Andie Anderson (Kate Hudson), a journalist, tries to push a man away for an article, while Ben Barry (Matthew McConaughey) bets he can make a woman fall in love with him. Their conflicting plans lead to hilarious and heartfelt moments. The iconic yellow dress Hudson wears in the film became one of the most memorable fashion moments in rom-com history.

A widowed Italian-American woman (Cher) falls for her fiancé’s passionate younger brother (Nicolas Cage) in a whirlwind romance. Cher won an Academy Award for Best Actress, cementing her status as a Hollywood legend.

A lovable but awkward man (Steve Carell) attempts to lose his virginity with the help of his eccentric friends. The chest-waxing scene was filmed for real, with Carell’s genuine reactions captured on camera.

A runaway princess (Audrey Hepburn) explores Rome with an American journalist (Gregory Peck), discovering freedom and love in the process. Hepburn won an Oscar for her first major Hollywood role, making her an instant star.

A modern retelling of The Taming of the Shrew, this teen rom-com stars Julia Stiles and Heath Ledger in a battle of wits and romance. Ledger’s performance, including his rooftop serenade, helped launch his career.

Two business rivals (Tom Hanks and Meg Ryan) unknowingly fall in love through anonymous online messages. The film was inspired by The Shop Around the Corner (1940) but updated for the internet age.

A fairy-tale princess (Amy Adams) is magically transported to modern-day New York City, where she discovers real-world love. Adams' performance was widely praised, solidifying her as a leading actress, and the film playfully references classic Disney animations.

A charming Brit (Hugh Grant) navigates love and relationships through a series of weddings and a funeral, all while falling for an elusive American (Andie MacDowell). The film turned Grant into a rom-com icon and was one of the highest-grossing British films ever.

A single, self-deprecating woman (Renée Zellweger) navigates love and self-improvement while torn between two suitors. Zellweger gained over 20 pounds and adopted a British accent to fully embody the character.

A wealthy and stylish Beverly Hills teen (Alicia Silverstone) plays matchmaker but realizes she’s clueless about her own love life. The film is a loose adaptation of Jane Austen’s Emma and remains a defining ‘90s classic.

A swashbuckling fairy tale about true love, adventure, and revenge, as Westley (Cary Elwes) fights to reunite with his beloved Buttercup (Robin Wright). The film’s endlessly quotable lines have made it a cult classic.

Over years of friendship, Harry (Billy Crystal) and Sally (Meg Ryan) debate whether men and women can be just friends before realizing they belong together. The famous diner scene featuring Ryan’s fake orgasm was entirely her idea and became one of the most iconic moments in film history.

Toula Portokalos, a 30-year-old Greek-American woman, falls in love with Ian, a non-Greek teacher, much to her traditional family's dismay. As she navigates cultural clashes and family expectations, she learns to embrace both love and her heritage. The film was a surprise box office hit, becoming the highest-grossing romantic comedy of all time at the time, despite having a modest budget of $5 million.

A humble British bookseller (Hugh Grant) falls in love with a famous Hollywood actress (Julia Roberts), leading to a whirlwind romance. The line “I’m just a girl, standing in front of a boy, asking him to love her” became one of the most iconic rom-com quotes.

Childhood friends Monica (Sanaa Lathan) and Quincy (Omar Epps) navigate their love for each other and their passion for basketball over the years. The film was one of the first to blend sports and romance with equal weight.

Josie Geller (Drew Barrymore), a shy journalist, goes undercover in high school to report on teen life but unexpectedly gets a second chance at love and self-confidence. The movie's climactic kiss scene at the baseball stadium is considered one of the most romantic in rom-com history.

A successful but overworked woman (Angela Bassett) finds love and rejuvenation with a much younger man (Taye Diggs) while vacationing in Jamaica. The film introduced Diggs in his first major film role, launching his Hollywood career.

A modern homage to 1960s romantic comedies, this film pits a feminist author (Renée Zellweger) against a playboy journalist (Ewan McGregor) in a battle of wits and attraction. The film’s vibrant retro aesthetic was inspired by classic Doris Day and Rock Hudson films.

When Julianne (Julia Roberts) learns her best friend (Dermot Mulroney) is getting married, she sets out to sabotage the wedding—only to realize she might not be the right person for him. The film’s twist on the traditional rom-com ending made it a standout in the genre.

A cynical weatherman (Bill Murray) is stuck reliving the same day until he learns to change his ways and find love. The film’s time-loop concept has influenced countless movies and TV shows.

A Pakistani comedian (Kumail Nanjiani) navigates love, culture, and a medical crisis when his girlfriend (Zoe Kazan) falls into a coma. The story is based on the real-life romance of Nanjiani and his wife, Emily V. Gordon, who co-wrote the screenplay.

An ambitious worker (Jack Lemmon) lends his apartment to executives for their affairs but falls for his boss’s mistress (Shirley MacLaine). The film won five Academy Awards, including Best Picture, and remains one of the most acclaimed romantic comedies of all time.

A gay Taiwanese man in New York (Winston Chao) stages a fake marriage to appease his traditional parents, leading to unexpected complications. The film was directed by Ang Lee and helped launch his international career.

A widowed man (Tom Hanks) and a journalist (Meg Ryan) fall in love through a radio show, culminating in a fateful meeting at the Empire State Building. The film pays homage to An Affair to Remember (1957), a classic that inspired its storyline.

An African prince (Eddie Murphy) travels to America to find a woman who will love him for who he is, not his wealth. Murphy plays multiple roles in the film, showcasing his legendary comedic versatility.