If you found yourself wooed by the romantic charm of “Pretty Woman” (1990), there’s a treasure trove of movies waiting for your viewing pleasure. From modern-day Cinderella tales to stories of unexpected love blossoming against all odds, these movies capture the essence of romance, wit, and allure reminiscent of Julia Roberts and Richard Gere’s iconic pairing.

Whether you’re in the mood for heartwarming love stories or tales of self-discovery, these 10 films promise to whisk you away on knee-shaking romantic journeys. From the glittering streets of New York City to the sun-soaked landscapes of Europe, these films offer a range of settings and narratives to satisfy your craving for romance and escapism.

So grab your popcorn, settle into your favorite spot on the couch, and let these movie titles take you to worlds where love conquers all and happily ever afters are always within reach.

1. Breakfast at Tiffany’s (1961)

Movies like Pretty Woman - Breakfast at Tiffany's

Audrey Hepburn’s iconic role as the charming New Yorker Holly Golightly makes “Breakfast at Tiffany’s” one of the most sought-after romantic comedies. Holly, a young socialite with a mysterious past, captures the attention of Paul, a struggling writer, and her neighbor.

The film revolves around their relationship as Paul becomes acquainted with Holly’s past and her desire to live a carefree, sophisticated life. Hepburn’s performance as Holly is undeniably impressive as she brings out the character’s charm, elegance, and vulnerability.

Just as Audrey Hepburn’s “Breakfast at Tiffany’s” is famous and still celebrated for its stylish cinematography capturing the essence of a big city in the early ’60s, Julia Roberts’ “Pretty Woman” is also famous for capturing the exact mood of Los Angeles.

The iconic opening scenes of both films capture our attention to the quirky side of our protagonists, for instance, Holly standing in front of Tiffany & Co. and Vivian getting ready in her glamorous apartment in LA. Similar to “Pretty Woman,” which used some timeless rock and roll music, “Breakfast at Tiffany’s” music is also unforgettable, especially the classic song “Moon River,” which won an Academy Award for Best Original Song.

“Breakfast at Tiffany’s” is a must-watch for those interested in classic cinema and the evolution of romantic comedies, as it introduced elements of complex characters while exploring love, identity and the pursuit of happiness. Much like Vivian’s character in ‘Pretty Woman,’ Holly’s character too challenges societal expectations in her journey of self-discovery, making the film a timeless piece of filmography.

2. Cocktail (1988)

Movies like Pretty Woman - Cocktail (1988)

Similar to Vivian in “Pretty Woman,” who comes to a different city with big dreams, Tom Cruise portrays Brian Flanagan, a young bartender who moves to New York City with dreams of making it big in “Cocktail.”

The film follows Brian through his ups and downs in his personal and professional life, including his tumultuous relationship with Jordan Mooney and his friendship with Doug Coughlin. “Cocktail” was one of those movies that introduced a more adventurous and glamorous element to the typical romantic storyline while also exploring ambition, friendship, love, and the pursuit of the American Dream.

Just as Richard Gere’s relationship with his longtime lawyer partner, Philip Stuckey, is tested in the film, the dynamic between Brian and Doug highlights the complexities of friendship, loyalty, and competition in “Cocktail.”

One iconic aspect of the film is its portrayal of flair bartending culture, which popularized the flashy, acrobatic style of bartending. Tom Cruise’s character performs a memorable bartending routine to the song “Hippy Hippy Shake,” significantly influencing subsequent films and TV shows featuring bartending sequences.

3. My Best Friend’s Wedding (1997)

Movies like Pretty Woman - My Best Friend's Wedding

Both “Pretty Woman” and “My Best Friend’s Wedding” feature Julia Roberts in leading roles, exploring themes of love and self-discovery. P.J. Hogan’s 1997 rom-com film revolves around Julianne, who realizes she’s in love with her best friend Michael just as he announces his engagement to Kimberly. Determined to win him back, Julianne uses her quirky tactics and sometimes even schemes to sabotage the wedding.

We see Roberts’ character evolving as she forces herself to confront her own feelings, just as she did in “Pretty Woman.” The similarity of both characters leads to her acknowledging what she truly wants and needs.

“My Best Friend’s Wedding” is still famous for the memorable musical scene featuring the cast singing along to “I Say a Little Prayer,” which went on to become emblematic of the film’s chemistry between the characters.

