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20 Best Romantic Comedies to Watch

How to Loose a Guy in 10 Days

#20. How to Lose a Guy in 10 Days

He takes up a challenge to make a woman fall for him. She wants a guy to play out the idea of her upcoming article “How to Lose a Guy in 10 Days”. What follows is a hilarious turn of events. Both Kate Hudson and Matthew McConaughey shine in this fine cocktail of comedy and romance.

Forgetting Sarah Marshall

#19. Forgetting Sarah Marshall

After his break-up with Sarah Marshall (Kristen Bell), Peter Bretter (Jason Segel) decides to go to Hawaii for a vacation. Soon he finds out that Sarah and her new boyfriend have checked in at the same resort as his. ‘Forgetting Sarah Marshall’ is a well-acted piece and thoroughly enjoyable.

Nick and Norah's Infinite Playlist

#18. Nick and Norah's Infinite Playlist

Nick, played by Michael Cera, is still obsessed with his ex-girlfriend, Tris. One night, Tris’ friend Norah (Kat Dennings) suddenly shows interest in him at a club. Thus begins a night full of ups and downs that are both awkward and hilarious. The movie is filled with sweet moments and a beautiful soundtrack. One of the most underrated feel-good rom-coms for sure.

What If

#17. What If

Wallace (Daniel Radcliffe) has had several failed relationships. Things start to change when he meets Chantry (Zoe Kazan). Soon they realise that they are falling for each other, the only problem – Chantry already has a boyfriend. The lead pair delivers with an adorable performance. An example of the magic of simple stories.

#16. Definitely, Maybe

Ryan Reynolds plays Will Hayes, a mid 30s father who is going through a divorce. One day her daughter, Maya, starts asking him about how he met her mother. Will starts recalling all the women in his life and finally realises his true love. ‘Definitely, Maybe’ keeps it simple yet sweet, and thus deserves a spot in the list.

#15. Crazy, stupid Love

Cal Weaver’s (Steve Carell) life was going great until one day he learns that his wife wants divorce. Now Cal, who is over 40, finds himself struggling in the world of dating. Enter Jacob Palmer (Ryan Gosling), a self-styled player who agrees to help Cal to be a hit with the ladies. Carell is hands down the best thing in this movie and shows why he is considered one of the best actors in comedy. Hilarious, heartfelt and rewatchable.

#14. Groundhog day

Phil Connors (Bill Murray) goes to the town of Punxsutawney as a weatherman to cover the groundhog day. Soon he realises that he is reliving the same day over and over again. Even though the plot may not seem interesting at first, Bill Murray’s honest portrayal of a guy falling in love and trying to be a better person eventually, will leave you with a smile.

#13. Pretty woman

A modern take on Cinderella, where a woman of the evening (Julia Roberts) and a handsome rich man (Richard Gere) eventually fall in love. It’s a predictable story, but the undeniable chemistry between the leads shine bright. A fairy tale film with a stellar cast and a brilliant soundtrack.

#12. Straight Up

Straight Up tells the story of two people, Todd (James Sweeney) and Rory (Katie Findlay). Todd is struggling with his sexuality, OCD and many other things. But when he meets Rory, they strike up a deep bond. This is the most unusual story told in the most adorable way and thus deserves all the praise.

#11. Enough Said

Eva (Julia Louis-Dreyfus), a divorced single parent, starts dating Albert (James Gandolfini). Soon she finds out that Albert is the ex-husband of her new friend Marianne. The movie doesn’t shy away from topics like mid-life crisis and insecurities of being a parent. If you are tired of the same old teenage rom-coms, ‘Enough Said’ might be the perfect movie for you.

#10. Obvious Child

Donna (Jenny Slate), a female comic, develops an instant liking for Max (Jake Lacy), after their one-night stand. But her world turns upside down when she finds out that she is pregnant with his child. ‘Obvious Child’ refuses to follow the usual. It’s subtle, sweet and criminally underrated.

