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Whether you have Valentine’s Day plans or not, snuggling up to watch a rom-com on Amazon Prime Video is always a fun way to spend an evening. The streaming network has everything you need to laugh, cry and yell at the hapless romantic hijinks that happen in these movies — sometimes the situations are all too absurd while other times, we can relate all too well.
Amazon Prime Video is releasing a fresh, romantic comedy just in time for cupid’s holiday. I Want You Back, starring Jenny Slate and Charlie Day, is an irreverent comedy about two strangers nursing their wounds after a breakup and deciding to ruin their exes’ new relationships. Day has some pretty good advice about why this is a very bad idea for anyone to do in real life. “You have to get right with yourself before you can get right with others,” he told the New York Daily News. “What’s great in this film is that the characters, they really have to come to terms with who they are as people and their behavior, and realize that they need to start taking care of themselves.”
So let the movie be a lesson in what not to do, but there are a few films out there that might give you tips on making a few romantic moves — try out a classic like Charade or a feel-good flick like Sleepless in Seattle. If you’re a true rom-com scholar, there’s a perfect new book out as a reading companion to your V-Day binge: From Hollywood With Love: The Rise and Fall (And Rise Again) of the Romantic Comedy by Scott Meslow, about the genre’s rich Hollywood history.
There are a ton of movies from the past that still hold up well and remind us that the rom-com never dies — it only inspires our sappy, little hearts even more.
‘I Want You Back’
Jenny Slate and Charlie Day star in Amazon Prime’s latest original movie, I Want You Back — out on Feb. 11. It’s a revenge rom-com about two strangers who bond over the end of their respective relationships and decide to try and win back their exes by ruining their new romances, which is never a good idea.
‘The Big Sick’
The Big Sick follows Kumail Nanjiani’s real-life journey of falling in love with his wife, Emily V. Gordon — which takes an unexpected turn when she falls ill. Zoe Kazan steps in for his wife in the movie, but the hilarious scenes also address the cultural differences between their families while the crisis is happening. Nanjiani and Gordon were also nominated for an Oscar for Best Original Screenplay because the movie is that good.
‘Sleepless In Seattle’
Who doesn’t get weepy over the magical pairing of Meg Ryan and Tom Hanks? A young boy calls into a talk radio show to help his dad find a new partner. A Baltimore reporter falls in love with his sad story of losing his wife and writes him a letter hoping he will show up to meet her on Valentine’s Day at the top of the Empire State Building. Will he show up?
When you have Queen Latifah and Common starring in a film together, you know it’s going to be a winner. She plays a physical therapist helping an NBA player rehab his injury while falling in love with him at the same time. He’s too busy trying to woo her childhood friend who doesn’t have the best intentions — it’s a classic love triangle.
If you haven’t seen 2007’s Waitress, what are you waiting for? Keri Russell plays a pregnant woman trapped in an abusive marriage in a very small town. She thinks her only way out is by winning a pie-baking contest — that is until she meets the married gynecologist in town, which only complicates her plans even further.
‘My Bossy Girl’
This South Korean rom-com is a classic story of how the geek gets the girl. Hwi-So is an engineering student, who is a member of the robotics club and his whole world is turned upside down when he meets the confident and outspoken Hye-Jin. This unlikely pair falls in love in the most awkward, but sweet way.
‘Love & Friendship’
This 2016 film based on Jane Austen’s novel, Lady Susan, is a delightful period comedy with Kate Beckinsale and Chloe Sevigny. Beckinsale plays a young widow, who rides out the rumors floating around about her dalliances at her in-laws’ estate. While there, she romances several suitors, which leads to quite a few mishaps.
‘Our Family Wedding’
An engagement gets a bit competitive, but not between the bride and the groom. It’s their fathers who work up a fuss and almost ruin the couple’s big day. A can’t-miss Valentine’s Day film with the adorable America Ferrara and the charming Lance Gross.
This 1963 classic with Cary Grant and Audrey Hepburn really has it all — romance, comedy, a murder mystery and the city of Paris. It has the feeling of an Alfred Hitchcock film and the charm of old-school movie stars, who really leaned into the glamour of that era.
‘But I’m A Cheerleader’
This satirical LGBTQ story starring Natasha Lyonne follows a popular cheerleader who is sent to a conversion camp after her religious parents believe she’s a lesbian since she loves Melissa Etheridge music and is a vegetarian. It’s a black comedy, but the 1999 movie was way ahead of Hollywood in tackling gay love stories with a lot of heart.
We already know that Julia Roberts and Richard Gere have romantic chemistry from Pretty Woman, so they tried it all over again in 1999’s Runaway Bride. It’s a simple premise — a reporter is assigned to a story to cover a woman who keeps on leaving her fiancés at the altar. Guess what happens next?
‘500 Days of Summer’
500 Days of Summer follows a nonlinear timeline, so be prepared for that, but once you dive into this heartfelt and sweet love story — you will be hooked. Joseph Gordon-Levitt and Zoey Deschanel give a realistic view of how frustrating and wonderful falling in love can be. And that dance scene to Hall & Oates’ song, “You Make My Dreams” will have you moving and grooving.
‘Something’s Gotta Give’
How did Diane Keaton get so lucky to have to choose between Keanu Reeves and Jack Nicholson? This 2003 film is sharply written and gives a wonderful spotlight for finding love after the age of 50 (your sex life is not over). Keaton also wound up with an Oscar nomination for Best Actress, so make sure to add this to your queue.
‘Boy Meets Girl’
There isn’t enough representation when it comes to transgender love stories, but this 2014 movie does a great job of delivering comedy and romance at the same time. A transgender woman in Kentucky has dreams of living in New York City to become a fashion designer, but an unexpected female friendship turns into a romantic one.
We know there’s a charming 2018 remake of Overboard with Anna Faris, but hear us out — the 1987 version is even better. Goldie Hawn and Kurt Russell’s on-screen chemistry is just as adorable as it is off-screen. Hawn plays a woman, who convinces her rich boss that he’s her blue-collar husband after he gets amnesia falling off a yacht, seems absurd, but that’s what makes this zany rom-com work.
This 2005 rom-com was loosely based off the 1967 film Guess Who’s Coming to Dinner?, but with the twist of a Black woman engaged a white man. Bernie Mac plays the father-in-law to be who gives Ashton Kutcher a hard time. But we are here for Zoe Saldana, who is delightful in the role of a daughter caught between her dad and her fiancé’s bickering.
If you want a Valentine’s Day with a little edge to it, then 1989’s Heathers is the perfect choice. Christian Slater and Winona Ryder are the Gen X antiheroes in the black comedy. The Heathers are the most popular clique in school until one loner teams up with one of girls to knock off each member by making it look like suicide. One of the most famous quotes from this cult film? “My teen angst has a body count.” Don’t miss it.
‘Love & Other Drugs’
This 2010 unconventional love story has Anne Hathaway and Jake Gyllenhaal enjoying a friends-with-benefits situation. Of course, that’s until they realize they are falling in love all while dealing with one of the character’s issues with early onset Parkinson’s disease. It doesn’t sound like a comedy, but we promise there are plenty of light moments in the film.
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