The 7 Most Underrated Romance Movies of the 2000s, Ranked, Read Now

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Romance movies were very popular in the 2000s. At this time, popular films like Mamma Mia!, Love Actually, Pride & Prejudice, and The Notebook emerged; they all went on to become commercial successes at the global box office and are still warmly recalled years later. Even more modest independent romances, like as (500) Days of Summer, Juno, and Eternal Sunshine of the Spotless Mind, were popular with general audiences and are still warmly recalled today.

But not every romantic movie from the 2000s received the praise and acknowledgment it merited. Some did not perform well at the box office, some received unfair criticism, and some have gotten lost in the passage of time. With love returning and Valentine’s Day approaching, being in the air, here’s a look at the most underrated romance movies from the 2000s.

7 Underrated Romance Movies Of The 2000s

7. Imagine Me & You (2005)

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The 2005 romantic comedy Imagine Me & You, directed by Ol Parker, the guy behind Mamma Mia! Here We Go Again and Ticket to Paradise, follows Rachel (Piper Perabo) as she gets ready for her wedding to Hector (Matthew Goode) and ends up falling in love with the florist, Luce (Lena Headey). Things start to get problematic for all three of them when she gets married while having affections for this new woman. The supporting cast of the movie features Darren Boyd, Celia Imrie, Anthony Head, and Sharon Horgan, most of whom are from Britain. It got generally negative reviews and barely made $2.6 million at the box office.

6. My Blueberry Nights (2007)


In My Blueberry Nights, singer Norah Jones plays Elizabeth, a lady who travels throughout America and meets many people, each with their own interpretation of love. This is Jones’s debut acting role. The movie, which was based on Wong Kar-Wai’s 2001 Chinese-language short film In the Mood for Love, was his debut American feature film. The characters Elizabeth meets are portrayed by Jude Law, Natalie Portman, Rachel Weisz, and David Strathairn. Critics gave the movie a mixed response overall.

5. Zack and Miri Make a Porno (2008)


Zack and Miri Make a Porno, the highly regarded cult classic Kevin Smith’s largest attempt at a mainstream comedy, broke from the narrative of his previous films, such as Clerks, Mallrats, and Jay & Silent Bob Strike Back. Starring as Zack and Miri, respectively, are Seth Rogen and Elizabeth Banks, two high school pals who decide to shoot a pornographic film to gain money after they fall behind on their payments. They discover they have feelings for one other while assembling a colourful ensemble of characters for their film.

4. Kissing Jessica Stein (2001)


The independent romantic comedy from 2001 Smiling Jessica Stein is a highly recommended LGBTQ+ film from the 2000s. The film, which was written and directed by Charles Herman-Wurmfeld and starred Jennifer Westfeldt and Heather Juergensen, centres on Jessica (Westfeldt), a woman who feels compelled to find a husband and settle down, but instead begins to fall in love with Helen (Juergensen). Despite having a $1 million budget, Kissing Jessica Stein made $10 million at the global box office.

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3. Definitely, Maybe (2008)


In that it centres on a single father named Will (Ryan Reynolds) telling his ten-year-old daughter Maya (Abigail Breslin) about his three most significant relationships, Definitely, Maybe is similar to How I Met Your Mother in that it challenges the viewer to identify which of the three women (Rachel Weisz, Isla Fisher, and Elizabeth Banks) is Maya’s mother. The majority of the movie is portrayed through flashbacks, and to avoid discussing sex explicitly, clever metaphors are employed. Adam Brooks, whose previous film credits include Bridget Jones: The Edge of Reason and Wimbledon, wrote and directed it.

2. Love & Basketball (2000)


Gina Prince-Bythewood made her directing debut with Love & Basketball. She has since directed films such as The Woman King, The Old Guard, and The Secret Life of Bees. The film follows the lives of two next-door neighbours who have known each other since they were young and are following their individual basketball careers before falling in love. Quincy McCall (played by Mike Epps) and Monica Wright (Sanaa Lathan) are the subjects of the film. The movie provides an intimate look at two friends opening up to what’s in front of them, as well as an epic romance spanning years.

1. Punch-Drunk Love (2002)


Punch-Drunk Love, a romantic comedy-drama directed by Paul Thomas Anderson, was an unexpected pick to follow up 1999’s Magnolia. Adam Sandler plays Barry Egan in the movie, a lost and lonely man with social anxiety whose life transforms when he meets Emily Watson’s character Lena Leonard and falls in love. But when Barry makes a phone call to a sex line that has unexpected effects, his bad habits put his happiness in jeopardy. Punch-Drunk Love was a box office disaster even though critics gave it mostly favourable reviews.

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The 7 Most Underrated Romance Movies of the 2000s, Ranked
The 7 Most Underrated Romance Movies of the 2000s, Ranked