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10 Best Rom-Coms of the 90s

5 min read

As we head towards the most romantic day of the year, we thought we'd continue to escape from the doom and gloom of reality by travelling all the way back to the nineties. Things were much simpler then, right? Back then, love wasn't determined by whether you'd been Super-Liked on Tinder, oh no! Your true love was found in the magical prediction of origami; “go on, pick a number, pick a colour!”

So let's set our minds back to the days of our younger innocence and find hope in some of the most wholesome and romantic movies of the decade. The nineties are making a comeback, so grab your Walkman and your Motorola because this nostalgia's going to hit you like a tonne of bricks.

10. You've Got Mail (1998)

We commence our countdown with a charming story of turn-of-the-century online dating. and shine in 's You've Got Mail, the tale of two rival booksellers falling in love. Whilst we live in a time of “fast” everything, from fast fashion to fast delivery, it's revealing to hear of Katherine's (Ryan) struggles as an independent bookstore owner, while Joe (Hanks) thrives as the owner of a chain. Their online relationship, however, is blossoming – an enlightening look at the start of cyberdating. You've Got Mail has its issues but is also amiable; the reasoning for its number ten position.

9. Sleepless in Seattle (1993)

Hanks' and Ryan's previous endeavour five years earlier sees them in another of Nora Ephron's romantic retreats. This time dealing with the role of bereavement in certain romances, Hanks plays Sam, a widower who moves to Seattle with his young son. After opening up to his struggles on live radio, the heartstrings of America are pulled – along with Annie (Ryan). Ephron keeps the strings of the film loosened throughout, keeping the pair's love distant, but growing closer together as the film progresses. Sleepless in Seattle finds the intimacy in distance and the love within loss. It takes our ninth spot as a tender reminder of the imperfections of love and relationships.

8. Never Been Kissed (1999)

's immeasurable warmth glows in Raja Gosnell's Never Been Kissed. Barrymore plays Josie, a 25 year-old copyeditor who goes back to high school to report undercover for the local newspaper. In the hopes that she can get it right the second time around, Josie tries desperately to get in with the popular crowd and have her first kiss. Coupled with cringe-fest high school flashbacks and comic relief of supporting actors, Josie finds romance with young English teacher, Mr Coulson (Michael Vartan). Never Been Kissed has charisma and a big heart, held up by Barrymore's infinite talent.

7. There's Something About Mary (1998)

Following on from their 1994 hit comedy Dumb and Dumber, the Farrelly Brothers try on romance for size, with their usual tastes still at play. Starring Cameron Diaz, Ben Stiller and Matt Dillon, the film follows Ted (Stiller) who, years after being asked to prom by the high school knockout, Mary (Diaz), has a second chance with his first love. Keeping in touch with their well-known explosive slapstick-esque jokes, the Farrelly Brothers pull another gag-fest out of the bag. Although it leans more towards comedy than romance, it has its touching moments.

6. Clueless (1995)

Cult-classic Clueless has made its way back into the spotlight in recent months with the fashion and culture trends of this 1995 hit proving to be once again popular. Cher Horowitz is a cult icon, two-piece plaid skirt suits are ‘a look' and Paul Rudd is… well, Paul Rudd. Directed by Amy Heckerling, Clueless is a coming-of-age high school comedy where self-assured brats stumble their way to maturity, finding romance along the way. With a story loosely based on Jane Austen's Emma, matchmaking Cher realises that her own love life is rather confused and finally starts to seek out what she wants. After 25 years, Clueless still achieves top-end reviews, with lifelong fans and newcomers loving it wholeheartedly.

5. Four Weddings and a Funeral (1994)

's Four Weddings and a Funeral sparked a series of film collaborations between and screenwriter, , turning Grant into the 90s heartthrob he's so famously known for. The film is perhaps most notable for its iconic “is it still raining? I hadn't noticed…” scene, performed beautifully by Andie MacDowell along with Grant as Charles and Carrie. The pair's love blossoms throughout the film's five social occasions, along with the heart-warming stories of their supporting cast. It's a film that exudes 90s nostalgia and is oh-so-very British.

4. 10 Things I Hate About You (1999)

Shakespeare for the cool kids. This loose Taming of the Shrew adaptation has won over the hearts of many since it's release in March 1999. Partially for its handsome young cast (, , Joseph Gordon-Levitt, Larisa Oleynik) but also for its heartfelt writing and narrative. Cameron (Levitt) cannot date Bianca (Oleynik) until her ill-tempered older sister, Kat (Stiles) does. Cameron pays the mysterious Patrick (Ledger), to charm Kat, and the pair unknowingly catch feelings. 10 Things I Hate About You is a rom-com for those who don't like romance. Just like Kat, you won't expect to fall in love with it, but trust me – you will.

3. Pretty Woman (1990)

makes her first appearance in our number three spot, starring alongside in Garry Marshall's 1990 film. Pretty Woman follows Edward (Gere) and Vivian (Roberts), a pair who unexpectedly fall in love after Edward hires Vivian for her escort services. Although its plot may seem more adult, it is perhaps one of the most innocent rom-coms around, glowing with sweetness and delicacy. Pretty Woman is one of the top-grossing romantic comedies of all time and it ultimately created the backbone of the modern and its place at number three is testament to this.

2. Notting Hill (1999)

Almost a decade later, Roberts stormed the British box office alongside Hugh Grant in Roger Mitchell's Notting Hill. William (Grant) a bookseller, meets and falls in love with Anna (Roberts), a renowned American actress. In this contemporary British fairytale, William and Anna must face the obstacles of their opposing social statuses to find true love. Writer, Richard Curtis includes the same charm seen in Four Weddings and a Funeral and marks Notting Hill as a delightfully sweet-tempered flick with an air of bright, gawky charisma. It takes second place for its perfectly witty and likeable character.

1. Before Sunrise (1995)

Our list concludes with 's stunning 1995 film starring and . While travelling by train through Europe, Jesse and Celine meet. Jesse soon decides to spend his remaining hours in Europe with her before returning to the US. This enthralling feature has captured hearts across the globe for over two decades, leaving many wondering if the couple would meet again after one night of passionate conversation on the streets of Vienna. Of course, the ‘Before Trilogy' has since concluded with Before Sunset (2004) and Before Midnight (2013) providing a suitable ending to the flourishing relationship of Jesse and Celine. Before Sunrise is so ordinary and yet simply spellbinding, seeing time unfold for the pair and knowing that tomorrow will soon come.

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