Mad About The Movies: The Best Romcoms Of The Past 25 Years

February is a time for romance – and that includes at the cinema. 

Valentine’s is the perfect time for catching up on romcoms and with the most recent release of the fourth Bridget Jones movie, Mad About the Boy (2025), it’s clear that our beloved romantic comedies are here to stay. 

Premiering on February 13, Mad About the Boy has raked in upwards of $35.5 million internationally, with its largest market being in the United Kingdom and Ireland.

The movie follows Jones trying to navigate her love life after having two children and losing her husband. Naturally, fans have started comparing the new film to the beloved original, Bridget Jones’s Diary (2001).   

Romcoms may have changed over time but our love for them hasn’t. Here are a few of STELLAR’s favourites from over the past 25 years. 

2001 – Bridget Jones’ Diary 

The film that started it all follows the awkward and confused Jones, as she tries to navigate her love life. Her life begins to drastically change as two potential suitors enter it, and she keeps a diary and documents her most embarrassing and relatable moments.

Released in April of 2001, the film was a massive commercial success, managing to make a total of $282 million worldwide. 

The beginning of the Bridget Jones franchise marked an increase in quirky, awkward and relatable main characters in romcoms, a trope that audiences continue to find endearing.  

2003 – How to Lose a Guy in 10 Days 

How To Lose A Guy In 10 Days follows journalist Andie Anderson, as she tries to prove that certain behaviours are a surefire way to scare potential love interests away. To prove her point, she recruits Benjamin Barry as a clueless test subject. Little does she know, he’s playing her at her own game. 

This film inspired an era of romcoms where the leading woman was not only dedicated to love, but also to her job. Kate Hudson’s character pioneered a feministic approach to modern love stories, which starkly contrasted the damsel in distress ideal of previous years. 

2008 – 27 Dresses  

Jane Nichols has attended 27 weddings where she had been the bridesmaid, never the bride. One night, she even attends two simultaneously while trying to keep her secret undiscovered.

Unfortunately for her, her plan falls into the hands of writer Kevin Doyle, who plans on featuring her in his next article. The film follows the pair and their contrasting views about life and love, alongside their relationship that begins to evolve. 

This film also features a career driven woman, a direct effect of the previous film which helped pave the way for this sub-genre.  

2011 – Crazy, Stupid, Love 

Cal Weaver, a soon to be divorcee, fights to keep his marriage alive after losing his wife to a coworker. He meets Jacob Palmer who begins to give him tips and tricks on how to win over his wife again. The movie navigates both their struggles and successes in their respective relationships. 

One of Ryan Gosling’s many entires into the world of romance, this film turned the romcom genre on its head, instead focusing on male desire and needs.

2018 – To All the Boys I’ve Loved Before 

Sixteen-year-old Lara Jean Covey, a hopeless romantic, has fallen in love with five people over the course of her life. Being too shy to act on these crushes, she writes each of them a letter confessing her love. Her life comes to a crashing halt when she discovers all five letters have been delivered to their unintended recipients. 

To All The Boys premiered in 2018 on Netflix and has spanned multiple sequels. The worldwide streaming release meant that this film was accessible to so many more audiences, particularly the YA demographic. Young adult has since become a major cohort for romcoms. 

2023 – Anyone But You 

Bea and Ben have an instant connection after meeting in a coffee shop. They spend the day together and the next morning she leaves without saying goodbye. Their paths cross six months later, where they decide to fake being in a relationship. 

Premiering in December of 2023, Anyone But You became known as the film that reignited the romcom genre. It made a gross profit of $220 million worldwide, and Glen Powell and Sydney Sweeney’s off-screen chemistry became a masterclass in romcom marketing. 

Words by Emma Nolan