Our Picks for the Best Romantic Comedies of All Time

No matter what the 2020s are offering to us in terms of technology and pop culture, one thing is definitely missing. And that is romantic comedies! Whether you like or hate them, rom-coms have been a staple in the movie industry in the 90s and Y2K era.

However, lately, they seem to have disappeared into thin air. So, what is the next best thing to do? Rewatching classics of course! To help you out, we have conducted a list of the best romantic comedies of all time. Ready to take a trip down nostalgia lane?

What Are Romantic Comedies?

Romantic comedies are usually shortened as rom-coms. They are a popular genre of films and television shows that blend elements of romance and comedy. These stories typically revolve around the romantic relationships of the main characters and are characterized by lighthearted and humorous tones. Moreover, the main focus is on the ups and downs of the characters’ romantic journeys, with an emphasis on humor, witty dialogue, and situational comedy.

Common themes in romantic comedies include the development of romantic feelings, misunderstandings, obstacles to love, and ultimately, resolving conflicts leading to a happy and satisfying conclusion. The genre often explores the dynamics of relationships, love at first sight, second chances, and the comedic aspects of dating and courtship.

Best Romantic Comedies of All Time

These are our picks for the best romantic comedies of all time:

10. Love and Basketball – 2000

“Love & Basketball” is a romantic drama film released in 2000, written and directed by Gina Prince-Bythewood. The movie stars Sanaa Lathan as Monica Wright and Omar Epps as Quincy McCall. The story spans over a decade, following Monica and Quincy, who share a love for basketball from childhood. Living as next-door neighbors, they form a close bond and, as they grow older, discover their mutual passion for the sport. Both aspiring to become professional basketball players, they navigate their personal and professional lives while facing the challenges and complexities of their evolving relationship.

9. 13 Going on 30 – 2004

“13 Going on 30” follows the story of Jenna Rink, a 13-year-old girl who, after an awkward birthday party, wakes up the next morning in the body of her 30-year-old self (Jennifer Garner). Confused and disoriented, Jenna navigates her adult life, discovering the consequences of choices made and the true meaning of happiness and friendship. “13 Going on 30” incorporates a time-travel fantasy element. This allows Jenna to experience her future and gain insights into her younger self’s aspirations. The fantastical twist adds a unique and entertaining dimension to the romantic comedy.

8. 10 Things I Hate About You – 1999

“10 Things I Hate About You” is a romantic comedy film released in 1999, directed by Gil Junger. The movie is a modern adaptation of William Shakespeare’s play “The Taming of the Shrew.” (Well, as modern as 1999 can be!). The film revolves around two sisters, Kat (Julia Stiles) and Bianca (Larisa Oleynik), whose overprotective father has a rule that Bianca can only date if Kat does. To solve this dilemma, two boys, Cameron (Joseph Gordon-Levitt) and Michael (David Krumholtz), devise a plan to find a date for Kat. They enlist the mysterious and rebellious Patrick Verona (Heath Ledger) to win Kat’s heart and allow Bianca to start dating. As the plan unfolds, unexpected relationships develop, and characters discover the complexities of love and identity.

7. Love, Actually – 2003

“Love Actually” tells multiple interconnected love stories set in the weeks leading up to Christmas in London. The film explores various aspects of love, including romantic relationships, familial bonds, and unexpected connections between characters. The ensemble cast weaves together a tapestry of tales, each showcasing different forms of love and the universal emotions that come with it.

6. How to Lose a Guy in 10 Days – 2003

The story revolves around Andie Anderson, a magazine journalist writing an article titled “How to Lose a Guy in 10 Days,” and Benjamin Barry, an advertising executive. Andie bets that she can make a man break up with her within 10 days. However, Ben bets that he can make any woman fall in love with him in the same time frame. Unbeknownst to each other, they become the subjects of each other’s social experiments, leading to humorous and unexpected situations.

5. Bridget Jones’s Diary – 2001

“Bridget Jones’s Diary” is a romantic comedy film released in 2001, directed by Sharon Maguire. The movie stars Renée Zellweger as Bridget Jones, Hugh Grant as Daniel Cleaver, and Colin Firth as Mark Darcy (hotties alert!). Bridget decides to take control of her life by keeping a diary, where she documents her romantic misadventures, career struggles, and personal insecurities. As she navigates relationships with her charismatic boss Daniel Cleaver and the reserved lawyer Mark Darcy, Bridget discovers the importance of self-acceptance and genuine connection.

4. Eternal Sunshine of the Spotless Mind – 2004

“Eternal Sunshine of the Spotless Mind” (2004) is a romantic comedy with a sci-fi twist, directed by Michel Gondry and written by Charlie Kaufman. The story follows Jim Carrey’s character, who, devastated by a breakup with Clementine (Kate Winslet), opts for a procedure to erase memories of her. However, as his memories fade away, he discovers that he still harbors feelings for her, adding complexity to the narrative. The film explores themes of love, memory, and the enduring nature of emotions in the face of attempted erasure.

3. Mamma Mia! – 2008

“Love Actually” is a romantic comedy film released in 2003, written and directed by Richard Curtis. The film boasts an ensemble cast featuring Hugh Grant, Liam Neeson, Colin Firth, Emma Thompson, Keira Knightley, and many others. The film explores various aspects of love, including romantic relationships, familial bonds, and unexpected connections between characters. The ensemble cast weaves together a tapestry of tales, each showcasing different forms of love and the universal emotions that come with it.

2. 27 Dresses – 2007

“27 Dresses” is a romantic comedy film released in 2008, directed by Anne Fletcher. The movie stars Katherine Heigl as Jane Nichols. The story revolves around Jane Nichols, a perpetual bridesmaid who has served as a bridesmaid 27 times but has never been a bride herself. Jane’s life takes a turn when her younger sister Tess (Malin Åkerman) becomes engaged to the man Jane secretly harbors feelings for. Complications arise when Kevin Doyle (James Marsden), a cynical journalist, discovers Jane’s unique predicament and decides to write a feature about her experiences. As Jane navigates her sister’s wedding preparations, she finds herself facing personal revelations about love, friendship, and her own romantic aspirations.

1. She’s All That – 1999

The story follows high school student Zack Siler (Freddie Prinze Jr.), who accepts a bet to transform the “art nerd” Laney Boggs (Rachael Leigh Cook) into the prom queen within six weeks. As Zack takes on the challenge, unexpected connections, and genuine feelings develop between him and Laney. The film explores themes of social stereotypes, self-discovery, and the transformative power of love.

Is your favorite rom-com on the list? If not, what is the best romantic comedy of all time according to you?

You might also want to read: These Are the Most-Watched Movies Of the 2000s