10 Best Movies Like 27 Dresses | Similar-List

“27 Dresses” tells the story of Jane (Katherine Heigl), a perpetual bridesmaid who has walked down the aisle 27 times but has never been the bride. The narrative takes a twist when Jane’s younger sister, Tess (Malin Åkerman), gets engaged to the man Jane secretly loves. As Jane grapples with her emotions, she encounters Kevin (James Marsden), a wedding announcement writer who adds a dose of cynicism and romance to her life. Released in 2008, “27 Dresses” quickly became a beloved romantic comedy, thanks to its charming storyline and engaging performances. The film's blend of humor, heart, and relatable themes about love and self-discovery resonated with audiences worldwide.

“27 Dresses” holds a special place in the romantic comedy genre due to its endearing plot and memorable characters. Katherine Heigl was already gaining significant attention for her roles in the 2007 hit “Knocked Up” and as Dr. Izzie Stevens on “Grey’s Anatomy.” This film highlighted her versatility and solidified her status as a rom-com favorite. James Marsden’s portrayal of Kevin also added a delightful dynamic to the movie. Heigl’s career during this period included several successful romantic comedies, many of which centered around weddings, establishing her as a staple in the genre. Films like “The Ugly Truth” and “Life As We Know It” further showcased her ability to captivate audiences with charm and comedic timing.

For fans eager to learn more about Katherine Heigl’s career and her impact on the romantic comedy genre, there are several related articles to explore. For instance, “What Happened to Katherine Heigl” provides insights into her career trajectory and recent work. Additionally, pieces like “Katherine Heigl’s Best Rom-Com Roles” and “The Evolution of Katherine Heigl: From TV Star to Film Icon” offer a deeper look into Heigl’s filmography and contributions to the genre. If you enjoyed “27 Dresses,” here are some other romantic comedies with similar themes, tones, and character dynamics:

10 Best Movies Like 27 Dresses

Knocked Up (2007)

• Director: Judd Apatow
• Release Date: December 21, 2012
• Cast: Paul Rudd, Leslie Mann, Maude Apatow
• Runtime: 134 minutes

“Knocked Up” follows the unexpected journey of Alison Scott (Katherine Heigl), an ambitious career woman whose one-night stand with the slacker Ben Stone (Seth Rogen) results in an unplanned pregnancy. The film humorously explores their evolving relationship as they navigate the challenges of impending parenthood. Released in 2007, “Knocked Up” was a critical and commercial success, blending raunchy humor with heartfelt moments and marking a standout moment in the careers of both Heigl and Rogen.

“Knocked Up” stands out in the comedy genre for its fresh take on the romantic comedy formula. It was a significant film for Katherine Heigl, who, having achieved prominence with “Grey’s Anatomy,” showcased her comedic talents in this role. Seth Rogen, already known for his work on “Freaks and Geeks” and “The 40-Year-Old Virgin,” further cemented his status as a leading comedic actor. Directed by Judd Apatow, the film is noted for its blend of humor and genuine emotion, setting a new standard for comedy in the late 2000s. Apatow’s knack for combining humor with real-life situations contributed to the film’s unique appeal.

“Knocked Up” shares thematic similarities with “27 Dresses” in exploring romantic relationships and personal growth. While “27 Dresses” delves into the complexities of a woman’s role in multiple weddings and her romantic aspirations, “Knocked Up” focuses on the consequences of an unexpected pregnancy on a developing relationship. Both films blend comedy with emotional depth, showcasing characters who must confront their challenges and adapt to new realities. Katherine Heigl’s performance in “Knocked Up” further underscores her versatility as she navigates her role's comedic and dramatic aspects, making it a complementary film for those who enjoyed the heartfelt and humorous elements of “27 Dresses.”

The Ugly Truth (2009)

• Director: Robert Luketic
• Release Date: July 24, 2009
• Cast: Katherine Heigl, Gerard Butler, Bree Turner, Eric Winter
• Runtime: 96 minutes

In “The Ugly Truth,” Katherine Heigl stars as Abby Richter, a television producer trying to advance her career while managing her personal life. Her world is turned upside down when Mike Chadway (Gerard Butler), a brash and chauvinistic morning show host, joins her team. The film explores their contentious relationship as they clash over their views on love and relationships, but soon discover an unexpected connection.