Talking about movies like Pretty Woman, “My Best Friend’s Wedding” explores the idea of letting go and finding happiness in unexpected places, with strong, independent female protagonists driving the narrative.

4. Notting Hill (1999)

Movies like Pretty Woman - Nottign Hill.jpg

Roger Michell’s “Notting Hill” stars Julia Roberts as Anna Scott, a famous Hollywood actress, and Hugh Grant as William “Will” Thacker, a bookstore owner in the Notting Hill district of London. The film follows the unlikely romance between Anna and Will after they meet by chance in his bookstore.

The all-time classic romantic film explores the idea of love transcending social barriers, the impact of fame on personal relationships, and the importance of authenticity and acceptance in romantic connections. The 1999 film is very close to “Pretty Woman” for this reason and also touches on the concept of fate and the idea that love can be found in unexpected places.

“Notting Hill” is still considered to be one of those films that brought a refreshing take on the characters’ vulnerability to the typical Hollywood romance. One iconic aspect of “Notting Hill” is the scene where Anna and Will share a private moment in a park surrounded by bluebells. This intimate and romantic setting became emblematic of the film’s fairy-tale-like portrayal of love and romance.

The film garnered appreciation for both Roberts and Grant’s performances, depicting the unlikely romance between a seemingly ordinary person and someone from a higher social status, which is quite similar to that shown in movies like “Pretty Woman.”

5. Runaway Bride (1999)

Movies like Pretty Woman - Runaway Bride (1999)

Since we are talking about movies like Pretty Woman, one cannot go without mentioning Gary Marshall’s famous rom-com – “Runaway Bride.” The film again stars Julia Roberts in the leading role as Maggie Carpenter, along with Richard Gere as Ike Graham.

The story revolves around Maggie, who has developed a reputation for leaving men at the altar, and Ike, a cynical journalist who sets out to write a story about her. As Ike spends time with Maggie, he begins to uncover the reasons behind her behavior and discovers his own feelings for her.

The film explores commitment-phobic characters who fear the whole idea of intimacy and relationships, which is very close to Richard Gere playing his character in “Pretty Woman.” “Runaway Bride” challenges the stereotypes about women and marriage, presenting Maggie as a complex and multidimensional character with agency and autonomy.

Similar to “Pretty Woman,” the film emphasizes the importance of authenticity and communication in romantic relationships, moving away from formulaic rom-com tropes towards a more nuanced exploration of love and commitment.

6. Two Weeks Notice (2002)

Movies like Pretty Woman - Two Weeks Notice

“Two Weeks Notice” follows Lucy (Sandra Bullock), a dedicated environmental lawyer, who becomes the chief counsel for George (Hugh Grant), a charming but irresponsible real estate tycoon. As Lucy juggles her demanding job and her growing feelings for George, she struggles to maintain her principles and balance her personal and professional life.

The all-time classic romance film explores the conflict between career aspirations and personal relationships of the characters along with the importance of integrity and standing up for one’s beliefs, and the transformative power of love. The film also touches on the dynamics of power and control within romantic relationships that are very similar to the dynamics of Vivian and Edward in “Pretty Woman.”

“Two Weeks Notice” continued the trend of featuring strong, independent female protagonists who challenge traditional gender roles and expectations. Much like “Pretty Woman,” where we witness Vivian’s character as an unabashed young, intelligent woman, Lucy in “Two Weeks Notice” is a smart woman who is unafraid to speak her mind and pursue her goals.

Additionally, the film is also identical to “Pretty Woman’s” narrative (where Vivian shares that she used to imagine for a prince charming to rescue her) emphasizes the importance of mutual respect and equality in romantic relationships maintaining one’s integrity and staying true to oneself in the pursuit of love and happiness.

7. Maid in Manhattan (2002)

“Maid in Manhattan” revolves around Marisa Ventura (Jennifer Lopez), a single mother working as a maid in a luxury hotel in Manhattan. Through a case of mistaken identity, Marisa is mistaken for a wealthy guest by Chris Marshall (Ralph Fiennes), a politician running for the United States Senate. As their romance blossoms, Marisa struggles to maintain the facade of her true identity.

As far as movies like “Pretty Woman” are concerned, the film explores the idea of social class and the barriers it creates in relationships. Similar to Vivian from “Pretty Woman,” where she works as a prostitute struggling to make ends meet, Marisa too comes from a working-class background, facing prejudice and judgment from those in higher social circles.

