29+ Secrets From Famous Rom-Coms of the 1990s and 2000s Revealed


| LAST UPDATE 04/12/2022

By Kayla Black

During the 1990s and 2000s, rom-coms dominated Hollywood and became fan-favorites around the globe. But behind the scenes, things weren't so picture perfect. We're looking back at some secret stories from the decades' top flicks.

Freddie's Tears On Set in 'She's All That'

She's All That, which came out in 1999, quickly took theaters by storm. Many believe it's one of Hollywood's greatest teen rom coms, and made such a lasting impact on pop culture that it inspired a spin-off starring Addison Rae!

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Fans of the film may remember the iconic scene where Laney faces Zack, and demands to know, "Am I a f**king bet?" And according to Rachael Cook, Freddie Prinze Jr. struggled with the scene. "He was kind of emotional," Cook admitted. Apparently, the powerful scene made Prinze "choke up" when seeing his co-star burst!

Off-Screen Romances in '10 Things I Hate About You'

When 10 Things I Hate About You came out in the spring of 1999, it instantly became a cult classic amongst teens and adults. From the iconic scenes to the stellar soundtrack, fans of the romantic comedy were fawning over the Shakespearean adaptation and one up-and-coming actor in particular: Heath Ledger.

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Heath and Julia Stiles played hard-headed lovers, but the sparks were flying both on and off the set. The pair were rumored to have dated, with the actress saying her late co-star was "a very powerful, lovely human being." Looks like Heath meant it when he sang Can't Take My Eyes Off You on the bleachers!

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Authentic Locations in 'How to Lose a Guy in 10 Days'

Upon its release in 2003, How to Lose a Guy in 10 Days earned big bucks across movie theatres around the world. The rom-com struck the hearts of viewers as they watched Andie and Ben fall in love. And while they might have entered their relationship with ulterior motives, other aspects of the film were really authentic.

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For example, Andie's magazine, Composure, was actually set at the Conde Nast building, where the iconic Vogue publication is based. And as part of her prep to prepare for her role as a journalist, Kate Hudson shadowed Vogue's editor, Anna Wintour, for the day. Talk about getting into character!

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Script Criticisms in 'American Pie'

Based on Eugene Levy's steady performance throughout the whole American Pie franchise, it could be seen as a surprise that the comedian actually had a number of problems with his character in the lead-up to the first film! That's right, Eugene thought his character was "creepy."

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The accomplished actor sat down with Huffington Post to revisit his earlier role and his troubles with the original script. "When we started that movie, I didn’t really like the part the way it was written," Levy explained. In order to make his character more "square," Eugene ended up improvising on-camera. It certainly worked!

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Doppelgängers in '13 Going on 30'

13 Going on 30 has remained one of Hollywood's most iconic rom-coms of the early 2000s. And even after 15-plus years, most fans of the flick will recall just how good of a job the casting crew did of hiring an actress that resembled a young Jennifer Garner. And apparently, looks were all that mattered!

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Columbia Pictures/Revolution Studios via IMDb

According to Insider, Christa B. Allen was hired to play a young Jenna without any acting experience. She was picked by the team solely based on her striking resemblance to the star, Garner. But the doppelgänger status served Allen well. She went on to play Jennifer as a teenager in Ghosts of Girlfriends Past in 2009!

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Family Affairs in 'Knocked Up'

Knocked Up's creator, Judd Apatow wanted to make a rom-com that touched on the real ups and downs of parenthood. And what better way to touch on such a personal topic than to hire his own family to star in the film? He wanted to cast his daughters to act alongside their mom, but what did his wife, Leslie Mann think?

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She was pretty hesitant to include their daughters Maude and Iris. "Time passed by, and I was saying no, no. no, and then I’m like - I dunno, maybe," Mann told Collider. "And then it was like a week before and he said, 'You have to tell me now…' Then it ended up just happening." The girls ended up starring in This is 40, too!

