When Movies Met Meg Ryan
Meg Ryan’s best romantic comedy likely was her very first one: When Harry Met Sally (1989), but she’s made some really good films since then. And, well, not to break your heart or anything, she’s also made some not-so-great ones too. Here we’ll rank them, from worst (least best?) to greatest.
My Mom’s New Boyfriend (2008)
In the US, this weakest of Meg Ryan’s rom coms went straight to DVD, and may have helped drive Ryan from show biz for a decade and a half.
Millennium Films, My Mom's New Boyfriend (2008)
My Mom’s New Boyfriend (2008)
Called by one critic an “unmitigated disaster,” My Mom’s New Boyfriend casts Ryan as the mother of an FBI agent played by Colin Hanks, eldest son of Tom Hanks, so at least there’s a sense of the circle completing itself somehow.
Millennium Films, My Mom's New Boyfriend (2008)
My Mom’s New Boyfriend (2008)
The convoluted plot of My Mom’s New Boyfriend requires the Hanks character to spy on his mother, which would account for why the movie is titled My Spy in parts of the world. The FBI thinks the boyfriend is an art thief, which is appropriate, as you may feel this movie robbed your time and attention.
Millennium Films, My Mom's New Boyfriend (2008)
My Mom’s New Boyfriend (2008)
Antonio Banderas plays the suspected thief, first meeting Ryan’s character when his toy helicopter knocks her in the head. Viewers may have wished a similar fate for themselves, if it would help them forget this dubious production.
Millennium Films, My Mom's New Boyfriend (2008)
Addicted To Love (1997)
In an earlier effort, Ryan teamed up with Matthew Broderick to play a couple pretending to date each other to make their exes jealous. In reality, this movie may make you jealous of anyone watching just about any other film (aside from My Mom’s New Boyfriend).
Warner Bros., Addicted to Love (1997)
Addicted To Love (1997)
Although not the worst on this list, Addicted To Love could be the perfect medicine for anyone wanting to cool their enthusiasm for the genre.
Warner Bros., Addicted to Love (1997)
IQ (1994)
And whose brilliant idea was it to include Albert Einstein in a rom-com? Although Walter Matthau is adorable in his own way playing the world’s most famous scientist, does it really take a genius to pair up Ryan’s grad student and Tim Robbins’ plain-old mechanic?
IQ (1994)
Rogert Ebert loved Walter Matthau and gave the film 3½ stars out of 4, but most critics marked it lower down on the bell curve, with Rotten Tomatoes calculating a 45% score on its tomatometer.
What Happens Later (2023)
So, after the underwhelming My Mom’s New Boyfriend, what happens later after that 15-year break from a movie release? Well, how about pairing up Meg Ryan and David Duchovny?
Prowess Pictures, What Happens Later (2023)
What Happens Later (2023)
Critics did feel there was some detectable chemistry between the leads, but for a rom-com, there was a definite deficit in the romance and/or comedy department.
Prowess Pictures, What Happens Later (2023)
What Happens Later (2023)
Nonetheless, it was nice to see a more adult version of Ryan on screen.
Prowess Pictures, What Happens Later (2023)
Kate & Leopold (2001)
Einstein would likely be appalled by the science and logic of this time-travel movie, as Ryan and Hugh Jackman take “romance for the ages” a little too literally.
Miramax, Kate & Leopold (2001)
Kate & Leopold (2001)
Jackman stars as confused Duke Leopold, who finds himself propelled to modern-day New York. Of course he bumps into Ryan’s Kate, and romance with the requisite obstacles ensues.
Miramax, Kate & Leopold (2001)
Kate & Leopold (2001)
Despite the nonsensical plot—and an ending that seems to come out of nowhere—there’s a certain charm in this pairing of Ryan and Jackman, so Kate & Leopold makes for a relatively pleasant way to pass the time.
Miramax, Kate & Leopold (2001)
French Kiss (1995)
Apparently, Paris isn’t romantic enough for Meg Ryan’s character until she flies there to win back her fiancé, who’d phoned to say he’d fallen in love at a conference.
Twentieth Century, French Kiss (1995)
French Kiss (1995)
Fellow passenger Kevin Kline sneaks a purloined diamond necklace into Ryan’s purse, somehow knowing she won’t get searched. He needs to sell the necklace to regain the family vineyard.
Twentieth Century, French Kiss (1995)
French Kiss (1995)
Ryan’s character tries to win back her husband, only to realize maybe the thief has stolen her heart instead.
Twentieth Century, French Kiss (1995)
French Kiss (1995)
Critics were ambivalent about French Kiss, but some noted the opposites-attract kind of chemistry between the two leads, with Kline’s over-the-top performance particularly noted.
Twentieth Century, French Kiss (1995)
Prelude To A Kiss (1992)
This is a rom-com without the com, but at least deliberately so, as Alec Baldwin and Meg Ryan play newlyweds whose lives are turned upside down by an old man whose kiss does a Freaky Friday on Ryan’s character.
Twentieth Century, Prelude to a Kiss (1992)
Prelude To A Kiss (1992)
Based on a stage play, some critics loved this tale of switched identity, while others hated it. One critic said Ryan was “almost too adorable for words,” while another wrote that a “leaky Love Boat rerun” would be better viewing.
Twentieth Century, Prelude to a Kiss (1992)
Joe Versus The Volcano (1990)
It’s Meg Ryan versus Tom Hanks in their first film together, though better things were to come. Even if audience reaction wasn’t explosive, there was a certain electricity in the air.
