Ten Years Later: 15 Behind-The-Scenes Secrets From The Set Of "27 Dresses"

27 Dresses — a groundbreaking romantic comedy that hit theatres in 2008 — is now celebrating its ten-year anniversary! As such, it is only necessary to contribute a list of crazy facts that some fans might not have known went down behind the scenes. Making movies is a tough business, one that people seldom get into and succeed at without the help of many other talented individuals. From writers to directors to actors and producers— it takes a big team to make the dream happen.

Luckily for this cast and crew, they worked efficiently and happily as a team. While there may not have been and crazy drama behind the scenes — there certainly was a lot of laugh out loud moments, close calls, some major changes to the storyline and scenes that almost didn't come to pass. Fans from all over the world enjoyed, and still continue to enjoy the film — with many men admitting the film to be their guilty pleasure. Women often view the movie as a message of hope, true love, the power of speaking one’s mind, and the reality that dreams can and do come true given a little time. So without further ado, here are 20 Crazy Details Behind The Making Of 27 Dresses.

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20 This All Happened In Real Life


Every great film must first be rooted in an equally great idea — and in Aline Brosh McKenna’s instance, the idea behind the iconic rom-com was first inspired by real-life events. Aline says it was her friend Kate who inspired her to get out the keyboard and write the first draft — with Decider reporting how Kate was always (and still is) forever a bridesmaid but never the bride. Aline explained that her friend — instead of marrying a mysterious wedding reviewer — chose to promote herself from bridesmaid to performing the ceremonies. As Aline’s friend has always reportedly been a people pleaser, the idea for Jane’s character wasn’t that far off from real life.

19 The Not-So-Happy Ending

Katherine Heigl

Originally, Aline Brosh McKenna hadn't planned the joyous occasion we see at the end of 27 Dresses. Instead of marrying Kevin, Jane’s fate had been set to remain single and discover her own worth without having to have a man in her life. Aline admitted in Decider that ultimately, she would have liked to give off the impression that Jane would end up with the perfect guy for her, but that she first needed to realize who she was as a person and come to love and embrace the woman she was. The idea was scrapped, however, when Fox agreed to make the movie with Anne Fletcher as the director.

18 Girl Power


Before people really started to voice their opinions on the lack of women in power in the Hollywood scene, 27 Dresses was one of the first movies to kick butt with a majority female team. With Aline Brosh McKenna as the writer, Anne Fletcher as the director, Katherine Heigl as the lead actress, and Priscilla Nedd-Friendly as the editor, nothing — not even the tight, ten-month deadline — would stop this powerhouse from achieving their goals.

Even critics who did not particularly love the film gave them props for finally involving women in more leadership roles,

according to Decider. Everyone clicked really well, and the ship sailed smoothly through the movie-making process.

17 The Most Infamous Scene Almost Got Cut


At first, the silly but touching karaoke scene with the song Bennie and the Jets almost didn't make it into the film. Aline and Anne went back and forth between ideas for the climactic song that would change everything — and for Alise, Bennie and the Jets just wasn't a fast enough song to dance to. Brown Sugar was the next best option for scene Alise said, in an article for Entertainment Weekly, but the two wanted the song to be something that everybody would know of without actually knowing all the words. Therefore, it was Bennie and the Jets that finally made the cut.

16 The Dress Dilemma

Us Weekly

The director of 27 Dresses, Anne Fletcher, told Reuters when picking out the dresses that Katherine would wear as a bridesmaid that she told her costume designer to get the biggest and ugliest things she could find.

Despite finding over 50 dresses and narrowing them down to 27, Anne Fletcher admitted that everything the leading lady would try on still looked beautiful on her. 

In order to make the dresses as over the top and as awful-looking as possible, Fletcher suggested more flowers, tulle, and a hat. The whole point was to make these dresses look as unflattering as possible on Heigl — and it’s safe to say that they did the job right.

15 There Was A Real Wedding Going On

Wedding Biography

Katherine Heigl — also known as Jane — told People that there was a little dental drama going on during the making of 27 Dresses. While this movie centers around brides, grooms, and bridesmaids, Katherine was planning her own real-life wedding during the shooting. Suddenly, she realized that she wasn't satisfied with her smile and opted to use Invisalign, which would sometimes get in the way of Katherine being able to say her lines properly. Furthermore, Malin Akerman (Tess Nichols) got married in real life during the making of the film, and several other members of the cast and crew felt that love was in the air.

