Top 10 Romantic Comedies Similar to 27 Dresses

There are many popular romantic comedies, such as the 2008 film "27 Dresses" starring Katherine Heigl and James Marsden. Directed by Anne Fletcher, the movie follows Jane (Heigl), who has been a bridesmaid 27 times but never a bride. When her younger sister Tess (Malin Åkerman) gets engaged to the man Jane secretly loves (who also happens to be her boss), Jane struggles emotionally as she helps with wedding planning and maid of honor duties. Along the way, she navigates romantic tension with Kevin (Marsden), a cynical writer of wedding announcements.

"27 Dresses" was a hit when it came out in 2008 and is still considered one of the best movies for Katherine Heigl and James Marsden. Heigl had previously found success with the raunchy romantic comedy "Knocked Up" in 2007 and her role as Dr. Izzie Stevens in "Grey's Anatomy." Although this film was one of the few rom-coms to feature Marsden as the leading man, Heigl has starred in several other romantic comedies from the 2000s and 2010s, many of which also revolve around weddings.

27 Dresses is available to stream on Netflix and Disney+.

The Ugly Truth (2009)

Rent On Amazon Prime Video & Apple TV

Gerard Butler and Katherine Heigl in The Ugly Truth - Rent On Amazon Prime Video & Apple TV - The Ugly Truth (2009)

In 2010, Heigl starred in "Life As We Know It".

Stream On Max

Katherine Heigl and Josh-Duhamel in Life As We Know It - Stream On Max - Life As We Know It (2010)

In 2013, Heigl starred in The Big Wedding, which follows the chaotic events leading up to a family wedding. Despite being divorced for years, Don (Robert De Niro) and Ellie (Diane Keaton) pretend to still be married for the sake of their adopted son's biological mother, who is very Catholic and disapproves of divorce. As the wedding approaches, secrets are revealed, relationships are tested, and hilarity ensues. The film explores themes of love, family, and the complexities of relationships in a light-hearted and comedic way.

Stream On Max

Robert DeNiro, Diane Keaton, and Katherine Heigl in The Big Wedding (2013) - Stream On Max

In 2015, Heigl starred in a film called Jenny's Wedding.

Stream On AMC+

Alexis Bledel and Katherine Heigl in Jenny's Wedding - Stream On AMC+ - Jenny's Wedding (2015)

My Best Friend's Wedding (1997)

In "Jenny's Wedding," Heigl finally gets to play the bride herself after portraying the sister of the bride and groom. Jenny, the titular character, is openly gay but keeps her relationship with her girlfriend, Kitty, a secret from her conservative family. When Jenny finally comes out to her family and announces her engagement to Kitty, they are shocked. Similar to Tess in "27 Dresses," Jenny hides her true self, but her situation is more relatable and sympathetic.

Stream On Netflix

Jules (Julia Roberts) stares at Michael (Dermot Mulroney) in My Best Friend's Wedding. - Stream On Netflix - My Best Friend's Wedding (1997)

This beloved rom-com from the Golden Age may be one of the oldest films on this list, but My Best Friend's Wedding from 1997 still shares similarities with 27 Dresses. Julia Roberts, the queen of rom-coms, stars as Julianne, who made a pact with her lifelong friend Michael (played by Dermot Mulroney) that they would marry if they were both single at 28. However, when Michael reveals he is engaged to 20-year-old Kimmy (played by Cameron Diaz), Jules realizes she has feelings for him. She agrees to be Kimmy's maid of honor while secretly plotting to ruin the wedding and split the couple up.

Similar to 27 Dresses, the main character in My Best Friend's Wedding also agrees to be the maid of honor at a wedding despite being in love with the groom. One of the most iconic and memorable scenes in My Best Friend's Wedding involves a hilarious singalong moment in a bar. However, Kimmy's karaoke performance is much more cringeworthy and awkward compared to Jane and Kevin's drunken "Bennie and the Jets" duet in 27 Dresses.

Runaway Bride (1999)

Stream On Paramount+

Jules (Julia Roberts) wears a cowboy hat while Ike (Richard Gere) wears a baseball cap in Runaway Bride. - Stream On Paramount+ - Runaway Bride (1999)

Runaway Bride, a romantic comedy starring Julia Roberts from the '90s, shares similarities with the movie 27 Dresses from 2008. In this film, Julia Roberts plays the role of a bride-to-be who keeps getting cold feet. Just like many other rom-coms, Runaway Bride revolves around the theme of weddings. What makes it even more alike to 27 Dresses is that both movies feature a journalist as the male lead, who ends up writing a story about the female lead's unique wedding trend.