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Sarah Jessica Parker's Pad in 'Hitch'

Following the release of Hitch back in 2005, the cast and crew were fairly honest about the "all hands on deck" method in creating the film. The stars were encouraged to riff and improvise on set, which resulted in some of the most iconic scenes in the entire movie. But what about Will's famous lesson on 90/10 kissing?

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According to Hitch's director, Andy Tennant, Will pitched the door-step scene while they were strolling around New York. It seemed like the perfect fit, so they started going door to door to find a place to shoot. And guess who opened up? None other than Sarah Jessica Parker. The famous scene is filmed on the actress' steps.

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Lucy's Cure in '50 First Dates'

The whole plot of Peter Segal's 50 First Dates rests on Drew Barrymore's character and the amnesia she suffered from following a tragic car accident. But not many knew that the director toyed with the idea of "curing" her at the end of the film. So, did Segal regret the choice of ending?

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"The studio debated, should Lucy be cured and it be a happy ending? And I’m so glad everyone supported this bittersweet ending because that’s what was so heartbreaking about it, that she has to re-experience this every day," Segal said. "I think that’s part of the charm and heartbreak of it."

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Hollywood Feuds in 'Cinderella Story'

At the time of Cinderella Story's release, Chad Michael Murray was one of Hollywood's most iconic teenage rom-com actors in the game. And when he joined the cast, Hillary Duff couldn't help but feel butterflies. "I definitely had a crush on him," Duff later shared with Cosmopolitan.

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But the casting choices also came with drama for Hillary. "[Lindsay Lohan] got pissed off because I worked with Chad Michael Murray [on Cinderella] after she had worked with him," Duff told Blender. "She called [Chad] up and said all these awful things about me." Keep scrolling for more secret stories from these iconic rom-coms!

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Manifesting the Part in 'The Devil Wears Prada'

After a successful but restricting run in children's films such as The Princess Diaries and Ella Enchanted, Anne Hathaway was desperate to snag a role in a more sophisticated project. So safe to say that she was showing her enthusiasm for the part of Andy in some not-so-subtle ways.

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In an interview following the film's 10th anniversary, Anne told Variety that upon meeting with the film's producer, Carla Hacken, she left a little message in her office. The eager actress traced "hire me" into the sandbox of the producer's zen garden. Well, it worked out, didn't it?

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Questionable Casting Choices in 'Clueless'

We're "totally bugging" over this behind-the-scenes movie fact from the 1995 rom-com, Clueless. While most diehard lovers of the iconic film might not be able to imagine the endlessly quotable production any other way, there were many back and forths during the casting stage. Who almost didn't make the cut?

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Well, Alicia Silverstone had the role of Cher in the bag. According to E! News, Paul Rudd almost missed out on the role of Josh to Ben Affleck and Jeremy Renner. And the role of the loveable stoner nearly went to Owen Wilson. Plus, the part of Cher's BFF was read by 90s hip-hop sensation, Lauryn Hill!

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Authentic Moments in 'Princess Diaries'

Speaking of Anne, fans certainly fell in love with her for her quirky and oh-so-relatable portrayal of an awkward teen-turned-princess in the Disney film. But it turns out some of that adolescent clumsiness wasn't written in the script at all, it was just an authentic Anne Hathaway moment! Remember her tumble on the bleachers?

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In a later interview with TV Guide Trailers, Anne shared the secret behind the scene. "I turned really fast, slipped on a puddle [and] just absolutely fell, and burst out laughing and kept going with the scene," she said. And while Anne guessed it would be cut out, to her surprise it was in the trailer six months later!

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Quadruple Threats in 'The Wedding Planner'

By the time that The Wedding Planner came out in 2001, J-Lo had already established a name for herself as a force to be reckoned with in the industry. Between her successful singing career and her numerous stints in Hollywood, J-Lo was a shoo-in for the role of Mary Fiore in the romantic comedy, and her co-star agreed.

