15 Underrated Romantic Movies With Well-Known Actors

Definitely Maybe

Many of your favorite stars have probably appeared in different movie genres at some point. Here are some seriously underrated movies featuring big names.

1. Punch Drunk Love (2002)

punch drunk love 1
Image Credit: Sony Pictures Releasing.

Punch Drunk Love stars Adam Sandler and is a surprisingly emotional and moving film from one of the kings of comedy. Other stars in it include Phili Seymour-Hoffman and Luis Guzman. Sandler's character is violent and angry, but he finds love that turns his world upside down.

2. Forces of Nature (1999)

Forces of Nature Sandra Bullock, Ben Affleck
Image Credit: DreamWorks Pictures.

Forces of Nature is a somewhat whimsical movie about how love and nature work together. It features the lovely Sandra Bullock and the enigmatic Ben Affleck, who seem to collide into one another's lives and change everything. Their chemistry is apparent, and the plot is unique.

3. Fools Rush In (1997)

Fools Rush In Salma Hayek, Matthew Perry, Eddie Powers
Image Credit: Columbia Pictures.

Matthew Perry and Salma Kayek are mesmerizingly adorable in this highly underrated rom-com. Following a one-night stand, Hayek's character becomes pregnant, and the two must figure out what to do. The plot is simple, but the performances are sensational.

4. Six Days Seven Nights (1998)

Six Days Seven Nights Harrison Ford, Anne Heche
Image Credit: Buena Vista Pictures Distribution.

This film includes big names like Harrison Ford, David Schwimmer, and Danny Trejo, among others. The story follows the classic plots of haters to lovers, as two characters become stranded on a deserted island and must depend on one another.

5. Employee of the Month (2006)

Employee of the Month Jessica Simpson
Image Credit: Lionsgate Films.

Dane Cook and Jessica Simpson are a surprisingly cute couple in this workplace comedy. Cook's lazy, apathetic character becomes enthralled with the new employee at his job, played by Simpson. Cook and Simpson offer amazing comedic timing in this flick, along with Dax Shepard's in-your-face comedy.

6. Set It Up (2018)

Set it Up
Image Credit: Netflix.

This quirky film follows two tired assistants who want to get their bosses off their backs, so they set them up on a date! Big stars like Lucy Liu, Taye Diggs, Zoey Deutch, and Glen Powell make this movie better than anyone anticipated.

7. Drinking Buddies (2013)

Drinking Buddies Anna Kendrick, Ron Livingston
Image Credit: Magnolia Pictures.

Olivia Wilde, Anna Kendrick, Jason Sudeikis, Ron Livingston, and Jake Johnson all appear in this laidback romcom. Wilde and Johnson play coworkers with an obvious attraction toward each other, and the will-they-or-won't-they vibe and wry humor are persistent throughout the film.

8. Palm Springs (2020)

Palm Springs Tyler Hoechlin, Tongayi Chirisa, Conner O'Malley
Image Credit: Hulu.

Palm Springs is an eccentric and criminally underrated adventure romcom starring Andy Samberg and Cristin Milioti, as well as JK Simmons. The entire movie takes place on one wedding weekend, but some of the characters are stuck in a time loop where they relieve this dreadful day over and over again.

9. Safety Not Guaranteed (2012)

Safety Not Guaranteed Aubrey Plaza
Image Credit: FilmDistrict.

Aubrey Plaza, Mark Duplass, and Jake Johnson star in this indie movie. Duplass' character is planning to time travel and needs a partner when Plaza's very bored character volunteers. It's a feel-good comedy with all the charm and wit of a classic indie romance.

10. Definitely, Maybe (2008)

Definitely, Maybe Ryan Reynolds, Abigail Breslin
Image Credit: Universal Pictures.

While Definitely, Maybe is relatively well-known, it does not get the praise it deserves! This movie stars many big names, including Isla Fisher, Ryan Reynolds, Abigail Breslin, Rachel Weisz, and Elizabeth Banks. A father tells his daughter his life's love story, revealing a tumultuous ride that hasn't quite had a happy ending.

11. Leap Year (2010)

Leap Year Amy Adams, Matthew Goode
Image Credit: Universal Pictures and Optimum Releasing.

Leap Year is an endearing film with Matthew Goodie, Adam Scott, Amy Adams, Kaitlin Olson, and John Lithgow. Adams plays a woman determined to get engaged to her boyfriend. To make it happen, she takes a trip to Ireland to propose on Leap Day, and the journey isn't quite what she expected.

12. Lovebirds (2020)

The Lovebirds Kumail Nanjiani, Issa Rae
Image Credit: Netflix.

This adorable romcom stars Issa Rae, Kumail Nanjiani, and Anna Camp. It tells the story of a long-term couple who break up mutually but are forced to work together after they witness a murder. It's a hilarious movie that hits all the right comedic notes but is still heartfelt and romantic.

13. While You Were Sleeping (1995)

While You Were Sleeping Sandra Bullock, Bill Pullman
Image Credit: Buena Vista Pictures Distribution, Inc.

I grew up watching this and think it's one of the most romantic movies of all time. The cast includes Sandra Bullock, Bill Pullman, Peter Gallagher, Peter Boyle, and other big names. It's a quirky story about a comical misunderstanding and how love can be unexpected.

14. The Heartbreak Kid (2007)

The Heartbreak Kid Ben Stiller, Malin Akerman
Image Credit: Paramount Pictures.

Ben Stiller, Malin Akerman, Michelle Monaghan, Rob Corddry, and more stars appear in this sad but hilarious flick. The story follows Stiller's character after he rushes into a marriage with a woman who turns out to be awful, and he falls in love with someone else on the honeymoon.

15. Always Be My Maybe (2019)

Always Be My Maybe Keanu Reeves, Ali Wong
Image Credit: Netflix.

I don't understand why this movie isn't more popular because it's funny, emotional, and sad all at the same time. It stars Ali Wong and Randall Park, with appearances from Keanu Reeves. In the film, childhood sweethearts reconnect as adults and find there is still a spark.

Author: Veronica Booth

Title: Freelance Writer

Expertise: Food, Entertainment, Movies, TV, Fashion, Lifestyle, Celebrity


Veronica is a food, fashion, and entertainment writer from Boston, MA, with a passion for all things lifestyle and culture. She graduated from Boston University in 2019 with a bachelor's in English literature. From Anna Wintour to Angelina Jolie to Alton Brown, she has her finger on the pulse of all things Hollywood and celebrity.

If she's not in the kitchen crafting new recipes, then she's binging the latest HBO series and catching up on the hottest trends in Vogue.

She has written for and been syndicated by publications like The Weather Channel, The Daily Meal, The Borgen Project, The Good Men Project, The Express, MSN, Wealth of Geeks, and Not Deer Magazine. Her writing experience ranges from global news articles to celebrity gossip pieces to movie reviews to homemade recipes and more.