Like “27 Dresses,” “The Ugly Truth” features Katherine Heigl in a leading romantic role where she must navigate a challenging relationship. The film similarly contrasts a romantic female lead with a cynical male counterpart, creating a dynamic filled with humor and tension. The chemistry between Heigl and Butler drives the narrative, making the romantic journey engaging and entertaining. The film’s comedic take on the battle of the sexes echoes the playful yet insightful tone found in “27 Dresses,” adding depth to its humor through genuine emotional moments.

Life As We Know It (2010)

• Director: Greg Berlanti
• Release Date: October 2, 2010
• Cast: Katherine Heigl, Josh Duhamel, Josh Lucas
• Runtime: 112 minutes

“Life As We Know It” stars Katherine Heigl and Josh Duhamel as Holly and Eric, two godparents who are forced to raise their late friends’ child together after a tragic accident. Initially, Holly and Eric have a strained relationship, marked by animosity and conflicting parenting styles. As they navigate the challenges of co-parenting, their relationship evolves from friction to deep connection and mutual respect.

Like “27 Dresses,” “Life As We Know It” delves into the dynamics between two characters who must navigate an unconventional situation together. While “27 Dresses” explores the complexities of romantic relationships and family dynamics through the lens of weddings, “Life As We Know It” presents a more dramatic take on relationships through parenting challenges. Both films highlight how personal growth and unexpected connections can lead to profound emotional journeys. The chemistry between Heigl and Duhamel adds depth to their characters’ evolving relationship, offering a mix of humor and heartfelt moments akin to those in “27 Dresses.”

The Big Wedding (2013)

• Director: Justin Zackham
• Release Date: April 26, 2013
• Cast: Robert De Niro, Diane Keaton, Katherine Heigl, Robin Williams
• Runtime: 89 minutes

In “The Big Wedding,” a divorced couple, Don (Robert De Niro) and Ellie (Diane Keaton) are thrust back together when they must pretend to be married during their adopted son’s wedding weekend. The catch is that their son’s biological mother is a devout Catholic who insists that the couple maintain the facade. The film is a comedic exploration of family dynamics, secrets, and the chaos that ensues when old wounds are reopened.

Much like “27 Dresses,” “The Big Wedding” features a wedding setting as the backdrop for exploring intricate family dynamics. The film delves into themes of family cohesion and the complexities of personal relationships, similar to how “27 Dresses” navigates the emotional landscapes of its characters. The ensemble cast, including Katherine Heigl, brings an additional layer of humor and heartfelt moments, mirroring the blend of comedy and romance found in “27 Dresses.”

Jenny’s Wedding (2015)

• Director: Mary Agnes Donoghue
• Release Date: July 31, 2015
• Cast: Katherine Heigl, Alexis Bledel, Tom Wilkinson
• Runtime: 94 minutes

“Jenny’s Wedding” stars Katherine Heigl as Jenny, a woman who decides to come out to her conservative family and announce her engagement to her girlfriend, Kitty (Alexis Bledel). The film poignantly explores family acceptance, personal identity, and courage to be true to oneself. Jenny's journey is navigating familial expectations while striving to live authentically.

“Jenny’s Wedding” shares thematic elements with “27 Dresses” by focusing on personal revelations and the complexities of familial relationships. Both films center on the protagonist’s struggle with personal desires versus family expectations, though “Jenny’s Wedding” delves deeper into the challenges of coming out and achieving acceptance. The emotional depth and exploration of identity in “Jenny’s Wedding” complement the heartfelt and humorous approach of “27 Dresses,” making it a meaningful watch for fans of character-driven stories.

My Best Friend’s Wedding (1997)

• Director: P.J. Hogan
• Release Date: June 20, 1997
• Cast: Julia Roberts, Dermot Mulroney, Cameron Diaz, Rupert Everett
• Runtime: 105 minutes

In “My Best Friend’s Wedding,” Julia Roberts stars as Julianne Potter, who realizes she is in love with her best friend, Michael (Dermot Mulroney), just as he becomes engaged to another woman, Kim (Cameron Diaz). Determined to win him back, Julianne concocts a series of schemes to sabotage the wedding while grappling with her feelings and the consequences of her actions.

