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10. Knocked Up

Sometimes, the most unlikely stories capture our hearts, and Knocked Up is a perfect example of this. Directed by Judd Apatow, this 2007 romantic comedy stars Katherine Heigl and Seth Rogen as two individuals whose lives take an unexpected turn after a one-night stand results in a pregnancy. The film’s raw humor and heartfelt moments resonated with audiences, making it a massive hit. While it may not be a traditional "hearts and flowers" romance, Knocked Up charmed viewers and raked in an impressive $148,768,917 at the box office. Its opening weekend alone brought in $30,690,990, showcasing the power of a well-crafted, relatable story.

9. Runaway Bride

The timeless chemistry between Julia Roberts and Richard Gere is undeniable, and Runaway Bride is a testament to their on-screen magic. Directed by Garry Marshall, the 1999 film tells the story of a woman notorious for leaving her fiances at the altar and the reporter (Gere) who falls in love with her while uncovering her story. With its whimsical charm and delightful performances, the movie became a box office sensation, grossing $152,257,509. Its opening weekend brought in $35,055,556, further solidifying Julia Roberts’ status as one of Hollywood’s most bankable stars.

8. Sex and the City

The big-screen adaptation of the beloved HBO series Sex and the City was a cultural phenomenon, and its success extended far beyond the screen. Released in 2008, the film reunited Sarah Jessica Parker, Cynthia Nixon, Kim Cattrall, Kristin Davis, and Chris Noth in their iconic roles, bringing Carrie Bradshaw and Mr. Big’s love story to new heights. The movie opened with an impressive $57,038,404 and went on to gross $152,647,258 as of 2025. It wasn’t just a film; it was an event, celebrated by fans worldwide who couldn’t get enough of the fashion, friendship, and famous Manhattan backdrop.

7. The Proposal

In 2009, Sandra Bullock and Ryan Reynolds teamed up for The Proposal, a hilarious and heartwarming rom-com that kept audiences laughing. Bullock plays a high-powered businesswoman who enlists her reluctant assistant (Reynolds) to pretend to be her fiancé to avoid deportation to Canada. The chemistry between the leads, paired with memorable performances from Betty White and Mary Steenburgen, made the film a standout. The Proposal opened with $33,627,598 and eventually grossed $163,958,031, proving that humor and heart are a winning combination.

6. Crazy Rich Asians

The most recent film on this list, Crazy Rich Asians (2018), broke box office records while breaking cultural barriers. Based on Kevin Kwan’s bestselling novel, the story follows Rachel Chu (Constance Wu), an economics professor who travels to Singapore with her fiancé, Nick (Henry Golding), only to discover he’s from one of the wealthiest families in the country. Directed by Jon M. Chu, the film was a critical and commercial success, showcasing Asian representation in Hollywood. It opened with $26,510,140 and went on to gross $174,532,921. Its impact extended beyond the screen, paving the way for more diverse storytelling in mainstream cinema.

5. There’s Something About Mary

The Farrelly brothers’ 1998 comedy There’s Something About Mary is a quirky, raunchy, and unexpectedly endearing film that became a cult classic. Starring Ben Stiller and Cameron Diaz, the story revolves around a man who hires a private investigator to track down his high school crush, only for things to take a series of bizarre turns. With its outrageous humor and memorable performances, the film captivated audiences, grossing $176,484,651 during its run. Its opening weekend brought in $13,740,644, but word-of-mouth ensured its long-term success.

4. Pretty Woman

Julia Roberts and Richard Gere once again proved their box office magic with Pretty Woman, a 1990 romantic comedy directed by Garry Marshall. The story of a businessman who falls for a charming sex worker he hires for the week is a modern-day fairy tale that tugged at heartstrings worldwide. The film opened with $11,280,591 and went on to gross $178,406,268 during its theatrical run. It became a defining film of the genre, cementing Roberts’ status as a leading lady and leaving an indelible mark on pop culture.

3. Hitch

Will Smith stars as a "date doctor" in the 2005 romantic comedy Hitch, a story about a man who helps other men win the hearts of their crushes. His expertise is put to the test when he falls for a reporter (Eva Mendes) determined to expose him. The film’s witty dialogue and heartfelt moments made it a crowd-pleaser, grossing $179,495,555. Its opening weekend brought in $43,142,214, showcasing Smith’s ability to command the box office with his signature charm.

2. What Women Want

Nancy Meyers’ 2000 romantic comedy What Women Want delivered a fresh take on love and understanding. Mel Gibson stars as a chauvinistic advertising executive who gains the ability to read women’s minds after an accident. The film explores themes of feminism and self-discovery while staying true to its comedic roots. It opened with $33,614,543 and went on to gross $182,811,707, becoming a timeless favorite for audiences.

1. My Big Fat Greek Wedding

No oneexpected My Big Fat Greek Wedding to become the surprise hit of 2002, but its heart, humor, and relatability won over audiences worldwide. Written by star Nia Vardalos, the film tells the story of a Greek woman who falls in love with a non-Greek man and the cultural hilarity that ensues. Made on a budget of just $5 million, the film opened with $597,362 but went on to gross a staggering $241,438,208, making it the highest-grossing romantic comedy on this list. Its success is a testament to the power of authentic storytelling and the enduring appeal of love and family.