We know: sometimes, romantic comedy movies can feel a little cheesy. Not everyone is so embracing of the inherent optimism that comes along with a good old romcom. But we have good news—not everything in the ever-so-wide-ranging world of romantic comedies is lovey-dovey mushy-gushy. Sure, that's the genre, so that stuff is always going to be in there somewhere. But it's one of the most loved and frequently-visited genres for a reason, and many of those people visiting are actually quite funny. That can include actors, writers, writers who act, actors who write, and everyone else involved in making something that might culminate in us laughing aloud if everything goes according to plan.
Sometimes, that means visits from people you'd think of as just, well, funny—that means Seth Rogen, Kristin Wiig, and Billy Crystal, for some. Other times, that means some of the best TV shows you may or may not have seen (HBO and Hulu come in handy there). And other times you'll find romcom laughs even in places you're not looking.
That's why we took the time to do the homework and wrap it all up for you. It can be tricky to search through all those streaming services just to find the movie that might feel right for the mood you're in right this second or maybe the mood you might be in next week. So, here's the guarantee: all the movies on this list have some of the semblances you're looking for. In one way or another, they're romantic comedies, but most importantly they've got the most important part: major laughs.
Knocked Up (2007)
Perhaps the most tender (and maybe also the funniest) of Judd Apatow's movies, Knocked Up brings the whole gang—Seth Rogen, Jonah Hill, Jason Segel, and more—together for a movie about having fun, being in an adult relationship, and growing up when you really need to.
10 Things I Hate About You (1999)
One of the most charming movies on the list—and just a genuine feel-good flick—is a modern Shakespeare re-telling with a cast that features young Joseph Gordon-Levitt, Julia Stiles, and may have been the first star-making performance for the late Heath Ledger.
Plus One (2019)
You should really check out Plus One. Bringing together stars of two of your favorite shows—Jack Quaid from The Boys and Maya Erskine from Pen15—Plus One tells the story of platonic friends who decide they'll get through what looks to be a grueling wedding season by being each other's plus ones when they need to be. The movie has a lot of heart, and some huge laughs—courtesy of the movie's smart writing and its incredibly talented leads.
Someone Great (2019)
Someone Great might be closer to a dramedy or, like, an anti-romcom than a true romcom, but its got a great cast—Gina Rodriguez, Lakeith Stanfield, Brittany Snow, among others—and even better music. You'll laugh, you'll cry, but by the end you'll just be happy that you watched a damn g0od movie.
13 Going On 30 (2004)
Jennifer Garner was best known for her action roles in Alias and Daredevil when 13 Going on 30 came out, but she's got so much charming charisma going for her as a kid in an adult's body (kind of a take on Big) that she instantly became known as a comedy powerhouse in addition to her action chops. Bonus points for Mark Ruffalo, Judy Greer, and Andy Serkis.
When Harry Met Sally (1989)
One of the all-time romcoms, When Harry Met Sally finds genre staple Meg Ryan and Billy Crystal both at their absolute best—and funniest. Rob Reiner was perhaps the best director in the world in the late 80s and early 90s—with When Harry Met Sally, Misery, Spinal Tap, Stand By Me, and The Princess Bride all to his name—and this movie is a very clear argument for that point. I'll have what she's having!
Something's Gotta Give (2003)
An incredible love triangle emerges between Diane Keaton, Jack Nicholson, and Keanu Reeves. Seriously, what more can you ask for?
High Fidelity (2000)
High Fidelity, based on the novel of the same name, is a touchstone. What do you get when you look at music snob who realizes he may have messed up every relationship he's ever had in his entire life? Or maybe they're the ones who messed up. Either way.
High Fidelity (2020)
Sound familiar? This series starring Zoë Kravitz was unjustly cancelled by Hulu after only one season, but it's a wonderfully-updated modern-day take on the original. Kravitz is always a treat to watch, but her take on the character played in the film by John Cusack might be her career-best.
Forgetting Sarah Marshall (2008)
Have you ever heard anyone say a single bad thing about Forgetting Sarah Marshall? No, you haven't. Because it is perfect and Jason Segel is perfect.
The Wedding Singer (1998)
The competition is tough, but The Wedding Singer—an '80s set film that was the first of three Adam Sandler/Drew Barrymore pairings—might be top dog in the all-time Sandler catalogue. Sweet, memorable, and funny, The Wedding Singer has great music and great performances, even if it hits most of the familiar genre beats you expect it to.
