When Harry Met Sally, Groundhog Day, & The Wedding Singer.

15 Funny Romantic Comedies To Watch This Valentine's Day

When Harry Met Sally, Groundhog Day, & The Wedding Singer.
When Harry Met Sally, Groundhog Day, & The Wedding Singer. Courtesy of Columbia Pictures & New Line Cinema.

Valentine’s Day is around the corner and with that in mind, you’re probably planning what you wanna do for you & your partner on February 14th (or perhaps any date night for that matter). If you’re looking to spend the night in for a low-key movie night and need some solid & funny rom-com recommendations, 800 Pound Gorilla News has got you covered.

The writing staff got together to select our picks for the funniest & best romantic comedies to watch this Valentine’s Day. This year’s list has something for everyone and spans many decades from classics like When Harry Met Sally to newer favorites like Set It Up.

We hope one of these films brings you lots of laughter & heart like they have for us - please enjoy!

If you purchase an independently reviewed product or service through a link on our website, 800 Pound Gorilla News may receive an affiliate commission.

Forgetting Sarah Marshall

Getting over an ex is never an easy thing to go through. And it definitely didn’t get easier for Peter (Jason Segel) when he decides to go on a road to recovery by taking a lavish trip to Hawaii and somehow manages to run into his ex (Kristen Bell) shortly after breaking up and see she’s already moved on with a British rockstar, Aldous Snow (Russell Brand). As Peter figures out how to move on, he starts to form a new fling with the hotel concierge Rachel (Mila Kunis), who starts to bring out the best in him through their crazy adventures across the island.

This cast combined with Segel's writing & Judd Apatow producing just shortly after making The 40 Year Old Virgin & Knocked Up hands down make Forgetting Sarah Marshall one of the essential romantic comedies for all comedy fans. This movie’s filled with just as many classic quotes & hilarious moments as there truly is heart & its feel good moments. Not to mention, one of the best things to come out of this movie was its just as funny (if not, possibly funnier) spinoff with Aldous Snow & Aaron Green (Jonah Hill, who actually plays Matthew in this movie) leading a new adventure in Get Him To The Greek.

How to watch: available for rent & download on Prime Video!

Anyone But You

It seems like it's been a long, long time since we’ve gotten a proper romantic comedy with the theatrical treatment compared to the usual streaming treatment we see nowadays. For the last four decades or so, there’ve been so many romantic comedies we now call classics that hit the theater consistently year after year and it seems like we haven’t gotten as many since the early 2010’s. There have been a few notable ones in between then & now including Crazy Rich Asians & Kumail Nanjiani's The Big Sick to name a few. But perhaps that’ll change after seeing the box office sleeper hit, Anyone But You, ring in a new era of rom-coms with its unexpected & surprising $152+ million worldwide draw on its $25 million budget. And we can confirm, it’s downright hilarious, sweet & full of heart.

This modern take on William Shakespeare’s Much Ado About Nothing stars Hollywood eye candy Sydney Sweeney & Glen Powell as the leading couple, Bea & Ben, who only appear to be perfect, when in reality, they actually hate each other's guts after a faulty incident post-first date. Yet, they reunite again when they’re unexpectedly thrust together at the same destination wedding along with each other’s exes. Which leads them to pretend to be a couple with the hopes of winning each other’s exes over again. But do they ever actually fall in love with each other? We’ll let you experience that for yourself.

Admittedly, this movie doesn’t belong on a classic rom-com movies list (yet, maybe give it a couple years). However, don’t let that stop you from enjoying this fun date night film. Powell & Sweeney have great chemistry with each other & surprisingly good comedic chops. If you have any emotional attachment to Natasha Bedingfield’s grand slam smash Unwritten, you’ll appreciate this movie a lot in the way it’s used!

How to watch: it’s still in theaters with its well deserved Valentine encore!

Friends With Benefits

In 2011, Mila Kunis & Justin Timberlake were in the middle of riding their big acting waves experiencing massive success following each of their respective films Black Swan & The Social Network, both very dramatic-leaning films. So what do they both do after reaching that Oscar buzz high? They lighten up & star together in this easy-watch, enjoyable, charming & at times pretty funny to the books rom-com: Friends With Benefits.

From seasoned director Will Gluck (the Easy A director who would eventually go on to direct Anyone But You), comes a movie surrounding two recently single late twenty somethings, Jamie & Dylan, who each have their own sets of emotional baggage and become friends as Dylan accepts a new job working at GQ in New York. Once they start to find out how much they have in common with each other, their mutual attraction grows & they decide to have some deep fun without all the emotional baggage (we’ll let you infer what the “deep fun” is here). This movie is very playful and without a doubt knows how much fourth wall it breaks pointing out Hollywood cliches and bringing out all the stops to make this a feel-good rom-com; some of these including flash mobs, pointing out rom-com movie qualities within its own movie, the whole exploring New York vibe and more. Nothing new is added here to the genre, the movie’s clear strength here is the undeniable on-screen chemistry Kunis & Timberlake have with each other. And there are some solid funny moments throughout. Emma Stone, Andy Samberg & Woody Harrelson also have some funny moments here too. If you’re looking for a fun throwback movie, this might be the one to either revisit or watch for the first time.