“My Best Friend’s Wedding” and “27 Dresses” both center on themes of unrequited love and the chaos that ensues when a wedding tests a protagonist’s romantic feelings. The comedic yet poignant exploration of love and friendship in “My Best Friend’s Wedding” aligns with the emotional and humorous tones of “27 Dresses.” Both films highlight the complexities of relationships and the lengths one will go to in the name of love, offering a blend of heartfelt drama and comedy.

Runaway Bride (1999)

• Director: Garry Marshall
• Release Date: July 30, 1999
• Cast: Julia Roberts, Richard Gere, Joan Cusack, Hector Elizondo
• Runtime: 116 minutes

“Runaway Bride” stars Julia Roberts as Maggie Carpenter, a woman notorious for leaving her fiancés at the altar. When journalist Ike Graham (Richard Gere) starts covering her story, he becomes intrigued by Maggie’s elusive nature. As he digs deeper, he uncovers the reasons behind her flight from commitment and finds himself drawn into her life.

“Runaway Bride” and “27 Dresses” explore the dynamics of weddings and the personal issues surrounding commitment. While “Runaway Bride” delves into the reasons behind Maggie’s reluctance to marry, “27 Dresses” focuses on the personal journey of a perennial bridesmaid. The films both use the wedding setting to unravel deeper emotional stories, with a blend of romance and comedy that highlights the challenges of love and commitment.

The Wedding Planner (2001)

• Director: Adam Shankman
• Release Date: January 26, 2001
• Cast: Jennifer Lopez, Matthew McConaughey, Bridgette Wilson, Justin Chambers
• Runtime: 103 minutes

In “The Wedding Planner,” Jennifer Lopez plays Mary Fiore, a successful wedding planner who falls for a charming doctor, Steve Edison (Matthew McConaughey), only to discover that he is the fiancé of one of her clients. The film blends romantic comedy with the trials of working in the wedding industry as Mary navigates her conflicting feelings and professional ethics.

“The Wedding Planner” and “27 Dresses” utilize the wedding setting to explore romantic entanglements and professional challenges. The comedic elements in “The Wedding Planner,” combined with the dilemmas Mary faces as she balances her career and personal life, resonate with the light-hearted yet emotionally charged narrative of “27 Dresses.” Both films look charmingly at the intersection of love and work within the wedding industry.

Made of Honor (2008)

• Director: Paul Weiland
• Release Date: May 2, 2008
• Cast: Patrick Dempsey, Michelle Monaghan, Sydney Pollack
• Runtime: 101 minutes

“Made of Honor” stars Patrick Dempsey as Tom, a charming womanizer who realizes he is in love with his best friend, Hannah (Michelle Monaghan), just as she gets engaged to another man. Tom takes on the role of Hannah’s maid of honor to win her back, leading to humorous and heartfelt moments as he navigates the role's challenges and his feelings.

“Made of Honor” shares similarities with “27 Dresses” in exploring romantic feelings that emerge in the context of a wedding. Both films feature protagonists dealing with complicated emotions and relationships amidst wedding preparations. The mix of comedy and romance in “Made of Honor” complements Jane's charming yet tumultuous journey in “27 Dresses,” offering a similar blend of humor and heartfelt moments.

Bride Wars (2009)

• Director: Gary Winick
• Release Date: January 9, 2009
• Cast: Kate Hudson, Anne Hathaway, Kristen Johnston
• Runtime: 90 minutes

In “Bride Wars,” Kate Hudson and Anne Hathaway star as Liv and Emma, two best friends who become adversaries when their weddings are scheduled on the same day at the same venue. The film showcases their increasingly outrageous antics as they try to outdo each other, leading to a humorous examination of friendship and rivalry.

“Bride Wars” and “27 Dresses” both use the wedding setting to explore female friendships and the complexities of romantic relationships. While “27 Dresses” focuses on one woman’s journey through multiple weddings, “Bride Wars” highlights the competitive nature that can arise between friends when weddings are involved. The comedic exploration of friendship and rivalry in “Bride Wars” resonates with the humorous and emotional undertones found in “27 Dresses,” making it a fitting recommendation for fans of the genre.

“27 Dresses” continues to charm audiences with its delightful mix of romance and comedy. The recommended movies offer similar experiences, blending romantic tension, engaging storylines, and memorable characters. If you loved “27 Dresses,” these films will provide an equally enjoyable viewing experience.