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In honor of the film's 10th anniversary, Lopez and McConaughey rehashed some of their favorite memories from their film. And after all these years, Matthew had nothing but respect for J-Lo's rigorous work ethic. He called her a "quad-threat" for her commitment to doing her own stunts in the film!

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Lingering Hopes for '27 Dresses'

So far, we've learned celebrities that almost snagged the roles from these iconic rom-coms from the 1990s and 2000s, but what about films that barely made it to theaters? 27 Dresses writer Aline Brosh McKenna had an interesting movie fact to share with fans when speaking to Decider.

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In the early days of the film, the rom-com project was nearly adapted for television rather than cinema. And according to the writer, she'd still like to see the project on TV! Despite the lingering wish, McKenna said she was happy overall with the outcome of the film starring Katherine Heigl.

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Legal Troubles in 'Bring It On'

Most of us remember Bring It On for its iconic choreography routines and endlessly quotable lines. And with a cast filled with young and up-and-coming talent, you might imagine that the sets were high-energy places. But, as it turned out, the youthful spirit got out of control and landed some stars in prison during filming.

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According to the film's executive producer, Max Wong, Jesse Bradford, and Eliza Dushku among others "were on the beach drinking and got arrested and got thrown into a Mexican jail." In an MTV piece, Dushku wanted to set the story straight: "I got us out of it and there was no producer bailing out happening," she clarified.

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Special Permissions in 'Sweet Home Alabama'

Ready for more secrets behind some of Hollywood's most iconic romantic comedies? Well, for fans of Reese Witherspoon's Sweet Home Alabama, it won't come as much of a surprise that part of the successful film was filmed in New York City. But what few knew was just how special the locations in the metropolis were...

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Touchstone Pictures/Original Film via IMDb

Sweet Home Alabama is believed to be the first movie filmed in the Big Apple following the attacks on 9/11. It was a huge honor for the cast to work in the wounded city, and they went on to film scenes in the exclusive Tiffany's location - the first movie to do so since Breakfast at Tiffany's!

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First Kisses in 'What a Girl Wants'

In the early 2000s, Amanda Bynes was one of Hollywood's "it girls," having taken the industry by storm in Nickelodeon's shows and Big Fat Liar. But behind all the success was just a young teenager who was spending her pivotal years on set and in front of the camera.

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And for Amanda, that meant experiencing some firsts while filming. When working on What a Girl Wants, it was believed that Bynes had her first kiss! The film's director spilled the deets, adding "Amanda really loved him." And the chemistry between these two young actors was undeniable!

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Stagefright in 'My Best Friend's Wedding'

The 1997 romantic comedy My Best Friend's Wedding was a landmark release for a number of reasons. And for Cameron Diaz, it was the role of a lifetime. The young actress was fairly new on the Hollywood scene, and actually had the film's star, Julia Roberts, to thank for joining the cast!

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But according to Cameron, she wasn't as thankful to have joined when it came to the iconic karaoke scene. "That was some acting," Diez admitted. "But I allowed the true terror of singing in front of people to be alive in me." Lucky for her, her authenticity stole the show.

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Embarassing Moments in 'There's Something About Mary

Speaking of Cameron Diaz and getting embarrassed, her later project, There's Something About Mary, brought more awkward moments for the rom-com star. We've got two words for you: hair gel. Ring any bells? Well, chances are Cameron Diaz still remembers the scene like it was yesterday, and she had big problems with it.

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While they were on-set, Cameron was really concerned that the filmgoers would be too focused on her weird hair-do to focus on the funny dialogue. But as soon as she saw audience members crack up at the premiere, all those worries were put to bed. Keep scrolling for more interesting movie facts...

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Humiliating Scenes in 'Notting Hill'

When Notting Hill came out in 1999, Emily Mortimer was a fairly new name on the scene. In fact, according to IMDb, it was only the fourth project of her entire career. Her role as Will's "perfect girl" rebound lasted no more than a couple of moments on the screen, but Emily, unfortunately, made a lasting impression.