How to watch: streaming on Paramount+!

The Wedding Singer

Adam Sandler absolutely ruled in the 90s with his meteoric rise as a comedian, actor & performer. He set a new precedent for comedy film making & characters with his first big films Billy Madison & Happy Gilmore. Those films paved the way for The Wedding Singer, his first starring role in a truly classic romantic comedy that continues to be revisited to this day since its release in 1998. This story revolves around wedding singer Robbie Hart (Sandler) who gets left at the altar at his own wedding and gets stuck with a broken heart doing one of the most romantic jobs in the world. But then comes Julia (Drew Barrymore), who enlists the singer to help plan her wedding where they start a mutual connection with each other. Hart falls for Julia and it’s up to him to win her over before that wedding arrives.

His performance in this movie alongside co-star Drew Barrymore was so loved & adored that they co-starred in two more rom-coms together, 50 First Dates (2004) & Blended (2014), where the two continue to display their infectious chemistry (here’s to hoping we might get a fourth movie). Comedy fans who haven’t seen this movie yet will absolutely appreciate all the greats involved including stellar writing from Tim Herlihy (Billy Madison, Happy Gilmore, The Waterboy and more) and classic cameos from Jon Lovitz, Steve Buscemi, Kevin Nealon and of course, who can forget Billy Idol.

How to watch: available for rent & download on Prime Video!

Cha Cha Real Smooth

Let it be known here: Cooper Raiff is a talent & force to be reckoned with. He not only stars, he also writes & directs this truly brilliant film that makes you feel like you’re experiencing a warm hug & a gut punch all at the same time. You may be familiar with his 2020 debut starring, writing & directing offering Shithouse that got a ton of critical acclaim and brought him here to his latest film.

Cha Cha Real Smooth is a solid coming of age story that does fit for the most part into the romantic comedy genre (with a good hint of dramedy throughout). This story follows Andrew (Raiff) who moves back to his hometown after graduating from college and tries to get back on his feet with a clear path forward. That path starts to become clearer once he discovers he has a natural gift as a party starter & for getting kids & parents moving on the dance floor via his younger brother’s classmates bat mitzvahs. It’s at one of these bat mitzvahs he befriends a mom (Dakota Johnson) and her autistic child and he starts to form a unique bond and close relationship. From there, he begins to discover the path he wants to pursue beyond living at his parents’ house.

This movie may not be your traditional rom-com even though it doesn’t even completely fit that mold. However, if you’re looking for something different that has the romantic charm, is truly funny, and doesn’t follow the run of the mill rom-com formula (perhaps fresh), you may really like this movie. It’s a true delight and one worth checking out!

How to watch: streaming on Apple TV+!

Plus One

Maya Erskine rules in this film as a vulnerable-but-unsure person navigating what she wants out of life in connection to the relationship modeled for her by her parents. Jack Quaid rules as a charming solid dude who likes Erskine. The film is genuinely funny and relaxed, to the point where it feels like this deserved a bigger theatrical push when it came out. Not everything here works, but there’s such incredible talent here that it doesn’t matter. If anything, the film works as a sort of barometer for what Erskine can do, which is anything.

Erskine is a unique performer that has so few points of comparison, except for maybe Jessica Williams or Donald Glover. Everyone she plays feels more than the role required, which puts her in a category of someone who always deserves better, for the most part. In her friend and occasional collaborator, Anna Konkle, is a steady and timing-based performer, Erskine is more akin to an outlier like Prince or Jesse Plemons, someone who has those same instincts, but gets at the thing in such a deep way that the edges are smoothed out, and the finesse required blends seamlessly with the nuance of what they envision. If you consider Wine Country, or Pen15, it always feels like Erskine is who she is pretending to be. The edges that let the light through the cracks of her acting aren’t visible, so it just feels like actors entered her world, not the other way around.

Here, that’s true in a way that just lets Erskine dunk and be charming and alluring while also building a character that feels sturdy and dynamic. Plus One is really for anyone, but if you’re watching Mr. & Mrs. Smith right now, and want to see more from someone who is giving Donald Glover a run for his money as co-lead, this is where to start.

How to watch: streaming on NetflixHulu!