Again, holding similarities with “Pretty Woman,” “Maid in Manhattan” brought some changes to the romantic comedy genre at the time by incorporating elements of the classic Cinderella story into a modern setting. One iconic instance from the film is the scene where Marisa tries on expensive clothing and jewelry, reminiscent of Cinderella trying on the glass slipper.

The film shares similarities with Pretty Woman where the female lead is introduced to a world of luxury and glamour, challenging societal expectations and norms. However, “Maid in Manhattan” distinguishes itself by setting the story in a contemporary urban environment and focusing more on issues of identity and authenticity.

8. How to Lose a Guy in 10 Days (2003)

Kate Hudson and Matthew McConaughey’s instant hit and an all-time favorite romantic film “How to Lose a Guy in 10 Days,” follows Andie, a writer for a women’s magazine assigned to write an article on how to lose a guy in 10 days by exhibiting all the classic behaviors that drive men away.

At the same time, Benjamin, an advertising executive, makes a bet with his colleagues that he can make any woman fall in love with him in 10 days. Their paths cross, leading to a series of comedic misunderstandings and romantic entanglements.

The film explores the dynamics of modern dating and relationships while also examining the games people play in the early stages of courtship and the challenges of balancing personal goals with romantic pursuits.

It also delves into the importance of honesty and communication in building meaningful connections. The classic battle of the sexes trope combined with humor, romance, and satire made the film entertaining and relatable to generations to date.

As far as movies like “Pretty Woman” (1990) are concerned, “How to Lose a Guy in 10 Days” features a storyline where two individuals from different backgrounds and with conflicting motives find themselves drawn to each other. Both films explore themes of love, trust, and personal growth within the context of unconventional romantic relationships.

9. The Holiday (2006)

The Holiday

Nancy Meyers’ “The Holiday” stars Cameron Diaz, Kate Winslet, Jude Law, and Jack Black. The film revolves around two women, Iris (Kate Winslet) and Amanda (Cameron Diaz), who swap homes for the holidays to escape their respective romantic troubles.

While staying in each other’s homes, they each meet and fall in love with new men: Iris with a charming British man named Miles (Jack Black), and Amanda with Iris’s brother Graham (Jude Law).

The film is highly recommended for those who intend to watch a rom-com in order to heal heartbreak and still have hope for the unexpected nature of love. In “The Holiday,” our protagonists undergo personal growth and find solace in their new surroundings, ultimately learning to embrace themselves and what they truly desire in life.

The film grabs your attention quickly, especially when we are introduced to Iris’ charming English cottage, boosting a cozy and picturesque setting that becomes emblematic of the film’s romantic and feel-good atmosphere, providing a beautiful backdrop for the unfolding love stories.

Much like “Pretty Woman,” “The Holiday” features a romantic storyline involving a wealthy, charming man and a woman who initially feels out of her depth in their social circle.

Both films explore themes of love, self-discovery, and the transformative power of romantic relationships. Additionally, they share a similar blend of humor and romance, with memorable characters and witty dialogue driving the narrative forward.

10. The Proposal (2009)

Sandra Bullock and Ryan Reynolds star in “The Proposal,” which also deserves mention when discussing romantic movies like “Pretty Woman.” The film centers on Margaret, a Canadian book editor facing deportation from the United States due to an expired visa. In a desperate attempt to stay in the country, she convinces her assistant, Andrew, to marry her under the guise of a fake engagement.

The movie captures the good-natured banter between Margaret and Andrew, creating a humorous relationship that is a result of Sandra and Ryan’s strong performances and on-screen chemistry, reminiscent of Vivian and Edward’s relationship in “Pretty Woman.”

Sandra’s character shares similarities with Edward, initially portraying toughness and demanding behavior, but as the story progresses, her vulnerabilities and complexities are revealed, mirroring Edward’s character development as she grows close to Andrew while navigating their transactional relationship.

Examining the similarities between Vivian and Margaret’s characters, one can observe that both are strong, independent women challenging traditional gender roles often seen in the genre.

Similar to “Pretty Woman,” “The Proposal” blends humor and emotional depth, exploring the protagonist’s perspective individually and in a companion relationship, going beyond the superficial aspects of a character.

Read More: 15 Movies to Watch if You Like Midnight in Paris (2011)

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