14 She Really Didn’t Know The Lyrics


Back to the infamous Bennie and the Jets karaoke scene. When Katherine Heigl read over that part of the script, she scratched her head and wondered what the real lyrics were. After chatting about it with Anne Fletcher, she realized that the whole point of singing the lyrics wrong was to remain relatable in the storyline, as per Entertainment Weekly. Aline Brosh McKenna wrote the incorrect lyrics on purpose, noting that she was not married to the idea of them singing it right and would rather have them get it all wrong, as not many people know the words to the whole song. Even in imperfections, they nailed it.

13 The Process Took Six Years

Entertainment Weekly

Between writing, rejections, revising, shooting and editing, 27 Dresses took a whopping six years to complete. Aline recalls via Decider how frustrated she became with always having to make changes and new pitches. By June 2006 — when The Devil Wears Prada hit theatres — Aline said that she was close to calling it quits with her project, 27 Dresses. Ultimately, it was those who kept telling Aline to change the script until she got it right that encouraged her to keep fighting for her idea. Though about 60 percent of the original script got changed around, the end result was one that nobody could say no to.

12 There’s A Reason For That Cartoon Movie Poster Dress

Shepherd Frankel

Katherine Heigl was on fire as a television actress with a regular stint on Grey’s Anatomy, but producers feared that Heigl wouldn't cut it as a movie star. They figured that because not many people knew her as an actress on film, this would ruin the chances of a successful box office turn-out.

To combat any potential hesitance from the audience, an over-the-top poster was created with a cartoon looking dress that let moviegoers know that the same woman who worked on The Devil Wears Prada also worked on this film,

according to Decider. Needless to say, this iconic formula for trying to catch the crowd's eye worked wonders.

11 A Tight-Knit Cast


Scriptwriter Aline Brosh McKenna credited director Anne Fletcher for her humble and loving attitude on set. Reportedly, the cast and crew members referred to Anne as their mama, because she took all the time she could to help all the actors fulfill and nail the roles they were cast in, reveals Decider. Katherine Heigl, James Marsden, Malin Akerman, and Judy Greer all recall how fun it was to be on set — and how even afterward everybody still kept in touch and reflected fondly on the making of the iconic romance comedy. In many instances, actors don't always get along with everybody on set. 27 Dresses was one of the very few exceptions.

10 They Wanted To Make It A TV Show

Entertainment Weekly

Before the final decision came to make 27 Dresses into a film, this blockbuster rom-com was once considered for television instead. Aline Brosh McKenna revealed that even after ten years she still would like to see it be remade into a TV series, according to Decider.

A sequel was thought to be in the works not long after the movie’s release, but if anything, it seems like Aline is more keen on the idea of everyone tuning in weekly to see what kind of shenanigans Jane and Kevin will be up to next.

Regardless, Aline says she’s still over the moon happy with the success of the film.

9 What Men Were Expected To Take Away From The Film

Katherine Heigl

Although romantic comedies like 27 Dresses are generally aimed more towards the female audience, men can and often do enjoy these types of films. But in an article written by a critic in the New York Times, it states that men should probably steer clear of the film altogether. According to harsher critics, 27 Dresses is a movie that depicts men as unnecessary and dumb. Critics have even stated that men should be afraid after watching this movie — implying that all women desire a big and expensive wedding. Aline Brosh McKenna says that’s not the case, however, and that men enjoy the film for its high-quality acting and witty script.

8 The Part Was Given To James Marsden As A Joke

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James Marsden — who was working on Hairspray at the time — recalls how director Anne Fletcher showed up on the Hairspray set one day and tried to recruit James Marsden as a joke, as per Entertainment Weekly. Anne stated that Katherine Heigl would be playing the lead and that he should play the love interest.

Of course, James laughed it off and never thought he’d hear back from her again.

After a week of thinking it over, Anne returned to the set and said that although she had meant it as a joke at first; she ultimately thought he would be the best choice for the role of Kevin.