Set It Up

Everyone knows Glen Powell now as a real beefcake boy, but in 2018, he was kind of a charming dorky comedic actor who was thin and tired-looking. Here, he stars opposite Zoey Deutch, who steals the show in a lot of ways, as two personal assistants trying to get a break from their bosses, so they decide to set them up. It is very hard to stand shoulder-to-shoulder with Lucy Liu and Taye Diggs, but Deutch does it effortlessly, while Powell dips in and out of being able to handle himself.

You may ask, why would I want to watch Glen Powell struggle? For one, it’s funny, but two, the film is funny. Genuinely, the film actually has jokes that hit, and isn’t just a film that has a bunch of bullshit set pieces or lazy lines that writers like me might be too tired to say anything bad about. It is so rare to get a good rom-com now, and even rarer to feel like everyone is committed to doing the best work they can. Liu and Diggs are operating at between 80 and 100% the entire time, but Powell and Deutch are giving it everything they’ve got. It doesn’t matter if Deutch laps Powell, because they’re good collaborators and great scene partners.

If you want something less romantic, but funnier than you’d ever expect, Set It Up is the one to pick.

How to watch: streaming on Netflix!

The Weekend

Sasheer Zamata put out a great special with us last year, but the fact of the matter is that Zamata has been overlooked and counted out in odd ways her entire career. On Saturday Night Live, the show seemed indifferent to her genuine brilliance and hilarious cunning, even if she handled the limitations of the show with grace. In her acting career, there’s so much more Zamata can be given to do, if anyone is willing to take a chance. This film makes a great case for her as a romantic charmer, equally adept at playing and matching chemistry as she is being skeptical and unsure about her comfort with vulnerability.

The Weekend is a delightful romantic comedy in a new-yet-old-fashioned way. The film is very clean and precise in the way it moves, but doesn’t sacrifice any of the comedy beats or heat between Zamata and Tone Bell, another actor who has always deserved more. The film came out in 2018, and while both comics deserve bigger and more interesting opportunities, at least here they fill up the screen with wattage that is unmatched, or perhaps matches what casting directors put in front of us over and over again.

If you want something that feels unmessy, and is more in-line with romantic comedies of the 70s and 80s, this is for you. If you’re looking for something that gives two genius Black comic actors the chance to really burn the set up, this is definitely for you.

How to watch: streaming on Max!

Love Jones

Nia Long, the most underrated true star to maybe ever work in Hollywood, finally, finally got her due in this romantic film that is as close to an American In the Mood for Love as we’ll get, since it’s crossed with the spirit of films like The Best Man. IS the movie funny? In a clever way, yes. However, the film is on this list because it’s simply perfect, evoking the feeling of an epic love story while also feeling like it's capturing Black intellectualism and artistry as it was shaping the 90s and 00s in beautiful and profound ways. It’s the only American film I’ve ever seen that feels like music and poetry, which are important to the plot’s heartbeat.

Love Jones is classy in a way films tend not to be, but doesn’t ever feel stuffy or languid. Instead, the film feels timeless, as true about relationships, monogamy, and the value of art to connecting with someone as ever. The slow and genuinely sensual love that wins out between Lorenz Tate and Nia Long is impossible to not feel thrilled by, and the supporting cast are all equally centered in their own lives, not just second to the leads, but genuine people. In Nia Long’s Nina Mosley, Theodore Witcher gives us a defining 90s crush, not because Long is simply beautiful (she is, and then some), but because she has a life before Tate’s Darius Lovehall comes into it, and the film hinges on his being able to fit with her ambitions, rather than her pining for a man as the world spins forward.

How to watch: streaming on Paramount+!

The Incredible Jessica James

Jessica Williams is having some recognition with Shrinking and Love Life, but it’s not enough when you consider how good she was in this film from 2017. The film has assists from Chris O’Dowd and LaKeith Stanfield, but the film loses its breath when Williams is on screen, since she is not only charismatic and funny and sexy, but just magnetic. This vehicle is the rare time where the “it” factor becomes so clearly understandable, and even in sillier moments, the film can’t diminish or otherwise make Williams sweat her performance.

Here’s what’s wild about The Incredible Jessica James: it’s a rare thing where you’re watching someone both inhabit a character while still being themselves on screen. It’s like watching Williams be on 2 Dope Queens while also being on Shrinking. Really, all of her performances are as cool and perfect as this one, but this is the one that feels overlooked, no matter how much success she’s having.

Normal people: watch this if you’re looking for a cool, sexy, funny hang that feels like the start of something beautiful. Powerful, Hollywood types: Watch this and give Williams more big roles!

How to watch: streaming on Netflix!

High Fidelity

In 1995, Nick Hornby set out to write his debut novel. Set in London, the story follows Rob, who has to come to terms with his relationship with Laura falling apart. This causes him to revisit his exes and re-examine his dating history. The story is relatable to any music obsessive or pop culture junkie, given that it’s set in the record store that Rob owns. The book was so successful when it came out that it was optioned pretty much right away.