Intolerable Cruelty (2003)
Take the sharp writing and fun situations The Coen Brothers previously cooked up in movies like Fargo and apply it to the world of divorce law. George Clooney and Catherine Zeta-Jones are naturals with snappy dialogue.
Silver Linings Playbook (2013)
Silver Linings Playbook is a rarity in the romcom world: an awards darling. Jennifer Lawrence won the Oscar, and Bradley Cooper, Robert De Niro, and Jackie Weaver were all nominated for this perfectly-paced story of finding romance with the hand you're dealt. Also one of the better depictions of mental illness in recent memory.
The Holiday (2006)
One of a handful of modern holiday classics that have been immortalized in pop culture (and worthy of spots on this list). A fantastic cast here of Kate Winslet, Cameron Diaz, Jude Law, and Jack Black.
Fleabag (2015, 2019)
Phoebe Waller-Bridge rode the second season of Amazon Prime Video's Fleabag to superstardom, but both seasons of her third-wall-breaking series are simply spectacular exercises in character building. Her titular character isn't just flawed; in addressing the viewer constantly, we feel a kin to her, for all of her funny highs and tragic lows.
Schitt's Creek (2015-2020)
From one Emmy's darling to another. Schitt's Creek is a great show with comedy that can make you laugh at any moment, and long-running romantic subplots to keep you invested from start to finish.
What If (2014)
Harry Potter and Kylo Ren take on a romantic comedy. No, but seriously—What If certainly follows the formula that most of this list's entries do, but Daniel Radcliffe and Adam Driver (and Zoe Kazan and Mackenzie Davis as their love interests) are so charming that it makes this a movie that will have you laughing while you hope everything works out in the end.
That Awkward Moment (2014)
A super trio (Zac Efron, Michael B. Jordan, and Miles Teller) have all recently ended relationships, and really just want to be single for as long as possible. It's a movie, so that doesn't last long. But how is it gonna be messed up? And how are they all gonna end up in love with someone? If you just accept that you probably know how it's going to turn out, the mystery of the journey there can be all the fun.
It's good. Is it one of Zac Efron's best? Well, we've got a different story to decide that.
She's The Man (2006)
She's The Man showed the sheer comic ability of Amanda Bynes at the peak of her abilities, and also introduced the world to Mr. Channing Tatum. Mission accomplished on all fronts.
Easy A (2010)
Easy A might be the best teen romcom of the last 20 years or so. Not only does it have Emma Stone at her most charming in the lead, but it's got the aforementioned Amanda Bynes in a very funny supporting role, Penn Badgley as a love interest, and Stanley Tucci and Patricia Clarkson as loving and supportive parents. Add in a very funny and breezy storyline that references The Scarlet Letter and you've got a modern classic.
500 Days of Summer (2009)
One of the most visually stylish movies on the list, 500 Days of Summer is a fantastic film behind a pair of great leads in Joseph Gordon-Levitt and Zooey Deschanel. One important thing to remember? You're not exactly watching a healthy relationship play out on screen. That's the point.
The 40-Year-Old Virgin (2005)
Another Judd Apatow entry, The 40 Year Old Virgin was the breakthrough performance for one of America's favorite comedic performers: Steve Carell. The movie is about, well, exactly what the title says its about. Catherine Keener is a great love interest, and young Elizabeth Banks, young Seth Rogen, and ageless Paul Rudd are particularly excellent support. Keep an eye out for cameos for a couple future superstars, too.
Crazy, Stupid, Love (2011)
When you think about the writing that Dan Fogelman—who was behind Crazy, Stupid, Love—has done in the years since this movie has been released, things start to make a lot more sense, (Fogelman has blown up with his show This Is Us, but also made the film Life Itself and the one-season wonder baseball show Pitch). He's got the kind of writing that has the tricks that can make you laugh and feel like a gut punch all at the same time when you realize what, exactly, is going on. And when you've got Steve Carell, Ryan Gosling, Julianne Moore, and Emma Stone reading those lines, well, uh, it's gonna work.
Friends With Benefits (2011)
Justin Timberlake and Mina Kunis are funny! In this movie that is totally harmless. Watch it, laugh a few times, forget it, watch it again in a year or two. There's a place for this sort of movie! And it's right here. And also on FX when you're randomly channel surfing.