7 Never A Bad Day On Set

via Just Jared

In any work environment, there are good days and bad days. During the making of 27 Dresses, however, bad days didn't exist. During the last day of filming, Anne Fletcher paints the picture of a happy cast and crew that became a like family throughout the whole process, according to Decider.

Not a single actor or crew member was in a bad mood, and by the end of it all, they celebrated their last day in typical 27 Dresses fashion with a karaoke session and cheers all around.

Everyone was sad to see everything come to a close and move on to different projects, but still, they remained grateful to have been a part of such an amazing experience.

6 The Dance Scenes Were Intimidating For The Actors

Katherine Heigl

Whenever there is music, there will always be dancing. Most of the actors were not professional level dancers; so, their choreographer helped them get over their fear of dancing on camera. Everyone knew what their limits were, Fletcher said, and everyone knew where they were supposed to go and what they were supposed to do. But for actors like Katherine Heigl and James Marsden, they admitted that they were terrified at first to be this vulnerable.

Realistically, since their characters wouldn't be great dancers in real life— they were told not to focus on perfection and just have fun,

as per Entertainment Weekly. This made it a lot easier for the actors to perform their smooth moves.

5 The Last Prominent Rom-Com

Finding Wonderland

27 Dresses went on to slide into the number two spot at the box office, and it has proven itself to be one of the greatest rom-coms in the history of film. Entertainment Weekly notes that since the movie’s release ten years ago, romantic comedies have taken a different turn. Either appearing on streaming networks, television or going in an edgier direction, it’s said that 27 Dresses was one of the last prominent, mid-budget romantic comedies to come from Hollywood studios. However, should their dreams of a sequel come to pass, it may not be long before a good rom-com finds itself back on the big screen.

4 Katherine Heigl Actually Liked One Of The Dresses

Los Angeles Times

There was one dress in particular that Katherine Heigl said she would wear again. Amongst all of the not-so-flattering choices her character kept hidden in her closet, Katherine said that her most favorite of all was the short, yellow dress, saying that it was the most flattering and yet still very outrageous and absurd, as revealed by InStyle Magazine. The rest of the bridesmaid dresses were meant to look awkward and uncomfortable for the sake of conveying Jane’s slight frustration with never finding a groom of her own. From scuba themes to Elvis Presley style gowns, fans were happy to see Jane finally have her dream wedding in the end.

3 Heigl Didn’t Want A Big Wedding Because Of The Movie

Just Jared

When Katherine Heigl was asked about her real-life wedding — whether it was going to be just as fabulous and extravagant as the one in the movie — Heigl proudly stated that she had felt like she already had the big wedding of every girl’s dream in the movie. Thus, a much simpler wedding planned at Christmastime would be just as wonderful for her and her real-life soon to be husband at the time, according to Access Online. With 27 Dresses — a movie that portrays a woman who desperately dreams of a fantastic wedding— Heigl said that because of the movie’s focus on extravagant ceremonies, she'd rather focus on what weddings are all about in the first place.

2 Katherine Heigl Almost Didn’t Get Cast


Because Katherine Heigl was seen as mostly a TV drama actress rather than someone who could handle a full on film — producers were hesitant when Anne Fletcher brought her on board. It didn't take long though for everyone to realize that they had made the best choice.

As Fletcher recalls, as soon as Heigl started reading the script, she knew she was the right person for the part,

as disclosed by Decider. Anne mentioned how it was as if Katherine literally became Jane— that she was very impressed. Now, fans of 27 Dresses see Heigl as the woman who played Jane in their favorite rom-com — and thus the film became a high point in her career.

1 The Most Impossible Scene

via just jared

When asked how she managed to go back and forth between two weddings in one night and make changes to her wardrobe in the back of a taxi, Heigl answered that this scene was considered by her to be the most hilarious and impossible. She noted that there was no possible way that her character Jane could have gone to and fro so quickly to dance to two electric slides, as per InStyle Magazine. She also said that the scene was one of her favorites — due in part to it being fun and a great way to show audiences out there just exactly the kind of woman Jane is.

References: Decider, Reuters, Closer Weekly, Entertainment Weekly, InStyle, Us Magazine, New York Times Access Online

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