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PolyGram Filmed Entertainment/Working Title Films via IMDb

She got an allergic reaction to fabric and was covered in hives on set. "It was a nightmare," she told PeopleTV's Couch Surfing. "Everybody was really embarrassed! It was very awkward. It was like, 'who is this girl who's come - she's just got one scene and she's making such a meal of it.'" Yikes!

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Acting Dilemmas in 'High Fidelity'

Besides a stellar soundtrack, Stephen Frears's 2000 directorial project, High Fidelity, was known for John Cusack's intimate monologues. For those not familiar with the cinematic film, the method of a movie character talking directly to the audience is known as "breaking the fourth wall." And Cusack was not down to try it.

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In 2000, the film's star confessed to The New York Times about his hesitations. "I vetoed that idea. I thought there'd just be too much of me," he said. It took some convincing from the movie's director, Frears, to build John's confidence to the point where he was willing to give it a try.

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Battle Wounds in 'Miss Congeniality'

The year 2000 was a busy one for romantic comedies! That same year, Sandra Bullock starred in the legendary rom-com, Miss Congeniality. The film went on to be a huge success in the box office and has quotable moments that are still referenced in today's pop culture. But it wasn't all fun and games on set...

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In one of the earlier scenes at the FBI training center, Benjamin Bratt and Bullock were wrestling. And while filming, things got a little too rough. "It was the scene where they kind of roll into a position, and [Bratt] stopped it with, 'Oh, my God! You got my testicles!'" the director recalled of the comical moment.

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Mommy Duty in 'Legally Blonde'

Legally Blonde is still one of the most beloved rom-coms of all time. And part of what made the 2001 film such a fan-favorite was Reese's energy. But in reality, the Reese was a tired new mom. "Some nights Ava would wake up screaming…and then [I had] to be on the set at 7 in the morning for make-up!" she told Cinema.com.

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"And then you throw in the fact that I'm supposed to be playing a very bubbly and energetic California preppy who is smiling all the time! I kept thinking, 'I'm going to kill myself! I'm never going to make it!'" Want to learn more secret stories from your favorite rom-coms? Keep scrolling...

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Motherly Help in 'My Big Fat Greek Wedding'

My Big Fat Greek Wedding went on to be the highest grossing rom-com of all time, according to E! News, and the cast and crew knew that they'd created something lovable and authentic. So authentic, in fact, that in the true spirit of the film, the star's mother gave her two cents about the lines. Classic, right?

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"[My mother] gave me a line for the movie the other day," Nia Vardolas said before filming started. "I have the father in the movie say, 'I am the head of this house'... [And] my mother suggested I have the mother character reply, 'But the woman is the neck and she can turn the head any way she wants.'"

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Fake Swimming in 'Love Actually'

In the years following the 2003 release of Love Actually, the film's director, Richard Curtis, had tons of secrets to share from behind-the-scenes. And hats off to the actors, because they sure did a good job convincing us with their acting skills, even if the conditions weren't exactly ideal.

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StudioCanal/Working Title Films/DNA Films via IMDb

For example, the lake where Colin Firth and Sienna Lúcia Moniz frollic was actually ridiculously shallow. "No one inspected the depth of the lake, so you see them sort of lying around pretending to be swimming," he told Montclair Film. Apparently the actors had to bend on their knees and do some serious faking!

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Harsh Reactions in 'Forgetting Sarah Marshall'

Romantic comedy mastermind Judd Apatow came back in 2008 to bring his creative genius to a new film: Forgetting Sarah Marshall. The film had all the tell-tale signs of an Apatow creation, including his cast regulars and some funny, but cringey, scenes. And the mother of one star wasn't so impressed...

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Apatow Productions via IMDb

In a 2014 interview with Vanity Fair, Jason Segal confessed that his nude scene didn't go over well with his mom. "She cried," he admitted. And she followed up by sending warning emails to all her family members before they headed to the theater to check it out. Sorry, Mrs. Segal!