Never Been Kissed (1999)
Can't Hardly Wait (1998)
OK. So. You know how the best parts of every teen comedy are usually the party scene? Where there's usually a few people who are way too drunk, maybe an unlikely couple are paired off, some classic era-appropriate music plays, and just great times are had by all? The entire movie of Can't Hardly Wait is a party scene, and it's got romantic scenes that are (for the most part) not gag-worthy. It's one of the best of the genre and pretty damn timeless.
Empire Records (1995)
It's Rex Manning day! You may have heard that said an April 8th or two, and know now and forever that it's a record to the timeless, maybe not masterpiece but definitely beloved film Empire Records. Great soundtrack, entertaining characters, and characters you may or may not root for. It's a classic whether you like it or not.
Trainwreck (2015)
Amy Schumer was already on an upward trajectory in 2015 with her Comedy Central sketch comedy series Inside Amy Schumer, but her star really blew up when Trainwreck was released. The movie stars Schumer as a magazine journalist assigned to do a story on a sports doctor (Bill Hader) who counts LeBron James (hilariously playing himself) as one of his best friends. Brie Larson and Mike Birbiglia are among a few others who contribute laughs in yet another Judd Apatow modern favorite.
Set It Up (2018)
Sometimes you just need charming people to make your romcom work. Glen Powell and Zoey Deutch (along with Taye Diggs and Lucy Liu) accomplish that in Set It Up, which doesn't reinvent the wheel at all, but definitely is a wheel that you'd be happy to ride as a unicycle anywhere you're trying to go. I don't know what that analogy is, but this movie is good. Watch it.
When We First Met (2018)
Another one that doesn't really reinvent the wheel, When We First Met is just a charming film that makes pretty good use of Adam Devine's Jack Black-meets-Ryan Reynolds screen persona.
Insecure (2016 - )
Issa Rae's star vehicle (she's also appeared in movies like Little and The Lovebirds) is this Emmy-nominated TV series which has become one of the most popular on TV. Issa manages and balances her relationships and friendships throughout the show's four seasons (so far) in a typically hilarious manner. Her co-stars, Jay Ellis and Yvonne Orji are also top notch.
I Love You, Man (2009)
I Love You, Man opens where most romcoms end: the guy proposing to the girl. Where this movie finds itself, though, is when the girl (Rashida Jones) convinces the guy (Paul Rudd) that he needs to find some friends—male friends, in particular. The guy then begins his hunt for a best man, eventually finding someone (Jason Segel) who he thinks just might be "the one." The bromance movie to end all bromance movies.
Dollface (2019)
After however many years on 2 Broke Girls, Kat Dennings broke the mold with her Hulu original series Dollface. It's another sort of anti-romcom, where the idea is that her (previous) romantic relationship has held her back from what she could have been getting out of life. Dennings is always a great dry humorous presence, and that's no difference in Dollface.
Nick and Norah's Infinite Playlist (2008)
And one of the places where we previously knew of Dennings' talent for romcoms was in the late-aughts classic Nick and Norah's Infinite Playlist. The movie finds Michael Cera at peak-awkward Michael Cera time, and he and Dennings have really great chemistry. Warning: this movie may make you long for a time when hanging out at concerts and concert venues was safe and a thing that happened.
Juno (2007)
Like Silver Linings Playbook, Juno was a rare romantic comedy that actually was so beloved and acclaimed upon release that it actually garnered several Academy Award nominations. Cera is doing his thing once again, along with a great Eliot Page lead performance as the titular pregnant character. Jennifer Garner, Jason Bateman, JK Simmons, and Alison Janney are all great in support.
The Five-Year Engagement (2012)
The Five-Year Engagement is sort of a spiritual successor to Forgetting Sarah Marshall. Jason Segel here is paired with Emily Blunt, and they have friends played by Chris Pratt and Alison Brie. It doesn't quite live up to Sarah Marshall standards, but it's fun and proves worthy of its impressive cast.
Always Be My Maybe (2019)
Netflix really has a good thing going with some of these romcoms, huh? Always Be My Maybe is great, largely in part due to its two very likable—and very funny—leads, Ali Wong and Randall Park. And, uh, can we talk about that epic cameo? You know the one. You definitely know the one.
