Hugh Grant's best performances, ranked from least to most unhinged

Hugh Grant’s humble London-based bookseller Will in Notting Hill is as stable as they come—that’s the whole point of the character (it’s Rhys Ifans who gets to be truly unhinged here as his flatmate Spike). Will is a grounding presence in the looking-glass Hollywood life of American superstar Anna Scott (Julia Roberts). Despite a conscious effort to play against type in the years following his breakout role in Four Weddings And A Funeral, Grant reunited with screenwriter Richard Curtis after reading the script for Notting Hill, which was too good to turn down. Even now, two and a half decades later, it hasn’t lost any of its unapologetically romantic charm.

If Four Weddings And A Funeral solidified Hugh Grant’s status as a romantic lead, the Jane Austen adaptation Sense And Sensibility, released the following year, showed audiences that he could do it even better in period dress. His Edward Ferrars makes an enchanting first impression, but disappears for a good chunk of the film, reappearing only at the climax to haltingly reveal his true feelings to Emma Thompson’s Elinor Dashwood. That brief scene, and both Grant’s and Thompson’s performance in it, is the perfect capper to a bright and bountiful film full of memorable moments.

The unhinged length of this film’s title alone should indicate a non-zero level of whimsy without knowing anything else about it. And that’s not too far from the truth. With his star on the rise, Grant swerved away from larger scale productions and appeared in the quaint little indie The Englishman Who Went Up A Hill And Came Down A Mountain as a cartographer who travels to a Welsh village during World War I to assess whether the local geological feature qualifies as a hill or a mountain. Surrounded by colorful local characters, he does exactly what was expected of him at this point in his career. He’s a bit stiff, a bit flustered, and a bit charming, often all at the same time.

Unless you lived through it, it’s hard to explain the cultural impact that Four Weddings And A Funeral had on the mid-1990s. It was everywhere. And so was Hugh Grant, stumbling through a love confession to Andie MacDowell through the words of David Cassidy (when he was still with The Partridge Family). It was the first of what turned out to be several immensely successful collaborations between Grant and screenwriter Richard Curtis that catapulted him from a relatively unknown British actor to a worldwide star. As Charles, his boyish good looks are undercut by his social awkwardness, dry wit, and plenty of self-deprecation. The role would shape his career, for better or worse, for the following decade.

Before he became a recognizable star, Hugh Grant was making some real offbeat choices in film projects. Take for example, the late ’80s cult classic The Lair Of The White Worm, in which he plays a British aristocrat whose ancestral Derbyshire home happens to be situated next to a cavern inhabited by an ancient serpentine creature and the immortal priestess who serves it. Directed by Ken Russell and loosely based on a lesser-known Bram Stoker novel, it’s as bonkers as you might expect. As the plucky young hero, Grant doesn’t get to have as much campy fun as the baddies in the one, but based on some of his later performances, he was clearly taking notes.

Based on the book by Nick Hornby, About A Boy manages to be heartfelt without ever losing its edge. Grant’s layered performance as Will, an independently wealthy bachelor who forms an unexpected connection with a tragically uncool middle schooler (played by a babyfaced Nicholas Hoult), is a big part of why the film succeeds as well as it does. Will isn’t as romantically idealistic as some other characters Grant has played—he can be duplicitous and manipulative—but his heart’s ultimately in the right place. It feels like just the right balance of sweet and salty for Grant at this stage of his career.

Nine Months might be best remembered for a fluke of timing. It came out around the same time Grant was famously arrested for soliciting a sex worker near the Sunset Strip. The proximity of the two events meant that he had to do the press tour for the film while the scandal was unfolding in the tabloids in real-time, leading to an iconic interview with Jay Leno in which Grant defused the situation with his trademark self-effacing humor. That might have been his best performance of the year, though he’s not bad in the film as an increasingly nervous father-to-be. That said, we had to throw in a few extra points towards the unhinged end of the scale just for that extremely floppy hairdo.

In a film overstuffed with too many characters and intertwining plots, Grant’s storyline as the newly elected Prime Minister who falls for a junior staffer (played by Martine McCutcheon) has always stood out as a fan-favorite in Love Actually. Chalk it up to another successful team-up with screenwriter Richard Curtis. Grant now talks about how much he dreaded filming the famous scene when his character celebrates his political triumph over the American president (Billy Bob Thornton), but if he didn’t want the image of him dancing through 10 Downing Street to The Pointer Sisters forever burned into our brains, he shouldn’t have done such a good job at it. Afraid it’s too late now, sir.

