10 Highest-Grossing Rom-Com Kings, Ranked

After fading from prominence for a few years, romantic comedies appear to be making a comeback, especially on streaming sites. Streaming makes it more difficult for actors to accumulate high box-office earnings, but films like Anyone But You are doing extremely well, showing that there is a market for romantic comedies. With Valentine’s Day coming up faster than anyone can spell it, some people are looking for their partner in crime, a yin to their yang, their other half—a king to their rom-com queen, one might say.

A few standout actors have made a career out of starring in romantic comedies, while others have only sporadically dabbled in the genre. Putting their good looks, humor, or simple charm to excellent use, actors have endeared themselves to their onscreen love matches, as well as to viewers watching the romance come alive. These actors dominated the rom-com genre and the box office for years, cementing their legacies as romantic icons of the silver screen. Now, the question is: will anyone in this new crop of swoon-worthy rom-com kings eventually overtake the current reigning champions of the box office?

10 Ben Stiller

Rom-Com Box-Office: $382M

Ben Stiller wrote for Saturday Night Live and worked as a featured performer on the sketch series for only four episodes before leaving the show. After his own The Ben Stiller Show was canceled, Stiller directed his first romantic comedy, Reality Bites, alongside ’90s “it-girl” Winona Ryder and grungy heartthrob Ethan Hawke. The film was a strong jumping-off point for Stiller in the genre, with his next few films, If Lucy Fell and Flirting with Disaster, not landing quite as well at the box office. But that would all change in 1998 with some “frank and beans” and questionable hair gel.

Also featuring Cameron Diaz in her breakout role, the Farrelly brothers‘ raunchy romantic comedy There’s Something About Mary more than solidified Ben Stiller as a leading man box office draw. Stiller’s unassuming visage made him accessible to all audiences, and his comedic timing and willingness to “go there” made him a star. He kept dominating the genre with rom-coms like Keeping the Faith with TV star Jenna Elfman and Edward Norton, Along Came Polly with Jennifer Aniston, and Duplex with Drew Barrymore. His highest-grossing films, however, skew toward awkward and often R-rated comedies.

9 Jack Nicholson

Rom-Com Box-Office $430M

Three-time Oscar winner Jack Nicholson isn’t the first person to come to mind when thinking of romantic comedies; indeed, he is mostly known for his intense dramatic roles. However, in As Good As It Gets alongside Helen Hunt, Nicholson showed he had a romantic side and won a Best Actor Oscar for his effort. Audiences loved seeing a different side to Nicholson, and he shared excellent chemistry with Hunt; even with their polar opposite characters and age difference, the romance was believable (if not entirely advised).

In 2002, Nicholson starred alongside Kathy Bates in Alexander Payne‘s dark comedy About Schmidt and earned another Oscar nomination for his work. The following year, Something’s Gotta Give became a huge hit, with audiences enjoying its exploration of love later in life and charming performances by Diane Keaton and Keanu Reeves. While Nicholson mostly kept his gruff demeanor, glints of tenderness toward both Amanda Peet and Keaton revealed his soft side. In 2010, the romantic comedy How Do You Know? marked Nicholson’s last film role to date.

8 Ashton Kutcher

Rom-Com Box-Office $432M

Who would have thought that playing the goofy stoner Kelso in That ’70s Show would lead Ashton Kutcher to the top of the box office? During and after his prank show Punk’d, Kutcher was everywhere, including the big screen. His boyish charm and good looks turned into leading man material, making him a perfect fit for the romantic comedies of the 2000s. He starred opposite then-partner Brittany Murphy in Just Married and Tara Reid in My Boss’s Daughter.

Ashton Kutcher really hit his romantic-comedy stride in the late 2000s and early 2010s. He starred in 2008’s What Happens in Vegas… with Cameron Diaz, who was a major draw on her own by then, and 2011’s No Strings Attached opposite Natalie Portman in a rare rom-com role, which likely drew audiences to theaters to see how she fared. In addition to leading his own romantic comedies, Kutcher participated in some of the biggest ensemble films in the genre, including Valentine’s Day, boosting his box-office earnings immensely.

7 Patrick Dempsey

Rom-Com Box-Office $468M

As far back as 1987’s Can’t Buy Me Love, Patrick Dempsey starred in romantic comedies, likely due to his “McDreamy” good looks, put to excellent use on Grey’s Anatomy decades later. However, even after leading Can’t Buy Me Love, Dempsey wouldn’t return to the genre of love until the mega-hit Sweet Home Alabama with Reese Witherspoon in 2002. The film sees a battle of the dimples between Dempsey’s perfectly adequate suitor and Josh Lucas‘ hometown endgame.

After several years of winning hearts and performing surgery on them in Grey’s Anatomy, Disney’s live-action musical Enchanted started a renewed romantic-comedy boon for Dempsey. No longer was he the second choice for the leading lady; he “got the girl” in Enchanted, Made of Honor, and Bridget Jones’s Baby (sort of). Adding to Dempsey’s impressive romantic-comedy box-office earnings is the ensemble piece Valentine’s Day, although he’s a sleaze in that one.

6 Richard Gere

Rom-Com Box-Office $474M

Like Diane Keaton, Richard Gere has expertly shifted his roles in the rom-com genre over the years. Gere started as a leading man in romantic comedies with 1990’s extraordinarily successful Pretty Woman, alongside reigning romantic-comedy box-office queen Julia Roberts. In it, he played the role of a handsome, rich, and lonely businessman who pays for a little romance, and audiences loved him for it. For several years after, Gere stuck to leading dramas, even some romantic ones like First Knight.

