A massive hit that defined 90s gross-out comedy, this film follows Ted (Ben Stiller) who hires a private investigator (Matt Dillon) to track down his high school crush, Mary (Cameron Diaz), only for both men, and several others, to become obsessed with her. Directed by the Farrelly Brothers, the humor is often outrageous and pushes boundaries, but it's grounded in a central, albeit twisted, romantic pursuit. While perhaps less purely 'cute' than others on this list due to its edgier gags (like the infamous hair gel scene), its undeniable cultural impact and central romantic quest make it a notable entry in the broader comedy landscape.

Katherine Heigl stars as Jane, a woman who has been a bridesmaid 27 times but struggles to find her own happy ending. Things get complicated when her younger sister falls for the man Jane secretly loves, and a cynical wedding columnist (James Marsden) starts following her story. The film hits all the classic rom-com beats, featuring a likeable lead, a charming love interest, and plenty of wedding-related humor. The karaoke scene where Jane and the columnist sing "Benny and the Jets" is a particular highlight, showcasing the fun chemistry between Heigl and Marsden.

While primarily a coming-of-age story, this film has enough romantic elements and light-hearted charm to fit the list. Directed by Garry Marshall, it stars Anne Hathaway in her breakout role as Mia Thermopolis, a shy San Francisco teenager who discovers she is heir to the throne of a European principality. Her transformation is guided by her estranged grandmother, the regal Queen Clarisse Renaldi, played by the legendary Julie Andrews. The film is full of sweet moments, comedic mishaps, and the journey of Mia finding her confidence, with a touch of teenage romance along the way.

This romantic comedy adds a supernatural twist to the genre. Reese Witherspoon plays a workaholic doctor who is in a coma, while Mark Ruffalo plays the architect who moves into her apartment and discovers her 'spirit' is still there. Initially at odds, they must figure out what happened to her while developing an unexpected connection. The film blends romance, comedy, and a touch of fantasy, relying on the chemistry between Witherspoon and Ruffalo to sell the unique premise. It's a sweet story about second chances and finding love in unexpected circumstances, set against the backdrop of San Francisco.

Sandra Bullock plays a high-powered book editor facing deportation to Canada. To keep her visa, she strong-arms her assistant (Ryan Reynolds) into a fake engagement. The two must then travel to Alaska to convince his eccentric family (including the hilarious Betty White) that they are truly in love. The film thrives on the comedic dynamic between Bullock and Reynolds, who share witty banter and physical comedy. Watching the uptight editor try to fit in with his quirky family provides many laughs, making it a fun watch powered by its lead actors' charm.

Kate Hudson and Matthew McConaughey star in this battle-of-the-sexes comedy with a high-concept premise. She's a journalist writing an article on how to drive a man away in 10 days, and he's an advertising exec who's bet he can make any woman fall in love with him in the same timeframe. Their conflicting goals lead to hilarious misunderstandings and escalating comedic antics. Hudson and McConaughey have great on-screen chemistry, making their contrived setup surprisingly enjoyable. The film is pure early 2000s rom-com fun, complete with iconic fashion moments like Hudson's yellow dress.

Jennifer Garner shines in this charming fantasy rom-com about a 13-year-old girl who wishes she was 30 and wakes up to find her wish has come true. Navigating the adult world of magazines and careers with a teenage perspective provides plenty of comedic opportunities. The film benefits greatly from Garner's enthusiastic performance and her chemistry with Mark Ruffalo, who plays her childhood best friend. It's a feel-good story about staying true to yourself and appreciating what truly matters, featuring a fun 80s-infused soundtrack and a memorable dance sequence to Michael Jackson's "Thriller".

The first pairing of Adam Sandler and Drew Barrymore in a romantic comedy, and it's a nostalgic trip back to the 1980s. Sandler plays Robbie Hart, a wedding singer who's been left at the altar, and Barrymore is Julia Sullivan, a waitress engaged to the wrong guy. Their friendship blossoms amidst feathered hair, shoulder pads, and classic 80s tunes. The film is full of heart, humor, and great callbacks to the era, including cameos and musical numbers. It's a sweet story about finding love when you least expect it, set to a fantastic soundtrack.

Adam Sandler and Drew Barrymore reunite for their second romantic comedy, this time with a unique premise: a man falls for a woman who suffers from short-term memory loss, requiring him to make her fall in love with him anew each day. Set against the beautiful backdrop of Hawaii, the film finds a sweet spot between Sandler's signature humor and a genuinely touching love story. Their chemistry is undeniable, making the daily courtship feel both funny and romantic. The supporting cast, including Sean Astin and Rob Schneider, adds to the comedic charm.

This film manages to be both incredibly funny and surprisingly heartfelt. It follows a middle-aged man (Steve Carell) whose life unravels after his wife (Julianne Moore) asks for a divorce. He seeks advice from a smooth-talking ladies' man (Ryan Gosling), who teaches him how to pick up women, leading to hilarious and unexpected consequences. The film boasts incredible chemistry among its cast, including Emma Stone in a role that solidified her status as a leading lady. Its witty script offers genuine surprises and moments of emotional depth alongside laugh-out-loud comedy.

Another delightful film penned by Richard Curtis, this movie pairs the charmingly awkward Hugh Grant with America's Sweetheart, Julia Roberts. He plays a humble bookstore owner in the Notting Hill neighborhood of London, whose life is turned upside down when a world-famous actress walks into his shop. The film leans into the fantasy of an ordinary person falling for a superstar, navigating paparazzi, cultural differences, and personal insecurities. It's full of funny situations, endearing supporting characters (like Rhys Ifans' Spike), and that classic Curtis blend of humor and romance. Roberts' famous line, "I'm just a girl, standing in front of a boy, asking him to love her," is delivered with perfect vulnerability.

This ensemble romantic comedy from writer-director Richard Curtis weaves together multiple interconnected stories of love in its various forms, all set during the frantic weeks leading up to Christmas in London. Featuring a star-studded cast including Hugh Grant, Emma Thompson, Colin Firth, Keira Knightley, and Alan Rickman, among many others, the film offers a mix of humorous and poignant vignettes. While not every storyline lands the same way for everyone, the sheer volume of charm, holiday cheer, and feel-good moments makes it an annual favorite for many.

A beloved late-90s gem that cleverly updates Shakespeare's 'The Taming of the Shrew' for a high school setting. This movie launched the careers of several stars, including Julia Stiles, Joseph Gordon-Levitt, and the utterly charismatic Heath Ledger in his breakout American role. Set against the backdrop of the quirky Padua High, the film balances witty banter with genuine heart. Ledger's unforgettable grand gesture on the bleachers, serenading Stiles, is a highlight and perfectly encapsulates the movie's sweet but rebellious spirit. It's smart, funny, and boasts a fantastic soundtrack.

Widely considered one of the greatest romantic comedies ever made, this film is a masterclass in sharp dialogue and character chemistry. Written by the legendary Nora Ephron and directed by Rob Reiner, it follows the titular characters over twelve years, exploring the age-old question: can men and women truly be just friends? Billy Crystal and Meg Ryan have an undeniable spark, delivering lines that have become iconic. The film's structure, punctuated by interviews with older couples recounting their love stories, adds a unique charm. It's a warm, witty, and timeless look at friendship evolving into something more.