Clueless (1995)
Paul Rudd in 2020: delightful. Paul Rudd in 1995: delightful. "Paul Rudd: always delightful" may be the moral of life these days, but it may have first been put into existence in his role as Josh, stepbrother to Alicia Silverstone's Cher Horowitz in the unforgettable Amy Heckerling comedy Clueless. Maybe the most quotable movie on the list? It's up there.
They Came Together (2014)
Paul Rudd in 1995, Paul Rudd in 2014—what's the difference? Here he's one half (along with Amy Poheler) of a rather genius send-up of the whole romcom genre, from his old buddy David Wain. The pair had previously worked together on Wet Hot American Summer, The Ten, Role Models and Wanderlust.
Crazy Ex-Girlfriend (2015-2019)
This series, which ran for four seasons, really made the talent of its star and creator, Rachel Bloom, apparent. With hysterical writing, including amazing songs co-written by the late Adam Schlesinger of Fountains of Wayne, this is one of the more underrated shows of the last decade.
How to Lose a Guy in 10 Days (2003)
Matthew McConaughey was in a lot of, um, forgettable romantic comedies in the 2000s, but perhaps the most memorable of those was How To Lose a Guy in 10 Days, which saw him play the romantic counterpart/foil (and titular "guy") to Kate Hudson's lead magazine writer. It is very much a product of 2003, and feels very 2003, but it's certainly got its charms. If you're looking for a romcom, it's hard to go wrong with this one.
Safety Not Guaranteed (2012)
Romcoms can sometimes span genres. Enter Safety Not Guaranteed, a romcom that veers into adventure and sci-fi territory at times. With a cast that includes Aubrey Plaza, Mark Duplass, and Jake Johnson, this was one of the more underrated movies of the 2010s.
Selfie (2014)
This sitcom only lasted a single season, but with John Cho (Star Trek, Searching..., the Harold and Kumar films) and Karen Gillan (Guardians of the Galaxy, Jumanji: Welcome to the Jungle) as its leads, this sitcom was smart, charming, and most important for the purposes of this list: funny.
This is not currently streaming but we will update this space when it is!
50 First Dates (2004)
Adam Sandler and Drew Barrymore brought the Wedding Singer band back together for 50 First Dates, another charming, delightful, and funny movie that plays into the strength of the Sandman/Drew relationship and chemistry.
Obvious Child (2014)
Obvious Child finds Jenny Slate (Saturday Night Live, Big Mouth) in the spotlight, and she really shines. She plays a stand-up comedian who finds herself pregnant after a one-night stand; the rest of the film, simply enough, finds her navigating the aftermath with her suitor (played by Jake Lacy, who has become a big time 'that guy' in comedy shows and movies).
Palm Springs (2020)
In a year as strange as 2020, it's fitting that one of the funniest—and, really, best—movies of the year was an Andy Samberg-led comedy that debuted on Hulu. Samberg and Cristin Milioti (Black Mirror, How I Met Your Mother) play a guy and a girl who are stuck in a Groundhog Day-esque time loop at a tropical wedding. Sounds basic enough, but Palm Springs, which also stars JK Simmons and Peter Gallagher, among others, is smart when it needs to be, and uses its sci-fi bonafides to perfection.
Mike and Dave Need Wedding Dates (2016)
Adam Devine and Zac Efron play the Mike and Dave of the title. Aubrey Plaza and Anna Kendrick play the wedding dates of the title. Hilarity, as you might expect, ensues.
Happiest Season (2020)
2020, the year when movies land on one of the big streaming services and everyone somehow talks about those same movies for a few days at a time. If you somehow haven't seen Happiest Season yet, hop on it: this romcom, which stars Kristen Stewart and Mackenzie Davis as a couple who have to hide their relationship from Davis' conservative family during a holiday season visit, is one of the buzziest streaming debuts of the year. And whether you like it or not (and you'll probably enjoy quite a bit of it), you'll definitely have something to talk about at the end. Bonus: supporting role by Schitt's Creek star Daniel Levy.
Love Actually (2003)
From a movie that might just maybe become a holiday classic, we go to the romcom that 100% definitively is a modern holiday classic. Love Actually is flawed, but once you've seen it 100 times or so, you tend to overlook those flaws and just enjoy the cornball story that will make you feel good, or sometimes feel bad. And there's also Billy Mack, who might just be the greatest holiday movie character in the history of film.