A few years later, the film was set in motion at Touchstone, with John Cusack starring and Stephen Frear directing. Cusack, DV DeVincentis, and Steve Pink opted to move the story from London to their native Chicago, to help invoke their own experiences into the film. While that is a gamble for most adaptations, they were determined to remain very dedicated to the source material. It also features a breakout performance from Jack Black, who plays Barry, who works in Rob’s record store.

High Fidelity has managed to achieve a cult classic status in the years since it first came out. It’s not only one of the best music-based movies ever made, but it’s also - at its core - a love story. We see a complicated character trying to grow up and figure out what’s next in his life.

How to watch: available for rent & download on Prime Video!

Coming To America

Coming To America is your classic Cinderella story. And it’s based on real life, sort of. In the 1980’s, Eddie Murphy had a tough time distinguishing if a woman loved him for him or if because he was a wealthy movie star. So Coming To America follows Akeem (Murphy), an African prince who travels to New York where nobody knows he is rich to find his true love. Murphy enlisted his go-to writers from SNL - David Sheffield and Barry Blaustein - and went to his old friend John Landis to bring this fairy tale to life.

The film is a classic love story, while being updated for the-modern times. It’s one of Murphy’s greatest performances, and was one of the first where we got to see him playing more of a straight man against a truly crazier backdrop. As for the crazy backdrop, thanks to the film, we got to learn all about McDowel’s (the McDonald’s ripoff) and Soul Glow. That’s priceless. There’s a reason why so many people today hold this film in such high regard.

How to watch: available for rent & download on Prime Video!

Groundhog Day

The time loop genre has become a cinematic staple. But we guarantee you that for every modern time loop film, the thing they’re trying to escape most is Groundhog Day. That’s because Groundhog Day is regarded as one of those perfect films where everything managed to go just right. It was so successful that saying something is “like Groundhog Day” is embedded in our pop culture.

The film stars Bill Murray as an arrogant, self-centered weatherman named Phil who is assigned to go cover the Groundhog Day festivities in Punxsutawney, something he detests doing every year. When a huge blizzard keeps them stranded there over night with his producer Rita, Phil wakes up to discover he’s living the same day over again. While Phil’s relationship with Rita is antagonistic at first, they start to share a bond as Phil gradually changes - slowly - over the course of the film, managing to fall in love. Of course, Phil does use the time loop to his advantage as a mechanism to try and win her over. At a certain point, it becomes less about trying to escape the endless time loop and about how to change within it.

The film is one of the rare ones that has continually stood the test of time upon each viewing. It marked the end of Harold Ramis’ collaboration with Murray, but it features both men at the top of their game. It works not just as a comedy, but as an experiment for just how long it would take someone like Phil to change their behavior, and start to welcome others into their lives.

How to watch: available for rent & download on Prime Video!

When Harry Met Sally

Without a doubt, a gold standard in the world of romantic comedies, Rob Reiner’s When Harry Met Sally is highly regarded as one of the best. The film came along in the midst of Reiner’s hot streak as a director, one that lasted for the 1980’s and the first half of the 1990’s. This film is at the center of that streak.

The film - which stars Billy Crystal and Meg Ryan - follows Harry and Sally who first meet on an 18-hour car ride from Chicago to New York post-graduating college. It’s not love at first sight, and the two go their separate ways after the trip. But gradually over time, they keep running into each other, and build a strong bond as friends. Over the course of that friendship, we watch them finally give into the temptation of falling in love, while answering the question whether having sex would ruin their friendship and get between them.

While the film follows a relationship that is hardly love at first sight, it has gone into become a staple of every Valentine’s Day. It is embedded in pop culture at this point. But perhaps no moment is more iconic than the line in the deli, “I’ll have what she’s having.”

How to watch: available for rent & download on Prime Video!

Chasing Amy

In 1997, Kevin Smith followed up his first two film’s by showing a more sentimental side with Chasing Amy. It couldn’t be farther from your standard romantic comedy, however. The film follows a comic book artist Holden (played by Ben Affleck), who falls in love with a fellow comic book artist Alyssa (played by Joey Lauren Adams) who reveals to Holden that she’s gay. A very smitten Holden eventually gets into a relationship with Alyssa, but soon realizes he’s uncomfortable with her past having been with men previously.

The movie says a lot about being in a committed relationship, and what we’re willing to accept from our significant other. It’s also just as much a bromance story between Holden and his creative partner, Banky (played by Jason Lee). The film manages to go beyond the easy comedic premise of a guy falling in love with a lesbian, and finds a whole lot of depth underneath that surface.

How to watch: streaming on Paramount+ & Prime Video!

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