Unlike other genres,romantic comediesthrive on predictabilityand take pride in being comfort food. The genre never claims to be realistic but focuses on building a universe between two individuals unlikely to get together. These relationships have changed over time as roles between men and women have evolved, as feminism gave female characters more agency in choosing their desired partner.When Harry Met Sally…took the genre several steps aheadas the characters were more than lovers.
They were individualistic, witty, vulnerable, and imperfect. Love did not remain an act of entrapment and sacrifice but became a worthy act of persuasion and a life-changing journey within the characters. The genre is not as profitable at the box office now as it used to be, but there still areplenty of romantic comediesthat are delighting audiences, from the teen LGBTQ+ romance ofCrush, the raunchy adult-orientedSleeping with Other Peopleor the classic throwback ofTicket to Paradise. Yet fans of the genre still nostalgic look back at the golden age of the decade. Here are ten films from the late ‘80s to the ‘90s that created a new-age happily-ever-after in the golden era of romantic comedies.
10Notting Hill (1999)
Two beautiful lead characters? Check. An impossible love story? Check. Quirky supporting characters? Check. Iconic romantic quotes? Check. Predictability? Cent percent!Notting Hillis the poster boy of the rose-tinted heydays of ‘90s romantic comedies. The film was directed by Roger Michell andstarred Hugh Grant as a bookshop owner, William Thacker, from Notting Hill, who falls in love with an American actress visiting his shop.
He is an average Joe from London, fading into the background of the city. His mundane life gets a kick after he meets the famous actress Anna Scott, played by Julia Roberts, who is struggling in her relationship with her boyfriend. After several unexpected kisses between the two, they fall in love with each other. However, they realize they come from two very different worlds. Interestingly, Richard Curtis wrote the film based on the real story of his friend who had a relationship with an actress visiting his store.
9When Harry Met Sally… (1989)
The genre-definingWhen Harry Met Sally…questions if a man and a woman can just be friends. The film stars Billy Crystal as Harry and Meg Ryan as Sally, who do not see eye to eye when they first meet. Harry is certain that two friends from the opposite sexes eventually get physically attracted to each other. Sally refutes the claim and is a believer inplatonic relationships between men and women. The film spans over 12 years to test the argument between the two characters, who eventually become friends but are confused about their feelings for each other.
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The film is known for its authentic characters as they were based on real-life conversations between director Rob Reiner, screenwriter Nora Ephron, and the film’s producer, Andrew Scheinman. The film changed romantic comedies as it had equally intelligent leading characters who stood by their convictions about relationships and formed an intimate friendship before they confessed their true feelings to each other.
8You’ve Got Mail (1998)
You’ve Got Mailmarked the beginning of virtual relationships depicted on screen and was directed by Norah Ephron. The filmstars Tom Hanks and Meg Ryan as online loversand offline professional rivals. Kathleen Kelly, played by Ryan, runs a small boutique bookstore, facing rivalry from a chain bookstore, Fox Books, that is newly set across the street. Joe Fox, played by Hanks, is the new bookstore owner and is despised by Kelly. The two meet anonymously on the internet and form an intimate relationship. Later, Joe finds out about Kelly and is faced with a difficult decision.
The story was based on the Hungarian playParfumerieand was the third film starring Ryan and Hanks as romantic leads. The film also stars Dave Chappelle as Joe’s best friend and as the branch manager of his bookstore.You’ve Got Mailalsopayshomage to the thankless passion of independent bookstores, which often get overshadowed by capitalist bookstore chains.
7Sleepless in Seattle (1993)
Sleepless in Seattleis another directorial by Ephron, with Meg Ryan and Tom Hanks playing love interests. In this film, Ephron moves awayfrom the vibrant characters of New Yorkand focuses on melancholic loners from Seattle. Hanks plays Sam, who is a widowed architect and a single parent. He goes on a radio talk show and expresses how he misses his wife as his son seeks a new partner for his lonesome father.
It touches several listeners, including a journalist named Annie, played by Ryan, who gets in touch with him. She is falling out of love with her relationship. The couple initially share a few misunderstandings, making them admire each other from a distance. The lovers formally connect at the end, making it one of the rare romantic comedies shedding light on mutually unrequited love.