In 1999, Gere and Roberts reunited in Runaway Bride, again to great success. This revitalized Gere’s romantic-comedy career with Dr. T and the Women and Shall We Dance? following soon after. While none of Gere’s romantic comedies has hit at the box office quite as well as his Roberts’ collaborations, he deftly transitioned into “older” romance films like Nights in Rodanthe, which reunited him with Diane Lane, and The Second Best Exotic Marigold Hotel. Now, Gere can be seen as the father in romantic comedies like last year’s Maybe I Do.

5 Adam Sandler

Rom-Com Box-Office $475M

While most of Adam Sandler‘s extensive filmography consists of goofy comedies, there tends to be a romantic interest included somewhere in the mix. He’s starred alongside Kate Beckinsale in Click, Patricia Arquette in Little Nicky, Salma Hayek in Grown-Ups, and Fairuza Balk in The Waterboy, to name only a few. However, Sandler sometimes stars in films that highlight the romantic aspect, ably acting as a leading man. For example, Sandler often acts opposite Drew Barrymore. Their first romantic comedy, The Wedding Singer, was a surprising success after more juvenile hits like Billy Madison and Happy Gilmore.

The Wedding Singer became a beloved film for both fans and non-fans of the genre thanks to Sandler’s perfect blend of comedy and heart and impeccable chemistry with Barrymore. So much did the pair enjoy working together, and audiences delighted in watching them, that they reunited for two more romantic comedies: the hopelessly sweet 50 First Dates and the family-driven Blended. Also adding to Sandler’s impressive romantic-comedy box-office earnings is Just Go With It—his first of three successful outings with Jennifer Aniston—and Mr. Deeds, in which he romances Winona Ryder.

4 John Corbett

Rom-Com Box-Office $510M

After his likable series regular gig on Northern Exposure, John Corbett landed the role of Carrie’s earnest love interest, Aidan, on HBO’s Sex and the City, winning a place in many viewers’ hearts. Around that time, he also starred alongside Nia Vardalos in the revolutionary rom-com My Big Fat Greek Wedding, which exploded at the box office due to its grounded and realistic charm and brilliant comedic turns from the large supporting cast.

Corbett’s box-office earnings increased with two My Big Fat Greek Wedding sequels and Sex and the City 2. Impressively, Corbett is among the highest-grossing rom-com actors with only two extremely successful franchises. Adding to his romantic-comedy credentials, but not much to his box-office success, were his roles in Raising Helen alongside Kate Hudson and Serendipity, with leads John Cusack and Kate Beckinsale.

3 Tom Hanks

Rom-Com Box-Office $568M

A staple of romantic comedies in the ’80s and ’90s, Tom Hanks possessed an easy-to-like everyman charm; he’s someone you could realistically meet on the street. Hanks made a Splash on the big screen alongside Daryl Hannah in the whimsical mermaid romantic comedy. Hanks later dabbled in several comedies like Bachelor Party, The Money Pit, and Dragnet before finding superstardom in 1983’s Big.

Ever the versatile performer, Tom Hanks starred in a handful of romantic comedies throughout his prolific career. However, the two standouts and highest-grossing are opposite rom-com queen Meg Ryan. The pair followed up the success of their 1993 film Sleepless in Seattle with another box-office smash in 1998’s You’ve Got Mail. While the former leaned toward the romance and the latter swayed more toward the comedy, both were box-office hits for the stars. Although he mainly does dramas nowadays, Hanks revisited the rom-com genre twice more, in The Terminal with Catherine Zeta-Jones and Larry Crowne with Julia Roberts.

2 Hugh Grant

Rom-Com Box-Office $655M

Surprisingly not the highest-grossing romantic-comedy actor, Hugh Grant has made a very successful career in rom-coms, starting with his breakout role in 1994’s Four Weddings and a Funeral. His floppy hair and roguish grin immediately won over viewers and landed him a leading place in the romantic comedy genre throughout the late 90s and early 2000s. Grant did Nine Months with Julianne Moore before playing Edward Ferrars in Emma Thompson‘s beloved Jane Austen adaptation, Sense & Sensibility. In 1999, Hugh Grant starred with A-lister Julia Roberts in the smash hit Notting Hill, cementing himself as the rom-com king.

The 2000s saw him paired with nearly every rom-com queen there is: Renée Zellweger in Bridget Jones’s Diary, Sandra Bullock in Two Weeks Notice, Drew Barrymore in Music & Lyrics, and Sarah Jessica Parker in Did You Hear About the Morgans? Grant also proved that he can reign supreme among a stacked cast of quality British performers, dancing his way around 10 Downing Street as the Prime Minister in the holiday rom-com classic Love, Actually.

1 Bradley Cooper

Rom-Com Box-Office $686M

Drumroll, please! The current king of romantic comedies is none other than Bradley Cooper…at least according to the box office! Cooper appropriately got his first acting role in an episode of Sex and the City as a brief love interest for Carrie, foreshadowing his successful future career in rom-coms. He didn’t start as a leading man, though, playing the sleazy fiancée to Rachel McAdams‘ Claire in Wedding Crashers, which is his highest-grossing romantic comedy to date.

Following supporting roles in other rom-coms, Cooper took leading turns in flops like All About Steve and Aloha and smaller roles in ensemble pieces like Valentine’s Day and He’s Just Not That Into You. The 2012 film Silver Linings Playbook hit the sweet spot with viewers and critics alike and earned Cooper his first Oscar nomination. Now, Cooper is pulling triple duty, making waves as an actor, director, and even musician, all while voicing one of the best characters in one of the biggest franchises of all time. Hail to the rom-com king, Bradley Cooper.

NEXT: 10 Modern Rom-Com Kings Destined to Become Icons