#09. Plus One

Ben (Jack Quaid) and Alice (Maya Erskine) have been friends for a longtime. For the summer they decide to be each other’s plus one at all the weddings that they are invited to. ‘Plus one’ is smart, funny and fresh. An underrated gem to brighten your mood.

#08. Long Shot

Fred Flarsky (Seth Rogen) is a gifted journalist who somehow always gets into trouble. Charlotte Field (Charlize Theron) is one of the most influential women in the world, running for the presidency. When Fred unexpectedly comes across Charlotte, he realises that she was his former babysitter and childhood crush. ‘Long Shot’ is filled with hilarious one-liners and memorable dialogues. Maybe one of the best additions to this genre in recent times.

#07. Silver Linings Playbook

After losing his wife and job, Pat Solatano (Bradley Cooper) finds himself living with his parents. Soon Pat meets Tiffany (Jennifer Lawrence), who agrees to help him get back with his wife. ‘Silver Lining Playbook’ is both funny and heartbreaking in its story and deals with issues like mental illness, while still being loyal to its genre. Watch out for Robert De Niro showing off his comedic chops.

#06. Jerry Maguire

Jerry Maguire (Tom Cruise) is a sports agent who gets himself fired over his honest, heartfelt memo. Jerry starts his own management firm with single mother Dorothy Boyd (Renee Zellweger) and just one client in hand. Soon Jerry and Dorothy begin to fall in love while they struggle to make their business venture work. Tom Cruise steals the show as the agent trying his best to save both his professional and personal life. And yes, “you had me at hello” perfectly sums up this warm and beautiful rom-com.

#05. You’ve Got Mail

Struggling bookseller Kathleen Kelly (Meg Ryan) hates Joe Fox (Tom Hanks), the owner of a rival corporate book store. But when they meet online, unknowingly they begin an anonymous internet romance. ‘You’ve Got Mail’ is a classic enemies-to-lovers story with two of the most brilliant actors in the lead. Even after so many years the film remains fresh and relevant.

#04. The Big Sick

Kumail Nanjiani, a Pakistani comic, meets Emily (Zoe Kazan), a graduate student, at one of his small gigs. Soon the pair hit it off. But Kumail finds himself lying to his conservative Muslim family about Emily. ‘The Big Sick’ is all that is good in this genre. Add to this the fact that this is based on the real life romance of the comedian. It’s sweet, sad, funny and above all heartwarming. A soon to be rom-com classic.

#03. Annie Hall

Comedian Alvy Singer (Woody Allen) tells the story of his relationship with nightclub singer Annie Hall (Diane Keaton). While at it, Singer reflects on his childhood, adult years and all other past relationships. Allen breaks the fourth wall time and again, mostly highlighting all the shallow aspects of modern relationships. ‘Annie Hall’ is brutally honest and hysterically funny. The one with the wisest quotes.

#02. Notting hill

William Thacker (Hugh Grant) is a London bookstore owner who is happy with his dull, ordinary life. But when he accidentally meets and falls for the famous American actress Anna Scott (Julia Roberts), his world turns upside down. A movie with the best soundtrack, dialogues and a brilliant supporting cast. Hugh Grant’s effortless comic timing and Julia Roberts’ celebrity charms make this the ultimate rewatchable classic. ‘Notting Hill’ is your rom-com 101.

#01. When Harry met Sally

“Can men and women ever be friends?”. This quintessential romantic comedy tries to answer the question with the story of Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) who somehow end up being friends after knowing each other for almost 11 years. Over the years we see the growth of these characters and how their paths cross unexpectedly. The oh-so-adorable chemistry between the leads and the hilarious dialogues will keep you glued throughout. ‘When Harry met Sally’ is where all the clichés work best. The movie heavily influenced numerous future endeavours in this genre and that’s why many consider this as the greatest rom-com of all time.

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