Warner Bros., Joe Versus the Volcano (1990)
Joe Versus The Volcano (1990)
Joe Versus The Volcano also features Hanks’ first cinematic encounter with the South Pacific, a decade before Cast Away. Suffering from a terminal disease, Joe is hired by a nasty mining magnate to jump into a volcano, thereby appeasing local natives. Naturally, he encounters Ryan’s character and gets diverted from this task.
Warner Bros., Joe Versus the Volcano (1990)
Joe Versus The Volcano (1990)
More precisely, Ryan’s third character. The plot of Joe Versus The Volcano, already bubbling over with implausibility, is further strained by the fact that Ryan plays three characters, fortunately including Joe’s main love interest, or it wouldn’t really be a Meg Ryan rom-com.
Warner Bros., Joe Versus the Volcano
Joe Versus The Volcano (1990)
Critics of the film were divided. Roger Ebert gave the movie 3½ stars out of 4, and later wondered why he hadn’t given it a full four stars. On the other hand, Vincent Camby said despite the talent behind the Joe Versus The Volcano, the “grim evidence on the screen” showed how much it just didn’t work out.
Warner Bros., Joe Versus the Volcano (1990)
Sleepless In Seattle (1993)
And now we come to the last three movies in this list, with titles that immediately evoke timeless images of Ryan. We’ll start with Sleepless In Seattle.
TriStar, Sleepless in Seattle (1993)
Sleepless In Seattle (1993)
Ryan and Hanks reunited for this heartwarming tale of two people getting closer and closer, yet only ever meeting right at the end. Early on, studios considering Sleepless In Seattle balked at the very idea of two romantic leads almost never being on screen together.
TriStar, Sleepless in Seattle (1993)
Sleepless In Seattle (1993)
Nora Ephron co-wrote and directed the film, which was originally conceived as a romantic drama before Ephron was hired to rewrite the script for Sleepless In Seattle—and eventually given the job of directing it.
TriStar, Sleepless in Seattle (1993)
Sleepless In Seattle (1993)
Critics had varying reactions, some loving the film and the two leads’ performances, and others finding the whole setup contrived. Nonetheless, Sleepless In Seattle has stood the test of time, fondly nestled in our collective pop-culture memories.
TriStar, Sleepless in Seattle (1993)
You’ve Got Mail (1998)
This film reuniting Ephron, Ryan, and Hanks featured lots and lots of emails, and might have you tearfully recalling the endless CDs of the time begging you to stick them into your computer to sign up for AOL, unless you’re mercifully too young to remember.
Warner Bros., You've Got Mail (1998)
You’ve Got Mail (1998)
Hanks’ Joe Fox runs a bookstore chain that could bankrupt an independent store run by Ryan’s Kathleen Kelly. Naturally, Kelly has some strong thoughts about Fox, who in turn gives her advice by email using a pseudonym, hence the ubiquitous “You’ve got mail” announcements ringing out in AOL’s chirpy electronic voice.
Warner Bros., You've Got Mail (1998)
You’ve Got Mail (1998)
So, unlike Sleepless In Seattle, the two leads in You’ve Got Mail do find themselves in the same room at times, even if Fox hides behind his online identity throughout much of the movie.
Warner Bros., You've Got Mail (1998)
You’ve Got Mail (1998)
Ironically, product placement is prominent in a movie about a small business fighting a big chain for survival. Besides the obvious AOL references in You’ve Got Mail, Kathleen’s favorite coffee shop is a Starbucks.
Warner Bros., You've Got Mail (1998)
You’ve Got Mail (1998)
While noting the ironies, critics generally found much of You’ve Got Mail charming, with Roger Ebert noting the “immensely lovable” main characters. But critics were even more charmed by the last film on our list, coming from those ancient days when people met without exchanging emails or emojis.
Warner Bros., You've Got Mail (1998)
When Harry Met Sally… (1989)
“I’ll have what she’s having,” comes the classic line in this classic rom-com, as Ryan’s character, Sally, rises to the challenge of matching funny man Billy Crystal’s Harry in antics and intensity.
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
A great supporting cast, including Carrie Fisher and Bruno Kirby, helped to complete the mood.
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
Nora Ephron wrote the script, while Rob Reiner directed this film about love and life set mostly in New York City. Ephron based Harry on Reiner and his life after divorce, and she used her own life, and that of her friends’, as inspiration for Sally.
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
In the story, Harry and Sally meet repeatedly over the years, and finally either profess their love to each other or they don’t (far be it for me to spoil the ending of this classic rom-com!).
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
The movie made rom-com history largely thanks to one infamous scene. The now-iconic diner scene in which Ryan’s character loudly fakes a climax in a crowded diner might never have been. The shocking scene was all Ryan’s idea. However, she may have regretted it—they had to do multiple takes.
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
Critics were generally wowed, with some noting the chemistry between Ryan and Crystal, even if the characters of Harry and Sally came across as maybe a little shallow. But there’s no dismissing the deep laughs in this classic comedy which doubles as a classic rom-com, and a classic Meg Ryan performance.
Castle Rock, When Harry Met Sally... (1989)
When Harry Met Sally… (1989)
So yes, it’s a little sad that Ryan’s best rom com was her first, but once you set such a high standard, do you really have to keep on proving yourself? Just imagine how many performers would love to have Meg Ryan’s career as they think, “I’ll have what she’s having!”
Castle Rock, When Harry Met Sally... (1989)
