Top 20 Rom Coms: The Last 25 Years

In Part One of this list of Top 20 Rom Coms, we explored the origins of the genre, its first 50 years from 1934 – 1984. Now we complete the list with the best of the last 25 years. See how things have changed, or stayed the same (that all important chemistry between the leads!), and let us know what you think in the comments below!




Working Girl – 1988

I have a head for business and a bod for sin. Is there anything wrong with that?

What it’s about: When a secretary (Melanie Griffith) has her idea stolen by her boss (Sigourney Weaver), she seizes an opportunity to steal it back, teaming up with an investment broker (Harrison Ford) and pretending she has her boss's job.

Why it’s great: Mike Nichols’ Working Girl is a perfect 80s rom-com. As Roger Ebert explained of its plot: “the problem with working your way up the ladder of life is that sometimes you can't get there from here.” The story still resonates today, and compliments the great performances, including baby-voiced Griffith’s breakout role.

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When Harry Met Sally... 1989

I came here tonight because when you realize you want to spend the rest of your life with somebody, you want the rest of your life to start as soon as possible.

What it’s about: Harry (Billy Crystal) and Sally (Meg Ryan) have known each other for years, and have become great friends, but they fear sex would ruin the friendship.

Why it’s great: For me, When Harry Met Sally... is the perfect romantic comedy, and another personal favourite. It’s not just the ever-essential chemistry between the leads, which Ryan and Crystal have to spare; the movie covers all the rom-com musts with a true originality, converging perfectly: the witty script, the lovable “best friends” (Bruno Kirby, Carrie Fisher), the real stakes and conversations about relationships between men and women, and the grand gesture at the end. Perfect.

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Say Anything... – 1989

What I really want to do with my life - what I want to do for a living - is I want to be with your daughter. I'm good at it.

What it’s about: A noble underachiever (John Cusack) and a beautiful valedictorian (Ione Skye) fall in love the summer before she goes off to college.

Why it’s great: Let’s face it, every girl wants a Lloyd Dobler, and John Cusack’s superb portrayal of the passionate and honest high school graduate in Say Anything... leaves us in no doubt of his love for Ione Skye’s Diane. Peter Gabriel never sounded so good.

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Pretty Woman – 1990

I appreciate this whole seduction thing you've got going on here, but let me give you a tip: I'm a sure thing.

What it’s about: A ruthless businessman (Richard Gere) needs an escort for some social events, and hires a beautiful prostitute (Julia Roberts). They take a liking to each other and he offers her money if she'll stay with him for an entire week.

Why it’s great: Pretty Woman started what would become a slew of rom-coms throughout the 1990’s. Perhaps none is more famous than this, the launching pad for Hollywood sweetheart Julia Roberts and her mega-watt smile. A classic in the genre.

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Sleepless in Seattle – 1993

Destiny is something we've invented because we can't stand the fact that everything that happens is accidental.

What it’s about: The son of a recently-widowed man (Tom Hanks) calls a radio talk show in an attempt to find his father a partner. Newspaper journalist Annie (Meg Ryan) becomes infatuated with his story.

Why it’s great: Meg Ryan and Tom Hanks are terrific, and the tribute to the classic “An Affair to Remember” is perfectly evoked in this Nora Ephron gem. Playing at our ideas of destiny and fate, Sleepless in Seattle is romance in its most precious form.

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Four Weddings and a Funeral – 1994

A toast before we go into battle. True love. In whatever shape or form it may come. May we all in our dotage be proud to say, "I was adored once too."

What it’s about: Following the fortunes and various weddings (and a funeral) of a group of London friends, Charles (Hugh Grant) thinks he's found "Miss Right" in Carrie (Andie MacDowell), an American.

Why it’s great: I cannot watch Four Weddings and a Funeral without wishing Charles had just ended up with his bestie Fiona (Kristin Scott Thomas). That’s the power of Four Weddings… it’s very, very British, and so it follows that we’d want our main man to end up with the girl that, well, he doesn’t. Bucking trends, it’s the friends in this film that provide the real romance and comedy.

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My Best Friend’s Wedding – 1997

Getting what you deserve is totally unfair.

What it’s about: When Julianne’s (Julie Roberts) long-time friend (Dermot Mulroney) announces his engagement to another woman (Cameron Diaz), she realizes she loves him herself, and sets out to get him with only days before the wedding.

Why it’s great: My Best Friend’s Wedding stars the queen of the rom com, Julia Roberts, and has probably one of the most satisfying “didn’t get the get the girl/guy” endings in movies. Instead, Julia ends up with her gay best friend George (Rupert Everett). So much more rewarding than the original ending, which had her with another potential boyfriend.

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10 Things I Hate About You – 1999

Who needs affection when I have blind hatred?

What it’s about: A remake of the classic Shakespeare play "The Taming of the Shrew” set in a modern day high school.

Why it’s great: Starring the late Heath Ledger in his first big American role, 10 Things I Hate About You is a clever adaptation of Shakespeare’s classic. Julia Stiles is a true original, playing the part of Kat as though the Bard had her in mind when he wrote the prickly part, and she and Ledger have chemistry to burn.

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Bridget Jones’s Diary – 2001

It is a truth universally acknowledged that when one part of your life starts going okay, another falls spectacularly to pieces.

What it’s about: A single woman (Renee Zellweger), determined to improve herself as a New Years resolution, keeps a diary while struggling with her feelings for her caddish boss (Hugh Grant) and a disagreeable acquaintance (Colin Firth).

Why it’s great: Bridget Jones’s Diary is a modern classic, based on Helen Fielding’s bestseller. The imperfectly perfect Bridget, played with confidence and fantastic humour by Zellweger, quickly became a modern day heroine. With Grant and Firth along for the ride, the movie has real wit and pathos, while maintaining all the personality of the book. Who hasn’t had a Bridget moment?

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50 First Dates – 2004

I've never even met you.

What it’s about: Henry (Adam Sandler) meets Lucy (Drew Barrymore), and thinks he's finally found the girl of his dreams, until he discovers she has short-term memory loss and forgets him the very next day.

Why it’s great: Like many a good rom com pairing, Sandler and Barrymore have worked together several times now, both maintaining a warm and truthful screen presence when they team up. 50 First Dates and its Hawaiian setting are delightfully romantic and, although unlikely and also featuring Rob Schneider, holds up to repeat viewings.

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The Proposal – 2009

Margaret, will you marry me? Because I'd like to date you.

What it’s about: A pushy boss (Sandra Bullock) forces her assistant (Ryan Reynolds) to marry her in order to keep her Visa status in the U.S. and avoid deportation to Canada. To keep up the ruse, they head to Alaska to meet his family.

Why it’s great: Bullock and Reynolds seem like a new, hot rom com pairing. Both are wonderful in The Proposal, a heart-felt and genuinely funny addition to the genre. Reynolds has perfect comic timing, and Bullock’s screen presence must be the envy of her peers.

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