6Pretty Woman (1990)
Pretty Womanadapts Cinderella to ‘90s Hollywood. The iconic film was directed by Garry Marshall and starred Julia Roberts as Vivian, a prostitute who hustles in the red-light district on Hollywood Boulevard. She meets Edward,played by Richard Gere, a corporate raider who visits Los Angeles on a business trip. He is emotionally starved in his materialistic life and finds company through Vivian. Edward pays her for her company instead of her usual service, beginning an unusual relationship between the two. Vivian gets a taste of his world and his luxury, posing as his girlfriend, but begins questioning the transactional nature of the relationship.
The film was initially written as a dark story of a prostitute’s life and drug abuse but was turned into a big-budget romantic comedy. In retrospect, the adapted changes shed more empathetic light on the life of an adult entertainer by turning her into an engaging character, as opposed to fetishizing the dark tales from the streets of Hollywood.
510 Things I Hate About You (1999)
The cult classic10 Things I Hate About Youis a modern-day adaptation of Shakespeare’s playThe Taming of the Shrew.The film launched the successful careers of Julia Stiles, Heath Ledger, and Joseph Gordon-Levitt, who played high schoolers from Seattle. Kat, played by Stiles, is the elder sister of Bianca. She is unlike other girls in high school and is difficult to approach.
This makes it difficult for Bianca to date the popular guy, as her father doesn’t want her to date until Kat has a boyfriend. Kat is tricked into falling in love with the equally repulsive Patrick as she fights her feelings. The film is known for staying true to theShakespearean themes of manipulation, drama, and deceitwhile staging its premise in an American high school.
4My Best Friend’s Wedding (1997)
My Best Friend’s Weddingis another addition to Julia Robert’s famed filmography portraying complicated women.Roberts plays Julianne Potter, a food critic nearing her 30s. She and her childhood friend, Michael, had a pact to marry each other if they remained single by age 28. She gets the shocking news of Michael getting married to a 20-year-old daughter of a wealthy man. Julianne alleges he is making a mistake and rushes to wreck the wedding. However, she finds out she is appointed the maid of honor, complicating her plan.
The film is known for its dream-like soundtrack, which includes covers of popular wedding songs common to several romantic comedies of the era.Roberts shone in her comic timingand added emotional depth to her portrayal of the desperate Julianne.
3Four Weddings and a Funeral (1994)
Four Weddings and a Funeralstars Hugh Grant as a handsome but unlucky Englishman named Charles, who has a hard time with the ladies and shares the same predicament with his friends. He meets Carrie at a wedding, and it is love at first sight. They spend the night together but part the next day. The couple admits they are making a grave mistake not seeing each other.
The two meet at different points in their life in multiple events, which includes four weddings and a funeral. They are never on the same page and are committed to different relationships. However, they grab the chance and unite when life gives them the last window of opportunity. The film has several laugh-out-loud moments, andGrant brings the hidden lonelinessinto the much-celebrated exuberance of men’s bachelorhood.
2Clueless (1995)
Cluelessis the perfect romantic comedy from a millennial’s point of view. The film stars Alicia Silverstone as Cher, a popular girl from high school in Beverly Hills. She is the quintessential rich spoilt brat constantly bickering with her ex-stepbrother Josh. She may not be the brightest, but she sees herself as the perfect matchmaker. She persuades two teachers to get hooked and gives the clumsy new girl, Tai, a new makeover.
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Accidentally, Tai gets more popular than Cher, which enrages her. Amongst all the yes-men in Cher’s life, Josh is her only critic who disapproves of her choices in men and her actions. Later, she realizes Josh is the only person who wants her best and falls in love with him. The relationship is unusual but is an excellent example of howunapologetic fictional relationships were in the ‘90s.
1Jerry Maguire (1996)
Jerry Maguireblends entrepreneurial spirit with romance in a witty story starring Tom Cruise as the titular character. Maguire is a sports agent and works for a massive sports management firm. After one of his clients gets severely injured, he is inspired to write a memo urging the company to rethink its morals regarding caring about its clients and not focus on profit. It gets him fired, and he is forced to work pro bono. He is accompanied by his firm’s accountant, Dorothy,played by Reneé Zellweger.
She is a single mother in her 20s and misses out on the adventure other 20-year-olds usually enjoy. Maguire and his new professional venture fill in this gap. They form a relationship that does not start on the right terms, leading to their brief amicable breakup. However, after Jerry has a successful night in his business, he returns to Dorothy, confessing his weakness for her in a few of the most iconic romantic dialogues from the world of romantic comedies.
One of the most consistent tropes during the golden age of rom-coms is the ‘enemies to lovers’ storyline, so if you’re looking for more great romantic comedies, check out our five favorite films which see enemies become lovers:
