25 Best Indie Romantic Comedy Movies Of the Century

Romantic Comedy Movies - RubySparks

The Romantic-Comedy genre has served cheeseballs to audiences who have often flocked to them for a pat on the back for years. It has not only provided the audience with the much-needed hope that love is around the corner, but has also entertained them with neatly packed humor that makes a dolly out of life’s most lovable moments. However, with changing times the genre has undergone a makeover of sorts. More films have established the idea of a rom-com but have twisted the narrative to serve the greater good. Subverting the genre has thus become a common trait. Indie films of late have often done wonders within the genre itself.  The best romantic comedy movies of the decade have thus come out from the indie cinema. 20 of those are as follows:

25. Two Night Stand (2014) | Director: Max Nichols

Romantic Comedy Movies - Two Night Stand (2014)

While the writing is intermediately clumsy, Max Nichols’ “Two Night Stand” is benefited by charming performances by Miles Teller and Analeigh Tipton. After an online date, the two characters are stuck with each other due to a snowstorm. What follows is a funny, occasionally insightful look at modern-day relationships and the reason why some of them last, and some don’t.

Related to romantic comedy movies – Watch Two Night Stand on Netflix

24. Wristcutters: A Love Story (2007) | Director: Goran Dukić

Wristcutters_ A Love Story

Set in an afterlife, limbo-like space that looks exactly like our world, “Wristcutters: A Love Story” is about a place inhabited by people who kill themselves. Without a lack of emotion in the standard space, romance and friendship bloom in this darkly comic tale about connection.

Watch Wristcutters: A Love Story on Pluto TV

23. The Big Sick (2017) | Director: Michael Showalter

Big Sick

Kumail Nanjiani and wife Gordon’s real-life story served for an absolute charmer. Edgy and loveable, “The Bick Sick” showed how a cross-culture love story could be a fun, engaging and thoughtful to say the least. Featuring a mostly bed-ridden work from Zoe Kazan, the film cleverly subverts the rom-com genre by staying true to what it believes.

Related to romantic comedy movies – Stream The Big Sick Full Movie On YouTube

22. Obvious Child (2014) | Director: Gillian Robespierre

Obvious Child

Subverting the rom-com troops like a boss and featuring a breakout performance by Jenny Slate, “Obvious Child” takes up the challenging premise of a stand-up comic in a bad phase in life and does something truly honest with it. Based on a short from 2008,  Gillian Robespierre’s feature-length film is about a stand-up comedian who chances on a one-night stand post break up only to end up pregnant.

Similar to Romantic Comedy Movies: 25 Feel-Good Movies And Where To Watch Them

21. What If (2014) | Dir: Michael Dowse

What if

“What If” amps the romantic comedy movies structure with an assured wit and oodles of charm. Featuring rib-cracking dialogues that drive the young generation’s idea of love as just a facile phase of bad relationships and brilliant chemistry between stars Daniel Radcliffe and Zoe Kazan. Also, not to forget the vile but extremely pulling nature of both Adam Driver & Mackenzie Davis who shine even in small roles making this film one of the best romantic comedy movies of the decade.

What If Full Movie Streaming On Youtube | What If Movie Netflix

20. About Time (2013) | Director: Richard Curtis

About Time (2013)

As far as romantic movies are concerned, Richard Curtis sure knows how to paddle your heartstrings and make you feel sappy. But as long as time travel movies are considered, “About Time” manages to sincerely tread the lines of sentimentality with a poignant study of love and the need to cherish it forever.

Related to Romantic Comedy Movies  – Watch About Time on Netflix

19. Much Ado About Nothing (2012) | Director: Joss Whedon

much Ado About Nothing (2012)

Know for directing a couple of Avengers films before retreating from the genre, Joss Whedon’s funny spin on Shakespeare’s classic comedy is both smart, funny and truly absurd. Shot in beautiful black and white, “Much Ado About Nothing” uses the original text to formulate a euphoric experience that is filled with post-modern absurdity.

18. Celeste and Jesse Forever (2012) | Director: Lee Toland Krieger

Romantic Comedy Movies - Celeste and Jesse Forever (2012)

Featuring a star-making turn from Rashida Jones, “Celeste and Jesse Forever” twists the we-are-still-friends-after-a relationship genre. The film is full of likable yet deeply flawed and vulnerable characters who fall into the trap of understanding their life and how a relationship eventually fall apart or stay true. In doing so, it becomes a truly wise investigation of modern-day love.

17. 2 Days In Paris (2007) | Director: Julie Delpy

2 Days In Paris (2007)

Also serving as a proxy spot for the 2012 sequel named 2 Days in New York (2012); starring Chris Rock, Julie Delpy’s duology about the insecurities and hyperboles of romantic relationships, 2 Days in Paris follows a couple that takes a pit stop at the girl’s parents only to learn more about one another. Funny, full of charming moments and keenly observed moments about how relations grow and stay together, Julie Delpy’s debut feature should be watched to witness just how talented the woman is.

Watch 2 Days in Paris on TUBI TV

16. Drinking Buddies (2013) | Director: Joe Swanberg

Romantic Comedy Movies - Drinking Buddies (2013)

Joe Swanberg’s observational rom-com has a deep understanding of slackers who are unwittingly unable to understand what they really want in their lives. Featuring brilliant performances across the board – Especially by Olivia Wilder and Jake Johnson; “Drinking Buddies” is one of those films where nothing much happens but it leaves you with an aftertaste that is almost equivalent to waking up to a night of home-brewed beer.

15. Enough Said (2013) | Director: Nicole Holofcener

Romantic Comedy Movies - Enough Said (2013)

Nicole Holofcener’s “Enough Said” is one of those grown-up romantic comedy movies that truly understand the characters it wants to talk about. It also wisely investigates how the very fabric of a relationship is questioned when we are constantly indulged in an environment that only spits venom. Featuring James Gandolfini’s very last performance Holofcener perfects captures the insecurities that abound people who otherwise have a very perfect and healthy being.

14. Easy A (2010) | Director: Will Gluck

Easy A (2010)

Gracefully owning up to its inspirations – vis-à-vis a direct homage to high school teenage comedies by John Hughes, “Easy A” is raunchy, hilarious and often intelligent romantic comedy that re-imagines the “The Scarlet Letter” in a modern-day American school. Featuring a sassy and spunky performance by Emma Stone, the film’s outlook towards rom-com gives it a completely original voice.

Watch Easy A on Netflix

13. Liberal Arts (2012) | Director: Josh Radnor

Romantic Comedy Movies - Liberal Arts (2012)

One thing’s for sure, Josh Radnor has insights way beyond his still young years. In only his second outing he shows why college and the life that one has gone past is so addictive. It also showcases a kind of romance that is both insightful and unpredictable. Which makes “Liberal Arts” a wise and enjoyable study of growing to accept one’s contentment.

12. Don Jon (2013) | Dir: Joseph Gordon-Levitt

Don Jon (2013)

“Don Jon” is not just Joseph Gordon-Levitt’s first attempt at going behind the camera, but it’s also a smart, sexy and ultimately intelligent spin on the romantic-comedy movies. Grounding itself in a fantasy-filled life of a porn-addicts life post work and relationships, this witty retelling of the rom-com subverts expectations when it also becomes an honest, heartfelt investigation of what changes, makes and breaks relationships in the modern world.

Related to Romantic Comedy Movies – Watch Don Jon On Netflix | Also, Watch Don Jon Full Movie Online on YouTube

11. Your Sister’s Sister (2011) | Director: Lynn Shelton

Romantic Comedy Movies - Your Sister's Sister (2011)

Lynn Shelton’s “Your Sister’s Sister” is one of those films that takes you by surprise as to how simple yet complex they could be. With a trio of perfect performances, this little fable believes in its spontaneity and becomes a funny charmer that investigates criss-cross relationships with genuine warmth.

9. Safety Not Guaranteed (2012) | Director: Colin Trevorrow

Safety Not Guaranteed (2012)

While not sold-proof to be called a romance in the traditional sense, this oddball sci-fi comedy is more endearing and heartful than most manipulative romances. Focusing on the genuine chemistry between the people, “Safety Not Guaranteed” brings together the idea of lost dreams and missed chances in a roundabout that only warms your heart up.

8. The One I Love (2014) | Director: Charlie McDowell

The One I Love (2014)

An eerie, creepy, and occasionally surprising entry to the romantic comedy movies genre, the less you know about Charlie McDowell’s “The One I Love” the better. Smart, subversive, and rhetorical when raising essential questions about idealizing and questioning relationships, this Elizabeth Moss and Mark Duplass film should be watched – Both by thriller and relationships comedy enthusiasts.

7. Sing Street (2016) | Director: John Carney

Romantic Comedy Movies - Sing Street (2016)

John Carney’s “Sing Street” is like a hip pop-song that you wish never ended. An optimistic, innocent and energetic musical drama that charms your pants off with its exhilarating series of characters and vibrant, realistic emotions. The reason why the romance in Sing Street feels relatable can never be pinpointed but since it knows how to differentiate between happy-sad and sad-sad everything is forgiven.

Related to Romantic Comedy Movies – SING STREET [2016]: FRACTURED LIVES AND BROKEN DREAMS

6. 500 days of summer (2009) | Director: Marc Webb

500 Days of Summer

Marc Webb’s clever and offbeat romantic-comedy understands what most Hollywood counterparts so gullible. Relationships are often messy and things don’t pan out the way one wants,  “500 Days Of Summer” gives both an oral and visually honest portrayal of a relationship that is bound together by a glue that harkens back to Woody Allen’s classic rom-com “Annie Hall.”

Stream 500 Days of Summer Full Movie on YouTube

5. Ruby Sparks (2012) | Director: Valerie Faris, Jonathan Dayton

Romantic Comedy Movies - RubySparks

Witty, charming and smartly written, “Ruby Sparks” is the rare romantic comedy that re-evaluates the manic pixie dream girl while also being a metaphor about understanding the real essence of love. Performed wonderfully by a promising Paul Dano and Zoe Kazan, this is one of those romantic stories that rightfully enjoys its bizarre premise to brings something truly interesting to the foreground.

4. Comet (2014) | Director: Sam Esmail

Comet (2014)

Truly divisive and filled with cynical and abrasive characters, Sam Esmail’s “Comet” is a sensory experience like no other. Sprawling through multiple dimensions where the two people explore their contentments, life choices and other essential decisions, the film contemplated why love is often not what it seems to either of the two people in question.

Buy Comet movie online on Amazon

3. Me and You and Everyone We Know (2005) | Director: Miranda July

Me and You and Everyone We Know

Slated as one of the earliest films that truly understood how we as people will interactive over the internet, Miranda July’s erratic and uncomfortable humor really delved into the human need for intimacy and being loved. Seen through an uncanny eye for human behavior and a kind of hopeful maturity that still revels in innocence, Me and You and Everyone We Know is a suburban comedy that can win your heart over if you let it.

Stream Me and You and Everyone We Know on Criterion Channel

2. Submarine (2010) | Director: Richard Ayoade

Submarine (2010)

While essentially a coming of age story; Richard Ayoade’s stylish first feature is a super-funny comedy about adolescence and the romance that feels like the end of the road to the growing brain. “Submarine” investigates both the inner and outer turmoil of a confused boy’s love life.

1. Her (2013) | Director: Spike Jonze

Her (2013)

In Spike Jonze’s fourth feature film, a guy falls in love with his operating system and somehow it seems beautiful and entirely believable. Featuring a wonderfully bizarre premise, some breathtaking sequences and a heartbreaking story that idealizes futuristic love in a contemporary setting, “Her” becomes one of the best romantic comedies ever made.


Shikhar Verma

Getting fat with the wife. Absolutely loves the all-consuming, indulgent world of cinema.