Bridesmaids (2011)
Bridesmaids is so funny—with a cast led by the excellent Kristen Wiig, Melissa McCarthy, Rose Byrne, and Maya Rudolph—that you almost forget that it's also a top-shelf romantic comedy. Sure, Wiig has a flirtation throughout the movie with asshole hot guy Jon Hamm, but how could anyone not fall for nice funny guy Chris O'Dowd? A serious conundrum, but quite the funny one along the way.
Along Came Polly (2004)
Along Came Polly is a pretty standard mid-2000s romantic comedy, but Ben Stiller and Jennifer Aniston are both known quantities: you know what you're getting with them, and its mostly good. That being said, you're really coming here for two supporting performances: Philip Seymour Hoffman's incredibly funny 'best friend' turn, and a pretty small cameo from Hank Azaria as a scuba instructor. Unforgettable and unbelievably funny.
Meet The Parents (2000)
While we're on the Ben Stiller train, let's talk Meet The Parents. This is a romantic comedy, but, again, not in the way you might think. Stiller plays Greg Focker, a nice guy with a pretty stable relationship—it's her parents, played by Robert De Niro and Blythe Danner, who he really needs to work his magic on. De Niro and Stiller have such a natural and funny chemistry that this is a rare comedy with not just one but two sequels (2004's Meet The Fockers is solid, but let's not talk about 2010's Little Fockers). It's not romantic, per se, between De Niro and Stiller, but there's clearly a lot of that unspoken 'guy love' that we hear so much about.
There's Something About Mary (1998)
One more for this Ben Stiller streak we're riding. There's Something About Mary was one of the biggest comedies of the '90s, and for good reason. Stiller and a scumbag private eye played by Matt Dillon are among the many competing for the romantic attention of Mary (Cameron Diaz). The movie is funny and gross in all the right ways. Also includes one of the greatest on-screen fights between man and dog.
Little Shop Of Horrors (1986)
Romcoms go horror! Romcoms go musical! Romcoms go horror musical! I mean, come on. Little Shop of Horrors is such a classic, and one that will have you cracking up—Steve Martin's role is perfect—one moment, charmed by Rick Moranis the next, and kind of scared of the giant man-eating plant the next. This movie is pretty damn perfect, so we're a little eager to see how the remake—with Chris Evans in Steve Martin's role!—turns out.
The Princess Bride (1987)
We've already touched on this, but Rob Reiner was on such a heater in the late '80s. That included The Princess Bride, which is part parody, part meta-comedy, and part fantasy romcom. In short, it's basically everything you want in an entertaining movie. Robin Wright and Cary Elwes are perfect, and the Mandy Patinkin role is one that has us shouting 'That's our Mandy!" at the screen every few minutes.
Long Shot (2019)
Seth Rogen makes another appearance on the list in this charming film that finds him as a journalist who runs into his old babysitter—who just happens to be running for President of the United States. The movie is super funny and Rogen and Charlize Theron—who plays his old babysitter—are great together.
Adventureland (2009)
Kristen Stewart has been good at this for a while. Long before we wanted the best for her in Happiest Season, we saw her in the post-grad years of Adventureland, alongside Jesse Eisenberg, Ryan Reynolds, Bill Hader, and Kristen Wiig, among others (this cast aged well, huh?). It's a coming-of-age dramedy romcom set in a 1987 amusement park—a perfect recipe for laughs and memorable scenes. A great soundtrack doesn't hurt, either.
Top Five (2014)
Chris Rock wrote, directed, and starred in Top Five, which sort of feels like his take on an Annie Hall-type movie. Rock plays a movie star making a comeback after a few ill-advised choices, and Rosario Dawson (recently seen in The Mandalorian) plays the NYT journalist writing a piece on him. A funny, memorable, and rather charming movie. The title is a reference to several characters in the movie listing their top five favorite hip-hop artists, so naturally the soundtrack is fantastic to match.
Mamma Mia! (2008)
It's funny. It's delightful. IT'S PERFECT. And come on, those ABBA songs are always catchy and you know it.
Wedding Crashers (2005)
Wedding Crashers gets a little crude at times, but just go in expecting to grimace a little bit, and you'll get one of the funniest movies of the 2000s. It's not out there at all to call Wedding Crashers a modern classic, based on the strength of Owen Wilson and Vince Vaughn's performances. But what people might forget is that the movie actually also has a lot of heart—again, thanks to the great work from its two stellar leading men.
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December 11, 2020 at 02:39AM
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