The delight of Nia Vardalos' My Big Fat Greek Wedding is that it's actually multiple films rolled into one. Comedy! Romance! What a culture shock! Windex's undiscovered healing abilities! Vardalos' homage to Greek culture in all its beauty and frustration centers on her heroine, Toula, and her struggle to persuade her family to accept her non-Greek lover, Ian (played by John Corbett). It's the epitome of a frolic, with bizarre individuals and their absurdist perspectives on life flowing out of every scene. Each character is given so much individuality and attention that My Big Fat Greek Wedding might be divided into multiple sequels based on the antics of Aunt Voula (a rib-achingly comic Andrea Martin) or the headstrong Gus (Michael Cera).

My Big Fat Greek Wedding might be broken into multiple offshoots following the antics of Aunt Voula (a rib-achingly comic Andrea Martin) or the headstrong Gus (Michael Constantine), who can trace anything and everything back to Greece. But it's the romance, which Vardalos writes so beautifully, that holds everything together. Following Toula and Ian's romance from the moment they first laid eyes on one other until Ian's personal proposal. A film of this scope and scope requires an anchor, which these two provide admirably.

Detailed information:
Directed by: Joel Zwick
Starring: Nia Vardalos, John Corbett, Lainie Kazan, Michael Constantine, Gia Carides, Louis Mandylor
Release date: April 19, 2002
Running time: 94 minutes

Only in the rom-com to end all rom-com would you have Andie Anderson and Benjamin Barry as leads. How to Lose a Guy in 10 Days is just as frothy as it sounds from the outset—a film about a Cool Girl before the word became popular, whose chemistry with a little chauvinistic man's man is irresistible even if their romance is doomed from the start. She's a writer at a women's magazine seeking to carve out a place where she can write about important subjects—which, for the time being, necessitates ensnaring a man and torturing him to the point of breaking up with him. Meanwhile, he is only attempting to demonstrate that he can make any lady fall in love with him.

Kate Hudson and Matthew McConaughey sold their characters with wit and flair, thoroughly immersing themselves in the roles while delivering some lines with just a smidgeon of cynicism. Andie had taken "Benny Boo-Boo... Boo-Boo-Boo" to a Céline Dion concert by the conclusion, and he has dragged, brought—her to Staten Island to meet his family after just a few days of dating. Yet, after they kiss and make up on the bridge after a genuinely embarrassing karaoke battle in front of everyone they know, it's nearly difficult not to applaud.

Detailed information:
Directed by: Donald PetrieCrazy Rich Asians (2018)
Starring: Kate Hudson, Matthew McConaughey, Adam Goldberg, Michael Michele, Shalom Harlow
Release date: February 7, 2003
Running time: 116 minutes

Rachel Chu (Constance Wu), a Chinese-American professor of economics, is Chinese-American, and the adaptation of Kevin Kwan's best-selling novel Crazy Rich Asians emphasizes this fact constantly. Rachel's college closest friend Peik Lin (an exuberant Awkwafina) refers to her as a "banana": "Yellow on the surface, white on the inside," with a superlative attached. When Rachel's mother (Tan Kheng Hua) learns she would be visiting her handsome boyfriend's family in Singapore, she reveals her an unsettling truth: "You are Chinese, you speak Mandarin, but you are American in here," she continues, pointing to Rachel's heart.

It's a bittersweet, but perceptive observation, one that finely articulates Rachel's compounded sense of otherness throughout the film, especially once the plot gets going and Rachel realizes her debonair Nick Young (Henry Golding) is the son of an obscenely wealthy Singaporean family that leans heavily on traditional Chinese family values and matriarchy. She is middle-class, was raised by a single mother, and is, as everyone has pointed out, Chinese-American.

If Crazy Rich Asians is not as incisive in its satire of the bourgeoisie as one might wish in a cultural landscape where it has become more popular to be vocally anti-capitalist (or, at the very least, skeptical of capitalism as a system and ideology), it still sparkles in its in-jokes about Asianness and Chinese families and the interconnectedness of other Asian people. It is slickly directed by Chu, whose skill in crafting champagne on a beer budget rests not in the goods on show in and of themselves, but in the color correction and cinematography by Vanja Cernjul.

Detailed information:
Directed by: Jon M. Chu
Starring: Constance Wu, Henry Golding, Gemma Chan, Awkwafina, Nico Santos, Lisa Lu, Ken Jeong
Release date: 7 August, 2018
Running time: 120 minutes

In a genre that demands ever more inventive obstacles to its protagonist's ultimate destination, Garry Marshall's Overboard relies on one that may make modern audiences uncomfortable—a rich woman (Goldie Hawn) with amnesia who is duped into believing she is the wife and mother of a guy (Kurt Russell). There's a lot of "positioning" going on to make things more appealing.

Hawn's pre-amnesia character is so dislikeable that her real husband pretends not to recognize her after the accident once he realizes she's lost her memory, and she stiffs Russell's handyman after a job well done—but the plot is ultimately powered by the chemistry and comic timing of its leads, not whether a viewer believes there's a consent problem. This version (as opposed to the 2018 picture starring Anna Farris) it deserves a position on this list simply because Hawn and Russell make it work.

Detailed information:
Directed by: Garry Marshall
Starring: Goldie Hawn, Kurt Russell, Edward Herrmann, Katherine Helmond, Roddy McDowall
Release date: December 18, 1987
Running time: 112 minutes

The reason why Peyton Reed's sleeper masterpiece, starring Renée Zellweger and Ewan McGregor, wasn't well-received when it was released in 2003. The film is an unapologetic confection, candy-coated to the point of creating cavities and too rich in wink-wink allusions to the Doris Day films that inspired it. Down with Love was a difficult sell in the wake of an impending Iraq War; it couldn't have appeared more frivolous. But all of that candy was merely a cover for what's actually at stake here, which is a rewrite of cinematic romances and their continuous sex wars.

The picture, about a famous writer's proto-feminist quest to convince women to live and love on their own terms and the magazine writer attempting to tear her down, is devoid of cynicism. But its characters do: these are individuals who understand the strategic intricacies of romance and spend a whole film outdoing one other. It all leads up to one of the best moments in Zellweger's acting career (which is saying a lot): a heart-stopping monologue about the things a woman would do simply to be acknowledged by the guy she loves. At the heart of all this nonsense is a heroine who deserves a happy ending—but not at the price of the newfound freedom she instills in others.

Detailed information:
Directed by: Peyton Reed
Starring: Renée Zellweger, Ewan McGregor, David Hyde Pierce, Sarah Paulson, Tony Randall
Release date: May 9, 2003
Running time: 102 minutes