WORST: I Love Trouble
We had more chemistry with the frog we were forced to dissect in science class than Roberts shared with her leading man Nick Nolte in this 1994 bomb written by Nancy Meyers. And it makes sense given that the co-stars did not get along.
"From the moment I met him we sort of gave each other a hard time, and naturally we get on each other's nerves," Roberts told The New York Times in 1993. She went on to note that while Nolte could be "completely charming and very nice," she added, "He's also completely disgusting. He's going to hate me for saying this, but he seems go out of his way to repel people. He's a kick."
Nolte later returned the favor, telling The Los Angeles Times, "It's not nice to call someone 'disgusting. But she's not a nice person. Everyone knows that."
Trouble indeed!
Mother's Day
It's never a good sign when the biggest talking point about a movie is one of the star's wigs. And yet that was the case when it came to Roberts' distracting red bob in this 2016 ensemble helmed by the late Garry Marshall, who directed the star in Pretty Woman. It was later revealed to be the fake hair she wore in Notting Hill (while her character, a world-famous actress, was playing an astronaut in the fake film Helix) that Roberts held onto.
Sadly, while we can recall the bright wig in vivid detail, we couldn't tell you Roberts' storyline in this movie if you offered us $3 million, which is how much she made for her four days of work on Mother's Day.
Valentine's Day
Roberts ditched the wig for her second go-around in one of Marshall's star-studded holiday outings, but that doesn't mean she fared much better in this 2010 movie. She is partnered with Bradley Cooper for their vignette about two strangers who connect on a plane and the big reveal at the end is that he's gay. (We've had worse Valentine's Days, TBH.)
The Mexican
You know how some people believe that if two beautiful people procreate their child will be unattractive? Well, this 2001 action-adventure rom-com is the movie star version of that as Roberts combined forces with Brad Pitt to deliver a product that was no bueno.
Larry Crowne
Roberts and Tom Hanks, two rom-com legends, came together for this 2011 movie, which was directed and co-written by Hanks. And while they had an easy, natural connection, there just wasn't much there there, kind of like a cake without frosting.
America's Sweethearts
Starring Roberts, John Cusack, Catherine Zeta-Jones and Billy Crystal, this rom-com carried high expectations ahead of its 2001 release. But critics were less than sweet on the film, despite its meta commentary about Hollywood and high-maintenance movie stars. And the problem seemed to be not enough romance or comedy, with the top tier level of talent even proving unable to rise above the fluff.
Ticket to Paradise
Is the plot—a divorce couple coming together to stop their daughter from getting married—revolutionary? Of course not. But no mere mortal can resist the combined charisma, charm and screen presence of Roberts and her BFF George Clooney and their banter is a one-way ticket to paradise.
Runaway Bride
Maybe we should whisper this, but we secretly prefer this Roberts-Richard Gere movie to their much-more beloved collaboration—which we will be getting to in a minute—for several reasons: 1. The adorable small town setting and side characters, including scene-stealer extraordinaire Joan Cusack! 2. Seeing all of the fun weddings Maggie (Roberts) sprinted away from! 3. The delicious banter between Roberts and Gere! Aren't. We. Right?
Alas, we can begrudgingly acknowledge that there is a certain spark missing, something Gere admitted to feeling while making the 1999 film.
"Whatever that magic was in the first movie, you can't make that happen," he told Entertainment Weekly. "While there's some wonderful stuff in the movie, it certainly didn't have the magic of the first one. The expectation that it was going to have that same kind of delicious magic was irresponsible. It was a different movie, it was a different time."
Mystic Pizza
Oh, how we love this 1988 coming-of-age movie that served as Roberts' first major role, two years before her big break as Vivian in Pretty Woman. But her star power is fully on display as the impulsive and emotional waitress Daisy, who engages in a star-crossed romance with a yuppie. But, while their relationship is cute (and the scene where Daisy douses his fancy car in fish water is one of the movie's most memorable moments), it is the friendship between the three young women that really can't be topped.
My Best Friend's Wedding
Okay, let's just get it out of the way: Roberts' character Julianne, who decides she is in love with her best friend only after he gets engaged to someone else, is actually The Worst in this 1997 gem. And yet, it also proves the choke-hold the star has on all of us that we are still upset she—spoiler alert!—!doesn't get the guy in the end, a refreshing change to the genre's usual formula.
Pretty Woman
Not ranking this loose retelling of Cinderella this high on a list of Roberts' best rom-coms? Big mistake. Huge! Listen, we are aware that the relationship between prostitute Vivian and wealthy businessman Edward (Gere) is problematic and we are 96 percent sure the couple broke up, like, one week after the movie ends. Still, you simply cannot take your eyes off of Roberts, who won the Golden Globe for Best Actress in a Musical of Comedy after her star-making turn in the 1990 classic. And she was right, she treated us so nice that we never let her go.
BEST: Notting Hill
We're just an E! News team, standing in front of a reader, asking them to recognize the pure and utter magic of Roberts' tour de force performance in this 1999 classic. At the peak of her charisma and charm and combined with the irresistible allure of Hugh Grant, there is a reason Notting Hill remains one of Roberts' most enduring movies.