25 Best Romantic Comedies of All Time

50 First Dates is a 2004 romantic comedy starring Adam Sandler and Drew Barrymore. Sandler plays Henry Roth, a man who falls in love with a girl named Lucy, Barrymore. However, after a devastating car accident, Lucy loses her memory from anything after the accident each day. 

Each day, Henry Roth continues to win Lucy over, even though she never remembers him. Though it is hard work, Henry sticks with Lucy because their love is so pure and all-encompassing. This kind of unfaltering effort and dedication to their love is the reason people watch rom coms, making 50 First Dates one of the best romantic comedies of all time. 

The Holiday is about two women who swap homes during the holiday season and fall for local men. Starring Cameron Diaz and Kate Winslet, The Holiday is not only a Christmas classic but also one of the best romantic comedies of all time. 

This Nancy Meyers movie gives fans of romantic comedies exactly what they want, picturesque settings and swoon worthy characters. From Jude Law’s tender portrayal of fatherhood to Jack Black’s funny and sweet friendship, these men are clearly written by a woman and it makes the film all the better.  

27 Dresses is the story of a woman who has been a bridesmaid 27 times but never the bride, longing to find love herself. When a journalist uncovers this bizarre story, he pursues it, and her. 

This beloved film starring Katherine Heigl and James Marsden has become something of a classic within the romantic comedy genre. It is full of classic tropes such as the hopeless romantic searching for love and the writer who falls for his subject. 

However, 27 Dresses is also incredibly funny and heartwarming, leaving you to feel hopeful and all fuzzy inside, the ultimate objective of movies like these. 

The 2009 romantic comedy The Proposal stars Ryan Reynolds as Andrew Paxton, the assistant to high-powered book editor Margaret Tate, played by Sandra Bullock. The two pose as married so Margaret is not deported to Canada. 

Not only is The Proposal a classic enemies to lovers film, but it is witty, tender and full of draw dropping chemistry. 

Though the film may come off as a bit cheesy and cliche, it has won over many viewers’ hearts with its more emotionally deep topics. Andrew and Margaret’s relationship is also quite touching, as they bring out the best in each other. It is also very endearing to see the way Andrew sticks with Margaret during her incredibly illegal scheme, learning to love her quirks along the way. It is Reynolds’ and Bullock’s raw, genuine characters that make The Proposal one of the best romantic comedies of all time. 

Clueless, starring Alicia Sliverstone and Paul Rudd, is a classic 1995 teen romantic comedy that has remained a fan favorite over the past almost 30 years. The film follows a beautiful and popular high school student named Cher who makes a new friend and decides to give her a makeover while also setting up two teachers from her high school. 

Alicia Silverstone’s portrayal of Cher is absolutely iconic with her hit catchphrase “As if!” The film is so loved by fans, it even inspired a musical of the same name, featuring Dove Cameron as Cher. 

13 Going on 30 is a 2004 rom com starring Jennifer Garner and Mark Ruffalo. The film follows a 13 year old girl who makes a wish to be thirty, flirty, and thriving. However, she wakes up the next morning as her 30 year old self. 

Jennifer Garner plays this role flawlessly, capturing the innocence of a young girl in an adult woman’s body. The film also does a phenomenal job displaying love at its most pure form; stemming from a childhood friendship. 13 Going on 30 is one of the most heartwarming films out there and easily one of the best romantic comedies of all time. 

Related: 13 Best Jennifer Garner Movies, Ranked

Crazy Rich Asians is a newer romantic comedy, but equally deserving of its spot on this list. Released in 2018, this film follows Nick and Rachel when Nick takes Rachel to Singapore for a wedding and to meet his family. 

This film is not only filled with some of the most tender, beautiful love one can see in a film, but it is also just incredibly fun. As the film revolves around the wealth of Nick’s family, Crazy Rich Asians is lavish and daring, full of stunning scenery and sets. The movie is also full of charismatic and lovable characters you will not forget. 

The Wedding Singer is a 1998 romantic comedy starring Adam Sandler and Drew Barrymore. The film is about a wedding singer who falls in love with an engaged waitress. 

