is to get over whatever the heck is wrong with him and triumph romantically in the end, but in this case, the caddish, unreliable Daniel Cleaver—no matter how much he genuinely cares for Renée Zellweger's Bridget—is no match for her true beloved, Colin Firth's Mark Darcy. But, like, we can totally see what Bridget saw in her bad-boy boss, and you can tell Grant enjoyed going rogue. 

"I'm sick of playing Mr. Nice Guy and I think everyone else is sick of it too," Grant said in 2001 about his pivot to playing the guy who doesn't deserve the girl.

6. Love Actually

Less time is spent on British Prime Minister David-something's indecisiveness due to the ensemble nature of this Richard Curtis-directed rom-com classic, but it's there just the same (and he appears to spend way more time on it than he does attending to affairs of state). Hats off to Martine McCutcheon's brave Natalie, the staffer he fell in love with before transferring her to a different department so he could get some work done, for being the only one who can just come right out and write her feelings down in a Christmas card.

But at least he puts in the work in the end, going door-to-door to find her instead of utilizing the full power of the British government to find out which flat in that long row is hers.

5. Sense and Sensibility

Grant isn't onscreen all that much, but it's enough for his Edward Ferrars to fall in love with Emma Thompson's Elinor Dashwood, and she with him, though he's called away right when he's about to tell her and then she finds out he's engaged to someone else and no one can come right out and say anything because it's only 1810...

Oh, our hearts. But when exhaustively loyal Edward is disinherited and loses the "affections" of his fiancée Lucy Steele (Imogen Stubbs), he's at last free to propose to Elinor, and all is well. There's no big payoff (damn those 19th-century mores), but the look in his eyes when he kisses her hand on their wedding day says it all.

4. Two Weeks Notice

A better boss-falls-in-love-with-his-employee movie than Love Actually, Grant's hapless billionaire real estate developer George doesn't know that what his life is missing until Sandra Bullock's do-gooder lawyer Lucy puts it in order—and becomes indispensable, both to his business and his heart.

Make that takeout for two, Mr. Wong.

3. About a Boy

Wealthy slacker Will Freeman, an heir to his songwriter father's royalties, has a lot of mess to undo after pretending to be a single dad to ingratiate himself with Rachel Weisz's Suzie—a lie that leads to his unexpected bonding with Nicholas Hoult's Marcus, whose own single mom, Fiona (Toni Collette), is battling depression.

Starting a relationship off on a fraudulent foot is never a great sign, but Will is truly repentant and, in one of Grant's most heroic gestures onscreen, ends up saving Marcus from total embarrassment at the school talent show—a sign that this man-boy is growing up.

2. Four Weddings and a Funeral

The 1994 comedy directed by Mike Newell, with a screenplay by Richard Curtis, put Grant and his twinkling blue eyes on the map in America—and for good reason. Marriage-averse Charles is gobsmacked by fellow wedding guest Carrie (Andie MacDowell) right away, but is apparently so afraid of forever and making a mess of things that he doesn't call her after their (first) one-night stand, and three more weddings (one of them hers and another his) must ensue before he proposes that she spend the rest of her life not married to him.

Don't worry, he says it with a certain amount of charm. 

Grant won a Golden Globe for Best Actor in a Motion Picture, Musical or Comedy, and the movie was nominated for Best Picture and Original Screenplay Oscars.

1. Notting Hill

As far as Grant characters go, travel book shop owner Will Thacker—whose life changes forever when Anna Scott (Julia Roberts, ironically playing one of the most famous actresses in the world) walks into his store—slightly edges out his other winningly perplexed-looking suitors who find themselves head over heels in love but not quite sure what to do about it.

He's got a business, a nice flat with a bright blue door and an entertaining, supportive circle of friends. Aside from his hesitation over his valid concern that their lives are too different for it to ever work out, Will is pretty perfect.

"I think the big lesson is that romance is a big lie, perpetuated by cynical films made by Englishmen," Grant told WWHL host Andy Cohen in 2015 when asked what his takeaway was from his most popular films. "Don't fall for it. Because on the whole, it will make you miserable."

He did seem to recalibrate around that time, his turn in Florence Foster Jenkins in 2016 proving to be his most layered role in years (and critics took notice). Asked if he saw any more romantic comedies in his future, the actor told Radio Times in 2018, "That bird has flown."

As Grant has proven, however, he's not so hell-bent on doing drama that he won't participate in lighthearted fare such as "Red Nose Day Actually" and "One Red Nose and a Wedding," the TV shorts he did in 2017 and 2019 for a good cause, his reunions with the Love Actually and Four Weddings casts giving fans a nostalgic thrill.

And even if his befuddled-suitor days are behind him, he can't help it if, no matter what kind of character he's playing, there's always a twinkle in his eye. That's why you hire Hugh Grant.