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"Deep Depression" in 'She's the Man'

Back when Amanda Bynes starred in She's the Man in 2006, it felt like nearly every teenager in America flocked to the theaters to catch the hilarious rom-com remake of the Shakespearean classic, Twelfth Night. But for Amanda, the film wasn't anything close to a success. In fact, she fell into a "deep depression."

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In a tell-all interview for Paper Magazine in 2018, Amanda admitted that seeing herself dressed as a man was "a super strange and out-of-body experience." "It just really put me into a funk," Bynes confessed. We're not done yet! Keep scrolling for more...

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Over-Commitment in 'Bridget Jones's Diary'

When Renée Zellweger was cast in the 2001 romantic comedy, Bridget Jones's Diary, she caused quite the uproar. Apparently, people in the United Kingdom doubter her ability to accurately portray an authentic British accent for the entire film. Little did they know, Zellweger was giving it 110%.

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According to her interview in The New York Times, Renée was accidentally using the accent after-hours. "I'd call my boyfriend and he couldn't take it," she admitted. Luckily her co-stars understood. "They knew I wasn't some geek trying to sound English. They knew it was part of the job."

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Hidden Clues in 'Enchanted'

With all the musical numbers and outrageous outfits in Enchanted, it was hard for viewers to focus on anything going on in the background. But according to the film's director, Kevin Lima, there were some secrets sprinkled throughout for loyal Disney fans.

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Need proof? The restaurant that Dempsey and Adams eat at, Bella Notte, is named after the song from Lady and the Tramp. Also, the pizza that they share had a Mickey Mouse face crafted out of peppers! This movie might warrant a re-watch just to catch these sneaky clues.

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Audience Mockin in 'Four Weddings and a Funeral'

Remember the pivotal romantic scene from Four Weddings and a Funeral? Charles, played by Hugh Grant and Carrie, played by Andie MacDowell finally shared the kiss that we had been waiting for the whole film. But unfortunately, some of the magic was ruined by one of Andie's lines...

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"Oh... Is it still raining?" was ripped apart by fans. But MacDowell came to her character's defence when speaking with The Daily Mail. "The character was so in love, she wasn’t thinking about the fricking rain," she said. "I think perhaps it was raining a bit hard for the line. But that wasn’t my fault!"

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Double the Work in 'The Parent Trap'

When The Parent Trap came out in 1998, the film catapulted Lindsay Lohan to new levels of fame and sealed her deal as a Disney princess for many years to come. And to be fair, she certainly earned her praise fair and square due to some lacking technology on set.

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Because CGI wasn't what it is today, the cast of The Parent Trap had to film scenes with the twins together two times: once with Lindsay Lohan playing each twin with a stunt double filling in for the other part. "We did everything twice," Elaine Walter told Today. Luckily, it resulted in some lifelong friendships on set.

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Painful Improv in 'The 40-Year-Old Virgin'

Consider this your warning, this one might hurt just to read... But one thing's for sure, Steve Carell gave it 100% in the waxing scene from The 40-Year-Old Virgin. Ring any bells? What about "Oh the humanity!"? Despite all of Hollywood's tips and tricks, Steve opted for the real deal for his character...

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And that meant actually waxing his chest for the scene. But take it from Carell, he explained it on a Rove Live appearance. "See how red my chest is? Now if you look really closely in the middle, you can see blood pooling right there," he explained. "I have such respect for women for being able to do that."

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Battle Wounds in 'Bride Wars'

The 2009 romantic comedy Bride Wars was full of verbal brawls and petty comments, but maybe the most iconic scene was when Liv and Emma finally duked it out on the aisle and fought in front of all their guests. And apparently, Kate Hudson got a little caught up in the moment while filming.

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"We were really tired, and I had this big rock on my finger... I whacked Annie in the face so hard," Kate confessed on the Rachael Ray show. "Two hours later, she's sitting in the back of a car with an ice pack on her face. I was so bad. I really clocked her!"

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Authentic Moves in 'Mamma Mia!'