This beloved 80s rom com is easily one of the best romantic comedies of all time. Not only does it put on display Adam Sandler and Drew Barrymore’s undeniable chemistry (this is the second movie of theirs on this list), but it is also incredibly funny. On top of this, The Wedding Singer is a definitive movie in the romantic comedy genre. It is the blueprint for many films to come. 

While You Were Sleeping is about a hopeless romantic Chicago Transit Authority ticket booth operator who is accidentally mistaken for the fianceé of a comatose patient. 

As one of Sandra Bullock’s first hit films, While You Were Sleeping is seen as one of her best. The film is well written and incredibly funny, continuing to draw in viewers for the past 30 years. 

Also, if you are specifically interested in romantic comedies that take place in Chicago, this is definitely one you should check out. 

How to Lose a Guy in 10 Days is a 2003 romantic comedy starring Kate Hudson and Matthew McConaughey. The film follows an advertising executive, McConaughey, who bets that he can make a woman fall in love with him while a writer, Hudson, is writing a story about women scaring men away. 

The writing in How to Lose a Guy in 10 Days is smart and witty, capturing the hearts of lovers and haters of rom coms alike. Also, if you are searching for top-notch on-screen chemistry, Matthew McConauhey and Kate Hudson’s chemistry is some of the best out there. 

Read More: Why How to Lose a Guy in 10 Days Is Popular Again

Love Actually, a 2003 romantic comedy, follows the lives of eight different couples at Christmas time. The movie stars some of the most iconic actors and actresses such as Hugh Grant, Colin Firth, Keira Knightly, and Emma Thompson. 

Love Actually is a pioneer in the world of rom coms, especially with interconnecting storylines; it masterfully weaves together the lives of  over 10 characters. Along with this, Love Actually is witty and tender, encapsulating realistic versions of love, making it one of the best romantic comedies of all time. 

The 1997 romantic comedy, My Best Friend’s Wedding, starring Julia Roberts, Dermot Mulroney, and Cameron Diaz, follows Julia Roberts’ character when her life-long best friend gets engaged and she realizes that she is in love with him. 

My Best Friend’s Wedding is a tear-jerker of a romantic comedy but has become a classic film within the genre. It is funny, amusing, and charismatic. You may not always like Roberts’ character but you can definitely sympathize with her. 

Related: 25 Movies Like My Best Friend’s Wedding and Where to Stream Them

Crazy, Stupid, Love is a 2011 film about a middle-aged man (played by Steve Carell) whose wife asks him for a divorce. In a search to reclaim his manhood, he befriends a ladies man at the bar to teach him how to pick up girls. 

Though the film is not too old, Crazy, Stupid, Love has become a household name in the rom com genre and is easily one of the best romantic comedies of all time. Like Love Actually, Crazy, Stupid, Love has many interconnecting plots that all weave together in the end. 

Packed with an iconic cast of actors such as Ryan Gosling, Emma Stone, Julianne Moore and more, this film is an immediate must watch if you have not seen it yet. 

Read More: 7 Movies Like Crazy Stupid Love 

It Happened One Night is the oldest film on this list but definitely one of the best romantic comedies of all time. From 1934, the film follows a reporter trailing a runaway heiress on a bus from Florida to New York. However, when the bus leaves them behind, they become stuck with each other. 

It Happened One Night is a classic film and it portrays one of the most classic tropes: Forced proximity. It is films like It Happened One Night that laid the groundwork to make the romantic comedy genre of films as successful as it is today. 

Pretty Woman is a 1990 romantic comedy starring Julia Roberts and Richard Gere. The film follows a man who hires a prostitute for the week but ends up falling for her, despite the different worlds they live in. 

A modern Cinderella story, this romantic comedy displays a message we are all searching for; people are able to see our true selves and our full potential in spite of our differences. Though Julia Roberts’ character is judged by some, Gere’s character sees through this and fully embraces her personhood. 

My Big Fat Greek Wedding is a 2002 romantic comedy about a young Greek woman who falls in love with a non-Greek man and then has, as the title suggests, a big, fat, Greek wedding. 

My Big Fat Greek Wedding deservedly earns its spot as one of the best romantic comedies of all time. It is funny, tender, and very Greek! It masterfully represents the importance of navigating your family and their expectations, while placing value in your own happiness. Plus, the love between the two main characters, Toula and Ian, is definitely one for the books. That is why the original film got a second and third movie! 

