15 Times Unexpected Actors Played Romantic Roles - And Nailed It

Voting Rules
Vote up the actors who unexpectedly made your heart skip a beat.

There’s an art to playing a romantic lead; just ask Hugh Grant or Kate Hudson. But romance is not singularly for the most beautiful or handsome people in the room. Check out these unexpected actors who played romantic roles and totally nailed it.

James Gandolfini will forever be known for playing violent mob boss Tony Soprano. However, the late actor also starred opposite Julia Louis-Dreyfus in the criminally underrated mid-life romantic comedy Enough Said. Gandolfini’s character is a sweet, cuddly teddy bear of a man. He’s so good in the film that within just a couple of scenes, you can forget it’s the same actor who played a guy who killed his own nephew.

Which other actors unexpectedly made your heart skip a beat with their winning romantic performances?

Photo: MGM/UA Communications Co. / Fox Searchlight Pictures / Universal Pictures

  • Most people know James Gandolfini from his rageful mob boss character Tony Soprano, a once-in-a-lifetime role that earned the actor three Primetime Emmy Awards. But in 2013, the actor played Albert, a middle-aged divorced dad, in Nicole Holofcener's underrated gem Enough Said

    Albert is funny, kind, and sweet - a teddy bear of a man. Holofcener's romantic dramedy depicts what divorced dating is like for middle-aged folks. The film hit the big screen after the actor's sudden death.

    "It's bittersweet, I really wish that he could be here standing next to me," said co-star and onscreen love interest Julia Louis-Dreyfus. “Having said that, though, I think this movie is a celebration of his enormous talent, and it's really a triumph and a lovely thing for his legacy. I'm so proud to have been in this film with him.”

    “You can see his abilities were very deep,” added Louis-Dreyfus. “He was an amazing actor. In fact, this part that he plays is much closer to him than Tony Soprano was, in so many ways, which I think will be nice for his fans to see.”

    36 votes
  • Jack Black exploded off the big screen in 2003's monster hit comedy School of Rock. Black, who is also one-half of the rocking duo Tenacious D, brought intense energy with his over-the-top, in-your-face, shout-out-loud persona.

    After several more comedies including Nacho Libre, Black toned it down considerably in the seasonal rom-com The Holiday. Writer-director Nancy Meyers wrote the role of lovable film composer Miles specifically for Black after seeing him in School of Rock. “When I was thinking of this movie, I thought he was someone I would like to write a part for," said Meyers. “I’m aware he’s not Clark Gable, he’s not tall, dark, and handsome, but he’s adorable, he’s lovable.”

    “It’s my way of saying this is the right kind of guy, this is what most guys look like if they’re lucky, he’s so adorable, and why not?" added Meyers. "Everybody has a heart and deserves to fall in love, and he should get a great girl. So I fixed him up with Kate Winslet."

    60 votes
  • Adam Sandler ruled in 1990s school boy potty humor with his mega-successful financial comedies Happy Gilmore and Billy Madison. The Saturday Night Live alum's raucous brand of comedy stylings satisfied anyone looking for easy laughs and who wondered whether shampoo was superior to conditioner.

    Sandler proved over this prolific career that he's more than just a one-trick pony. In fact, the actor has made a smooth transition to serious starring roles in films like Punch Drunk Love and Uncut Gems. The first time audiences really got to see this other side of Sandler came in the 1998 romantic comedy The Wedding Singer.

    In the hit film, Sandler plays a nice guy wedding singer who gets dumped on his wedding day. The actor starred opposite Drew Barrymore and their onscreen chemistry became immediately apparent.

    Niall Gray from Screen Rant thinks The Wedding Singer is Sandler's best all-around effort. He wrote:

    The Wedding Singer was the first film in which Sandler was really able to display the full range of his talent, and it deserves far better recognition than it gets. Not only is it one of Sandler's more subtle comedic performances, but its romance element is often praised equally. Critically, it's considered one of his best comedies, but unfortunately, it's still largely overlooked during discussions of Adam Sandler's best work, with the conversation more frequently gravitating towards his other '90s hits like Happy Gilmore and Billy Madison.

    40 votes
  • Billy Crystal showed off his impeccable comic timing in the 1970s and '80s in the sitcom Soap and as a standout cast member on Saturday Night Live. “You look maaaarvelous.”

    Hollywood called the funnyman to bring his comedy chops to the big screen with supporting roles in The Princess Bride and Throw Momma from the Train. However, it was the Nora Ephron/Rob Reiner 1989 romantic comedy When Harry Met Sally… that made Crystal a bankable movie star. The film asked the eternal question: "Can men and women ever just be friends?"

    There aren't many perfect movies. However, a case can be made that When Harry Met Sally… is the quintessential romantic comedy. Crystal's onscreen chemistry with Meg Ryan helped to make the rom-com a financial and critical hit. 

    Critic James Berardinelli from Reelviews wrote:

    Casting is one of the film's strengths. It would be hard to imagine anyone other than Billy Crystal as the wisecracking, eternally pessimistic Harry. Crystal's dry style is perfect for this role; he makes Harry insufferable and likable at the same time. And, beneath it all, there beats the heart of a caring man. 

    30 votes
  • Ali Wong  In 'Always Be My Maybe'
    Photo: Netflix

    Ali Wong is known for her honest, raw, and unfiltered work as a standup comedian. She became a household name thanks to two Netflix specials. She also served as a go-to comic for TV shows like Chelsea Lately, Inside Amy Schumer, and Best Week Ever

    Wong worked as a writer on the ABC sitcom Fresh Off the Boat, which is where she met Randall Park. 

    Wong and Park (along with Michael Golamco) wrote the screenplay for the 2019 Netflix romantic comedy Always Be My Maybe. They star as childhood pals who reconnect later in life. 

    The actress brought her personal sensibility to the starring role. Candice Frederick from The Wrap wrote:

    Much of that subversive approach emerges from Wong’s naturally bold personality. If you’ve seen either of her two Netflix stand-up specials, Hard Knock Wife and Baby Cobra, then you already know that she is unafraid of raunchy, bitter, in-your-face comedy. It makes Park’s random straight-dude act all the more amusing because he can vacillate between goofiness (like when Marcus raps about a tennis ball) and earnestness at the drop of a dime. Meanwhile, Wong’s Sasha revels in cutting sarcasm and quick wit.

    29 votes
  • Nicolas Cage has literally done it all on the big screen. He traded faces with John Travolta, stole the Declaration of Independence, and ran through a grocery store with panty-hose over his head trying to steal a package of diapers. 

    However, the Academy Award-winning actor doesn't have many love stories in his filmography. One of Cage's most endearing and underrated turns came opposite Cher's Oscar-winning performance in 1987's Moonstruck

    Cage plays Ronny Cammareri, an opera-obsessed, unhinged, strange dude who blames his brother for his missing hand. 

    Nick L. from Collider wrote:

    All that said, these brilliant performances still can’t hold a candle to the one Cage delivers in Norman Jewison’s Moonstruck: a screwy masterpiece of a New York love story where the actor dives heedlessly into the role of a heartthrob baker whose love for opera matches Cage's own highly operatic register. Cage isn’t just acting here - he’s all but singing to the camera, and it’s impossible not to get caught up in the magnetism of his performance.

    38 votes