When the first Mamma Mia! came out in 2008, it brought ABBA's disco tunes back to life and gave Meryl Streep another legendary film to add to her list. And she certainly poured her youthful energy into the movie, even at the age of 59 years old when it was underway! But apparently, Streep can do anything!

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Even if that means doing the splits in mid-air! She later explained her motivations when speaking to The Guardian. "I just did the splits on instinct," she told the publication. "As an actor, you're not allowed to think." And it certainly wowed the audience.

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Chatter Boxes in 'The Holiday'

With a cast as large and as impressive as that in The Holiday, it wouldn't be hard to imagine that there were some funny industry stories shared on set. But apparently, one cast member, in particular, loved to relive some Hollywood highlights from his golden years... Even if that meant delaying the production team.

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The director, Nancy Meyers, remembered it fondly. "[Eli Wallach was] so funny of anecdotes that sometimes we had to say: 'Eli, just let us get this take!'" she laughed. "The problem is that everyone was so interested in him… There are so many stills on this movie of Eli sitting in a chair and all of us around him."

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City Landmarks in '(500) Days of Summer

When director Marc Webb created his indie romantic comedy (500) Days of Summer, he planted loads of small details to help the story develop and make for a worth re-watch. One of those elements was the bench that Summer and Tom frequent throughout their turbulent relationship.

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The bench wasn't just a prop: it was part of LA's Angels Knoll, and it became quite the tourist hot spot after the film came out. Unfortunately, recent reports show that the park's fate is just as grim as Summer and Tom's. The area has been fenced off and is set to be developed by 2028.

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Talent Shows in 'Made of Honor'

Patrick Dempsey certainly took fans by surprise when he ditched his scrubs and traded them in for a kilt in the 2008 romantic comedy Made of Honor. And while fans eventually got used to seeing him in a lighter setting, many were certainly surprised when they saw McDreamy juggling in the film!

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But no stunt-double here! Dempsey did the whole thing himself. "I started off as a juggler," the actor explained. "I went to the International Juggler's Competition in '83 and was second place in the junior division." Casual! And according to Patrick, the film's director opted to throw in some of his talents into the scene.

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Stripped-Down Cast in 'Eurotrip'

For those who have seen the raunchy 2004 romantic comedy titled Eurotrip, chances are that you may remember the flick for its over-the-top scenes and inappropriate comedy. But, after all, some argue that its R-rated approach was what made it such a classic. Remember the nude beach scene?

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Well, the original script had way less nudity in it. But according to the film's writer David Mandel, his team just thought, "wouldn't it be funnier if it was just wall-to-wall penises?" And according to the film's star Michelle Trachtenberg, the film's extras were down with the program and stripped down immediately!

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Industry Rivals in '17 Again'

By the time that 17 Again came out in theaters back in 2009, Zac Efron was a force of nature in Hollywood. Besides his Hairspray dynasty, he'd also went on to star in Hairspray. So it surprised many to learn that his nemesis in this romantic comedy was actually an industry rival in real life, too!

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That's right, Hunter Parrish was a rival on and off the set. He had come close to snagging to the role of Troy in HSM before backing out. "It was down to five guys and then I got offered a part in this amazing Robin Williams movie... I heard a rumor that I was their favorite, but I never made it to the end," he told GQ in 2009.

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Slap-Happy in 'Monster-in-Law'

Tensions were flaring in the 2005 romantic comedy Monster-in-Law. And it all came to a boiling point during the infamous fight scene between Jennifer Lopez and Jane Fonda's characters. But behind the scenes, J-Lo was worried. "I was so afraid to hit Jane Fonda in the face or hurt her in any way," she told Making a Scene.

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And unfortunately, it came with some battle scars. "My nail went up into her eye," Lopez admitted. "I was mortified. I was just like, 'I'm so sorry!" And she was like, 'It's fine, it's fine!'… She didn't care. She's such a gangster b***h." Luckily there was no bad blood between the two. "I just love her," Jeniffer said.

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