In the movie "The Wedding Planner" (2001), we meet Maggie (Roberts) who is known for being a serial bride. On the other hand, Jane is a serial bridesmaid, always there to support her friends on their big day. Ike (Gere) kicks off the story by writing a not-so-flattering article about Maggie in the beginning of "Runaway Bride", while Kevin's piece about Jane is featured later in the third act of "27 Dresses". Despite the differences in their stories, both Ike and Kevin are drawn to the fact that their subjects have been involved in numerous weddings. Maggie has left three fiancés at the altar, earning her the title of "the runaway bride", while Jane has stood by as a bridesmaid a whopping 27 times, leading to her being known as a "perennial bridesmaid".

Stream On Hulu

Matthew McConaughey And Jennifer Lopez in The Wedding Planner - Stream On Hulu - The Wedding Planner (2001)

The Wedding Planner, like 27 Dresses, is a romantic comedy that revolves around the process of planning a wedding. In this film, Jennifer Lopez portrays Mary, a wedding planner in San Francisco, who finds herself developing feelings for the groom, Steve (Matthew McConaughey), of the lavish wedding she is organizing. Similarly to 27 Dresses, Judy Greer plays the role of Mary's best friend and colleague, who also harbors romantic feelings for the groom. Another familiar face in The Wedding Planner is Justin Chambers, known for his role as Dr. Alex Karev on Grey's Anatomy from 2005 to 2020, further connecting the two films through Katherine Heigl, the star of 27 Dresses.

Made Of Honor (2008)

Stream On Peacock & fuboTV

Patrick Dempsey and Michelle Monaghan in Made of Honor - Stream On Peacock & fuboTV - Made Of Honor (2008)

Made of Honor, released in the same year as 27 Dresses, tells the story of Tom (played by Patrick Dempsey), a guy who has a reputation for dating many women and not settling down. However, he suddenly realizes that he is in love with his best friend, Hannah (played by Michelle Monaghan), right when she announces her engagement. In a plot similar to My Best Friend's Wedding, Tom decides to become Hannah's "maid" of honor in order to stop the wedding and win her over. Like 27 Dresses, the movie also features a main character who is part of a wedding party while secretly harboring feelings for one of the people getting married.

Bride Wars (2009)

Made of Honor also includes several Grey's Anatomy actors, with its male lead being a former main cast member of the medical drama alongside Heigl. Dempsey portrayed Dr. Derek "McDreamy" Shepherd on Grey's Anatomy from 2005 to 2015. Kevin McKidd, who portrays Colin, Hannah's fiancé in Made of Honor, is another Grey's Anatomy star, continuing to play Dr. Owen Hunt on the show since joining the cast in the same year that Made of Honor was released.

Stream On fuboTV

Liv (Kate Hudson) and Emma (Anne Hathaway) sit and stare at each other in their wedding dresses in Bride Wars. - Stream On fuboTV - Bride Wars (2009)

The Proposal is a romantic comedy released in 2009 starring Sandra Bullock and Ryan Reynolds. The story follows Margaret, a high-powered book editor, who is faced with deportation back to Canada. In order to stay in the United States, she convinces her assistant, Andrew, to marry her. The two must navigate a fake engagement and meet each other's families, leading to unexpected feelings and realizations. As Margaret and Andrew spend more time together, they begin to see each other in a new light and question their initial assumptions about each other.

Stream On Hulu & Apple TV

Margaret (Sandra Bullock) and Andrew (Ryan Reynolds) stand together in her office in The Proposal. - Stream On Hulu & Apple TV - The Proposal (2009)

The Proposal, another romantic comedy released the year after 27 Dresses, tells the story of Margaret (Sandra Bullock), the editor-in-chief at a book publishing house who is facing deportation to Canada. To avoid this, she strikes a deal with her assistant Andrew (Ryan Reynolds) to fake an engagement. However, their plan takes an unexpected turn when they visit Andrew's family in Alaska. Directed by Anne Fletcher, who also directed 27 Dresses, The Proposal also stars Malin Åkerman, known for her role as Jane's sister Tess in the 2008 rom-com.

Editor's P/S:

This article provides a comprehensive overview of several romantic comedies that share similarities with the beloved film "27 Dresses." It highlights the themes of weddings,