A big part of their success - let's be honest here, the reason for their success - was Meg Ryan, the magnetic, funny, and stunning actress who starred in all three movies.
After her first movie role in 1981, the actress remembers job offers "just kept coming," until she was forced to drop out of college to focus on film career.
Along with her classic rom-coms, Ryan starred in box office hits like Kate and Leopold and City of Angels. She even voiced the lead character in Anastasia.
So why does it seem like Meg Ryan disappeared from Hollywood in the early 2000s?
In fact, she did. But first, she was caught up in a tabloid scandal that may have ended her career just as it was at its peak.
Tabloids and gossip magazines had a field day when the actress nicknamed "America's sweetheart" was caught two-timing Quaid with her costar, Russell Crowe.
The fact that Meg and Quaid had an eight-year-old son together only attracted even more tabloid attention.
Ryan retreated from the spotlight following the scandal, and didn't tell her side of the story for a decade.
The Scarlet Woman
Ryan revealed to W that she was treated like "the scarlet woman" in Hollywood after the story broke.
"Oh! I’m having that experience now!” she told the magazine.
Ryan was especially upset by the public reaction to the cheating scandal because she claimed that her marriage to Quaid was basically over when she had the affair.
She has also suggested that the actor was also dating other women at the same time, and that women in Hollywood are held to a different standard than their male costars.
But judging by Ryan's life today, she's not itching to be a Hollywood star again anytime soon.
She's So Over Hollywood
While the bad press from her affair may have ended Ryan's career, that suited the actress just fine.
“I didn’t have to care what people thought," she said about life out of the spotlight.
"I have gotten to do what I guess I secretly wanted to do. Be totally under the radar and live my life.”
While she never really fell "under the radar," Ryan lived a pretty quiet life in New York City.
She was often spotted in public with her on-and-off boyfriend, musician John Mellencamp, and her adopted daughter Daisy True.
As Ryan revealed, she was never comfortable with her image as "America's sweetheart" or "the girl next door."
“It felt … like ideas were being projected onto me that had nothing to do with me,” she remembered.
“The girl next door to what? I never felt like a very conventional person.”
Plastic Surgery Woes
The way the press covered Ryan's plastic surgery also contributed to her choice of living out of the public eye.
To this day, headlines like "What Happened to Meg Ryan's Face?" greet any public appearance she makes.
"I'm old enough to remember when Meg Ryan looked like Meg Ryan," one particularly nasty person wrote on Twitter after her appearance at the 2016 Tony Awards.
For the record, Ryan says comments and criticism about her looks don't bother her. But they're definitely not making her nostalgic for life in the spotlight either.
"I don’t pay a lot of attention frankly,” she said about mean comments on her appearance.
“There’s a lot of hatred in the world today; it’s so easy to judge. Imagine being a hater, how stupid! [The] people I value talk about kids growing up, what kind of world they are going into, what we are eating, what we are breathing.”
Her Life Today
These days, if you see Meg Ryan it probably won't be on the big screen. You're more likely to spot her out and about in Manhattan with Mellencamp or her daughter.
Ryan had no roles between 2009 and 2015 (except in a web series), and has taken just a handful of acting jobs since then.
The actress says she's perfectly happy being out of the “airless bubble of rich Hollywood people," but that hasn't stopped her from making a small comeback.
She'll also be on TV in the new show Picture Paris later this year.
And in the near future? Ryan has hinted at even more career changes as she explores her artistic side.
"I never really defined myself as an actor," she told the crowd at a recent film festival.
"I think at heart I’m a writer. So that was a natural progression for me."
"I got tired of waiting to be chosen," she went on to explain.
"When you’re an actor, you’re a cog. When you produce, you understand the other gears. I’m in first gear now."
She may not be "America's sweetheart" anymore, but Ryan is still happy, healthy, and doing what she loves.
I'll have what she's having!
Which Meg Ryan movie was your absolute favorite?