Rom-Com Nostalgia: Revisiting the Best Movies of the 90s and 2000s

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There’s a certain charm and warmth in the old rom-com movies that seems to be missing in today’s romantic comedies. The cozy settings and lovable characters make the classics stand out. Check out this list for an epic binge-watching session with these top picks:

How To Lose A Guy in 10 Days

 In this movie, two people who date each other as a ruse end up falling in love. Benjamin Barry, an advertising executive, makes a bet that he can make any woman fall in love with him to win a business deal. Meanwhile, ambitious magazine writer Andie Anderson is tasked with writing a groundbreaking article about what makes men break up with women.

Despite their initial motives, they end up genuinely caring for each other. This lighthearted movie follows quirky characters in playful situations. Kate Hudson’s irresistible charm and Matthew McConaughey’s natural allure make this movie more enjoyable.

50 first dates

The movie follows Henry Roth (Adam Sandler), a marine veterinarian who avoids commitment by only dating tourists. His life undergoes a drastic change when he encounters Lucy Whitmore (Drew Barrymore), an art teacher, and finds himself falling in love with her. Just when he thinks he’s finally found the girl of his dreams, he discovers that she has short-term memory loss.

Every day, all her memories are erased as she goes to sleep. However, he’s willing to go to any lengths for her and finds creative ways to win her over again and again. Set in a small coastal town packed with sea animals, this movie is sweet and lighthearted.

Sweet Home Alabama (2002)

Everything in Melanie’s life is perfect, a small-town girl who has become a renowned fashion designer in New York. She’s also proposed to by the most eligible bachelor. But she has skeletons in her closet and must return to her hometown, Alabama, to fix her past that threatens to ruin her lifestyle, such as getting a divorce from her ex-husband, Jake, who was her high school sweetheart. Jake repeatedly refuses to divorce her.

Determined to get a divorce, she attempts to make his life difficult in order to persuade him. However, everything changes when she reconnects with her roots and the long-buried feelings for Jake rekindle. This is a sentimental movie full of witty banter and Reese Witherspoon’s charismatic performance is another reason to watch it. 

My Best Friend’s Wedding

In this movie, we follow Jules, played by the iconic Julia Roberts, who receives a phone call from her lifelong best friend, Michael, informing her that he is getting married. Long ago, they made a pact that if they remained unmarried by the age of 28, they’d marry each other. Realizing that she is in love with him, she resolves to sabotage his wedding.

Things are further complicated when she reaches the wedding venue and his fiancée, played by Cameron Diaz, asks her to be her bridesmaid. This heartfelt film explores the moral dilemma of Jules as she comes to terms with her feelings.

The Runaway Bride

Another romantic comedy starring Julia Roberts features a spirited woman named Maggie who is known as the “runaway bride” because she keeps leaving all her grooms at the altar. A reporter named Ike Graham writes a misleading article about her and gets fired after Maggie sends angry remarks to the newspaper editor.

Determined to get his job back, Graham goes to her hometown to verify the facts. Initially, they find each other insufferable, but everything changes when he takes the time to genuinely understand her, leading to an unexpected connection.

Definitely, Maybe

This movie explores the life of Will Hayes, a man in his 30s who is in the midst of a divorce from his wife. One day his 10-year-old daughter asks to know the story of how her parents met. Will recollects his past relationships with three significant women in his life, without revealing their real names, leaving his daughter to guess which one is her mother.

As he reflects on these relationships, will realizes that he still has unresolved feelings for one of those women. This heartfelt movie examines the impact that one’s choice of partners can have on their life. 

The Proposal

Set in New York, Andrew has been grinding away as an assistant to a demanding editor Margaret Tate, a Canadian, who is known to have a harsh demeanor with her clients and faces deportation when her visa expires. To save her position as a chief editor, she orchestrates the plan of a fake marriage with Andrew, convincing him with the promise of career advancement; reluctantly, Andrew agrees. However, a skeptical INS agent plans to test them on each other the following Monday.

As Andrew has to leave for his hometown for his grandma’s 90th birthday, Margaret accompanies him there. This trip irrevocably alters her, when she gets to know the real Andrew for the first time. Forced to fake a relationship, they end up developing genuine feelings for each other. This heartwarming film is laced with humor, and Sandra Bullock and Ryan Reynolds’ performances are captivating, making it difficult not to like this movie!

Watch the trailer here.

Clueless

This must-watch romantic comedy is a loose adaptation of Jane Austen’s “Emma.” Cher is a rich, popular, and fashionable girl who lives with her father and her stepbrother. She loves to meddle in other people’s lives and play matchmaker, believing she is doing them a favor, without knowing any better. When a new student arrives at her school, she decides to give her a makeover and transform her life.

Cher has a complicated relationship with Josh, her stepbrother, who thinks she is self-centered. However, as Cher slowly recognizes her flaws and undergoes a transformation, both of them gradually develop feelings for each other.

See Also

Preety Dhunna is a dynamic content writer with a background in English literature and an unwavering passion for storytelling. She combines thoughtful analysis with engaging narratives to make nuanced topics accessible and interesting. With meticulous research and editing, Preety ensures her work is both informative and compelling. When not immersed in writing or lost in a book, she enjoys creative pursuits like embroidery.

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