From You’ve Got Mail to When Harry Met Sally: 7 of the best Meg Ryan romantic comedies

Meg Ryan

Credit: Getty

Film


From You’ve Got Mail to When Harry Met Sally: 7 of the best Meg Ryan romantic comedies

By Jess Bacon

2 years ago

6 min read

After a 14-year hiatus, the queen of romcoms, Meg Ryan, is set to return to the romantic comedy in What Happens Later. To celebrate, here’s a reminder of her seven best romantic comedies…      


In the 1990s, Meg Ryan ruled the romantic comedy. With thick knits, quick wits and effortlessly styled hair, Ryan became the epitome of the modern American woman searching for love… and not settling for anything less.

From her own modern take on Pride & Prejudice’s Elizabeth Bennet in You’ve Got Mail to her long-standing collaboration with Nora Ephron after the success of When Harry Met Sally, Ryan’s films have gone down in romcom history and garnered a cult classic status afforded to very few others.

Now, after a 14-year hiatus from the genre, Ryan is back at the helm of a romcom that she stars in, co-wrote and produced. Need we say more?

Ryan plays Willa, who is snowed in at a local airport and happens to run into her ex-boyfriend, Bill (David Duchovny). After decades apart, the duo reconnect and explore what could have been and what might still be between them…

The trailer set our hearts a-flutter with a long-lost optimism for modern dating and chance meetings, as it promises the “cheeky magic of Ryan’s romcoms of the 90s”.

What Happens Later is released on 3 November in the US, with a UK release date still to be confirmed.  

To get into the spirit while we wait for the Ryanaissance, it’s time to revisit some of Meg’s best romantic comedies. 

When Harry Met Sally

Meg Ryan and Billy Crystal in When Harry Met Sally

Credit: Columbia Pictures

It’s a romantic comedy that needs no introduction. When Harry Met Sally remains one of the best romantic comedies of all time and Ryan’s most famous work. 

For those of you yet to witness this masterclass in the slow-burn romance, Billy Crystal stars alongside Ryan as two Chicago graduates who are thrown together in a long car journey to New York City. 

Yet, it isn’t love at first sight. Instead, the duo don’t get along, but life keeps bringing them back together again. Over time and after a few fake orgasms at lunch, love blossoms. 

It marked Ryan’s first collaboration with Nora Ephron who wrote and directed the cult classic in 1989. When Harry Met Sally is a witty, smart take on modern love that remains timelessly relatable. 

Where can I watch When Harry Met Sally? It’s available to stream now on Amazon Prime. 

You’ve Got Mail

You've Got Mail: Tom Hanks and Meg Ryan in a scene from "You''ve Got Mail."

Credit: Getty

It’s hard to believe that this book-ish enemies-to-lovers romance turns 25 this December, as You’ve Got Mail remains as enchanting as ever. 

Back in 1998, Ryan and Tom Hanks starred as rival bookstore owners Kathleen Kelly and Joe Fox. Corporate businessman Joe is not phased when Fox Books opens a new store just a block away from Kathleen’s independent bookstore, Shop Around the Corner. That is until he realises that ShopGirl, the woman he’s been emailing, is actually Kathleen. 

It’s a charming classic that comes into its own every autumn and is as much a tribute to New York as it is to finding love in the most unlikely of places. Ephron’s movie was ahead of its time for its representation of digital dating, though I’m not convinced as many great love stories will be written about Hinge and Bumble. 

Where can I watch You’ve Got Mail? It’s available to stream now on Netflix. 

Sleepless In Seattle

Sleepless in Seattle

Credit: Sony Pictures

In 1993, we all gave a collective sigh and fell head over heels in love with Tom Hanks as Sam Baldwin and his son, Jonah (Ross Malinger). 

Jonah calls in to a radio show as he’s worried about his grieving father, whose wife Maggie has recently died. Cue, one of the most heartbreaking lines about loss: “Well, I’m gonna get out of bed every morning… breathe in and out all day long. Then, after a while I won’t have to remind myself to get out of bed every morning and breathe in and out… and, then after a while, I won’t have to think about how I had it great and perfect for a while.” 

Annie (Ryan) cries as she hears his voice over the radio, and is more moved and emotionally invested in Sam, after this one interview, than she is in her own partner, Walter (Bill Pullman). 

Even 30 years later this film about love, loss, and life-altering encounters offers a heart-warming message of second chances and finding love when you least expect it. 

Perhaps it hasn’t aged as well in places – Annie stalks Sam across the country and appears at his house – but everything works out in the end because it’s the movies! They get their face-to-face meeting at the Empire State Building and another epic love story is born. 

Where can I watch Sleepless in Seattle? It’s available to stream on NOW. 

Kate & Leopold

Meg Ryan and Hugh Jackman? In a time-travel romance? Sign us up. Kate & Leopold is a 2001 fantasy film that sees a physicist Stuart (Liev Schreiber) accidentally bring his great-great-grandfather Leopold (Jackman) from the 19th century into the present. 

Upon his arrival in this strange, modern world of New York, Leopold stumbles across Stuart’s ex-girlfriend, Kate (Ryan). In an unusual turn of events, Leopold is fascinated by this ambitious career woman and falls in love with her. With his departure on the horizon, Kate and Leopold have a decision to make. Can their love conquer time? Or will they be parted for good? 

The ending is predictable, but we do have some questions about Kate dating her great-great-grandson… 

Where can I watch Kate & Leopold? It’s available to stream on NOW. 

Addicted To Love

This is Meg Ryan’s villain era, as she enters the world of revenge and romantic comedies in the ilk of The Other Woman. In Addicted To Love, Ryan stars as Maggie, who has just discovered her partner had an affair with Sam’s (Matthew Broderick) wife. 

Sam and Maggie connect in their heartbreak and decide to work together to ruin the lives of their traitorous exes. Their revenge scheme consumes their time and eventually leads to a connection between the two of them. 

Though it didn’t garner much commercial or critical success, it’s an entertaining watch that delves into the inevitable ups and downs of romantic relationships. 

Where can I watch Addicted to Love? It’s available to rent on Amazon Prime. 

I.Q.

In 1994, Meg threw a curveball in her romantic-comedy formula when she played science whizz Catherine, who just so happens to be Albert Einstein’s niece. 

Though it’s one of the wackier instalments in her filmography – that sees mechanic Ed (Tim Robbins) fall in love with her while Einstein himself steps in to help educate him (yes, really) – Ryan is as charming and delightful as ever. Stephen Fry also makes an appearance, which rounds off the unique blend of this romantic comedy. 

Where can I watch I.Q.? It’s available to stream on Amazon Prime. 

Joe Versus The Volcano 

The lesser-known Tom Hanks and Meg Ryan collaboration was also their first, in 1990’s Joe Versus The Volcano

The film follows Hanks as Joe Banks, a dying man who is offered a large sum of money to spend his final days in luxury. The catch? When his time is up, he has to jump into a volcano. Yeah, it’s an unusual one. Ryan tags along for this wild ride as three different characters: DeDe, Angelica and Patricia.  

Though it doesn’t boast any major part in romantic comedy history, it did sow the seeds of chemistry between Ryan and Hanks that would go on to define the genre later in Sleepless In Seattle and You’ve Got Mail

Where can I watch Joe Versus the Volcano? It’s available to rent now on Apple TV+. 

Images: Getty; Columbia Pictures

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