What’s Up, Doc? is a 1972 romantic comedy starring the one and only Barbara Streisand. The film is about the accidental mix-up of four identical plaid bags, leading to many wild instances. 

What’s Up, Doc? brings the comedy to romantic comedies, leaving a lasting impact on the rom coms to come. If you are looking for some of the most definitive films in the history of romantic comedies, this is definitely one you should check out. 

Groundhog Day is a 1993 film about a self-centered weatherman who finds himself in a loop on Groundhog Day. 

Groundhog Day is the rom com for the people who claim to not like rom coms. It is the perfect film to warm a cynic’s heart, portraying the emotional growth of Bill Murray’s narcissistic character through love. The element of the time loop also makes this romantic comedy a unique watch. 

Sleepless in Seattle is a 1993 Nora Ephron film starring Tom Hanks and the queen of rom coms herself, Meg Ryan. The film follows a recently widowed father whose son calls into a radio show in an attempt to find his father a partner. 

Sleepless in Seattle is a beloved classic for romantic comedy fans. Not only is the film full of heart and wit, but it is also packed with stunning scenery that takes the film an extra mile. Sleepless in Seattle is widely acknowledged as one of the best romantic comedies of all time and it definitely fits that mark. 

10 Things I Hate About You is a 1999 teen film, but it has become known as one of the best romantic comedies of all time. Starring Julia Stiles and Heath Ledger, the film follows a high school boy who wants to date a girl named Bianca. However, Bianca can’t date unless her sister Kat does. So, school rebel Patrick is employed to date Kat so that her sister can go on a date. 

Though 10 Things I Hate About You is about high school love, the film is very raw and emotional, really digging deep into the character of both Kat and Patrick. The film defies stereotypes and creates new rules and boundaries about love. 

The script is also incredibly sharp and witty, drawing in viewers of all ages to this timeless film. 

Four Weddings and a Funeral is a fan favorite of Hugh Grant’s many successful romantic comedies. The 1994 film follows a committed bachelor during five social events, four weddings and one funeral, as he realizes he is falling in love. 

Not only is this the film that made Hugh Grant a household name, but Four Weddings and a Funeral is also considered one of the best British films ever. Loved for its cast of witty, British characters along with being genuinely moving and incredibly poignant, Four Weddings and a Funeral is one of the best romantic comedies ever made. 

Roman Holiday is a 1953 romantic comedy starring Audrey Hepburn. The film follows a sheltered princess who escapes her guardians and falls for an American news reporter in Rome. 

This film is the blueprint for countless films to come and is universally known as one of the best romantic comedies of all time. Not only is the essence of a Roman vacation whimsical and nostalgic, but the chemistry in the film is also undeniable, making it a timeless classic. 

Read More: Ranking the Best Audrey Hepburn Movies from Musicals to Thrillers

Notting Hill, starring Julia Roberts and Hugh Grant, two actors who have numerous films on this list, is a 1999 romantic comedy about an American actress who falls for a quirky but endearing travel bookstore owner in the London neighborhood of Notting Hill. 

Not only is Notting Hill witty, sharp and heartwarming, but it also has one of the most famous professions of love in any movie out there. She was just a girl, standing in front of a boy, asking him to love her. What could go wrong? 

You’ve Got Mail stars two household names on this list, Meg Ryan and Tom Hanks. The film is about a book superstore magnate and an independent bookshop owner who fall in love anonymously on the internet. 

You’ve Got Mail is so universally loved because it is full of tension. Tension between Hanks and Ryans’ characters as their bookstores are competing with one another. Tension because their characters are falling in love with a mysterious person. And tension from viewers who know that they are falling for their competitor. You’ve Got Mail is incredibly smart and sharp, along with heartwarming and nostalgic, making it one of the best romantic comedies of all time. 

Finally, number one on this list of the best romantic comedies of all time is When Harry Met Sally… When Harry Met Sally… follows two friends over many years and their growing relationship. 

When Harry Met Sally… is universally known as the greatest romantic comedy of all time and deservedly so. The film is the blueprint for friends to lovers and depicts love as a bond that is more than just sex; it is a partnership for life. Harry and Sally truly depict this and beautifully portray all encompassing love, continuing to warm the hearts of viewers for the last 35 years.