Some of the best bits in Music And Lyrics were the scenes where the film played up the concept of Hugh Grant as a 1980s pop star, both in his heyday and as a washed-up has-been. It’s a fun metatextual angle that directly references Grant’s status as a romantic lead in a late-career rom-com. The big age gap between him and his co-star love interest Drew Barrymore could have been an insurmountable obstacle, but the two actually have a good amount of on-screen chemistry that works in the film’s favor. Perhaps the musical talents he showcased here led to more opportunities to make use of them in films like Paddington 2 and Wonka.

According to Hugh Grant, screenwriter Richard Curtis always found it amusing that he was so often cast as such nice, affable blokes when he’s quite the opposite in real life. That public-private contrast clearly factored into his role in Bridget Jones’s Diary as Daniel Cleaver, a modern equivalent of Pride And Prejudice’s dastardly Mr. Wickham. You can easily see why Bridget (Renée Zellweger) would fall for him, and when his true nature is revealed, it’s devastating. Grant’s performance makes Daniel’s turn from handsome heartthrob to loathsome slimeball seem all too real.

After Grant made the transition from nice guy to jerk in Bridget Jones’s Diary, he did the reverse as Sandra Bullock’s love interest and boss in Two Weeks Notice. He plays a rich, self-important real estate developer who hires Bullock as his Chief Counsel and becomes so reliant on her for his every need, she gets fed up and quits. It’s during the two weeks after she gives notice that the two of them realize they might actually like each other for real. The movie itself is a fairly standard by-the-numbers rom-com, but Grant and Bullock’s performances elevate it with an acidic chemistry that makes it fun to watch. Two rom-com giants at the top of their game.

Twenty years before he played drama king Phoenix Buchanan in Paddington 2, Hugh Grant sleazed it up as a predatory theatrical director in An Awfully Big Adventure, a heavy drama (don’t be fooled by the cheery tone of the trailer) based on the acclaimed novel by Beryl Bainbridge. Grant has played his share of villains over the years, but Meredith Potter might be the most despicable, because of how true to life his sociopathy feels. Reuniting with Four Weddings And A Funeral director Mike Newell, Grant seems desperate to shake off the shackles of typecasting with this film, set in dreary post-World War II Liverpool. Meredith is a monster who callously uses his position of power to prey on boys, girls, or anyone who shows the slightest interest. It’s a supporting role, but he nearly steals the show from co-star Alan Rickman (not an easy thing to do) and a young Georgina Cates.

In seeking to distance himself from the kinds of romantic roles he played earlier in his career, Grant has perhaps stumbled into another archetype that might suit him even better (and he would probably agree)—the overly theatrical narcissist. His character in Florence Foster Jenkins is another variation on that theme, and was acclaimed as one of the best performances of his career up to that point. Based on the true story of a wealthy socialite (Meryl Streep, who was nominated for an Oscar in the role) who believed she had talent as an opera singer because no one would dare tell her otherwise, Grant plays Florence’s husband and manager, St. Clair Bayfield. He’s a character with murky motivations, having given up his own acting career to support his untalented wife, and Grant lets you see all the interesting facets within him, even (and especially) the flaws.

Perhaps all the acclaim Grant received for his campy, over-the-top performance in Paddington 2 inspired him to take on another baddie in Dungeons & Dragons: Honor Among Thieves. From the moment we meet slippery rogue Forge Fitzwilliam, his arc from ally to adversary to the grandstanding Lord of Neverwinter is fairly predictable, but that doesn’t mean it isn’t tons of fun to watch Grant chew every bit of scenery within reach. Now that he’s fully in the DGAF phase of his career (just listen to any of his recent interviews), we’d encourage the directors of his future projects to let him off the leash more often. The results are frequently dazzling.

When filmmaker Paul King first sent the Paddington 2 script to Hugh Grant, the character of Phoenix Buchanan, a “washed-up narcissistic old actor” (in Grant’s words), was called Hugh. Grant could have chosen to take that personally and refused to have anything to do with the project, but instead, he embraced it. The performance he gives in the film is one of his best and one of his most unhinged. In a quest to hunt down a hidden treasure using clues from a pop-up book in Paddington’s possession, he employs a series of eccentric disguises to trick the poor, innocent bear. If Grant didn’t have a blast making the film, he did a fine job of making it look as though he did.