Rom-com bracket: Vote on the field of 68 contenders

Image by Zoë Ryan

Image by Zoë Ryan

Welcome to the great rom-com bracket of 2019! In honor of the 30th anniversary of When Harry Met Sally, Zoë Ryan and I are setting out to determine the best romantic comedy of the past 30 years. Yesterday we laid out the rules of the bracket, and today we are introducing the movies contending for the top spot.

Here’s how this will work: Zoë and I will break down each of the matchups below. There will be voting buttons with each matchup below that you can use to cast your vote. If you don’t want to scroll through all of our fascinating insights, you can also check out the voting page here: rom-com voting page.

For the sake of simplicity, Zoë and I already decided the play-in matchups ourselves.

You can track the results and view the full bracket by clicking here: full rom-com bracket.

Let’s get to it.

The Play-In Games

(16) 27 Dresses vs. (16) Trainwreck

The matchup: An Apatow gal grudge match between a woman who serves as a bridesmaid 27 times and a woman who doesn’t even believe monogamy is possible.

Our Thoughts:

JS: I’m surprised at how low Trainwreck was rated on IMDb; it should have made the field outright. 27 Dresses is standard fare, and it’s not even the best Katherine Heigl rom-com in the field. I’m going with Trainwreck, a welcome addition to the raunch-rom-com genre. Shoutout to perennial rom-com side character Judy Greer for 27 Dresses, though.

ZR: Just like Katherine Heigl, 27 Dresses is very white, very bland, and very forgettable. Trainwreck gets my vote for being marginally less white and showing us that Bill Hader is hotter than we realized.

Winner: Trainwreck

(16) 13 Going on 30 vs. (16) Runaway Bride

The matchup: A woman who magically jumps forward in time versus a woman who wishes she could go back in time and undo a few marriages.

Our Thoughts:

JS: Julia Roberts is, after Meg Ryan, the rom-com GOAT. But in Runaway Bride she and Richard Gere could not rekindle the Pretty Woman magic, and it’s a pretty flat film. My vote goes to 13 Going on 30, for the ever-flustered greatness of Jennifer Garner and yet another supporting rom-com turn from Judy Greer.

ZR: Ariana recognized the greatness of 13 Going on 30 and so do I. Runaway Bride is flat and they named Richard Gere’s character “Ike,” which may be the least sexy name in history. Thank you, next.

Winner: 13 Going on 30

(16) The Five-Year Engagement vs. (16) Never Been Kissed

The matchup: It takes a couple five years to learn what they really want out of their relationship; it takes a reporter one undercover semester at a high school to fall in love with her teacher.

Our Thoughts:

JS: Never Been Kissed is a movie about an undercover reporter falling for her high school teacher, but it’s also about that teacher falling for who he think is a 17-year-old student, and that made me squirm. It’s also maybe the most ridiculous example of how little Hollywood screenwriters understand about the newspaper industry. The Five-Year Engagement is my pick for a great Emily Blunt performance.

ZR: Never Been Kissed is a much stranger movie than I initially remembered and features yet another bad Drew Barrymore haircut. The Five-Year Engagement not only has better haircuts, but also a much stronger plot and great performances from Emily Blunt and Alison Brie.

Winner: The Five-Year Engagement

(16) Sweet Home Alabama vs. (16) Along Came Polly

The matchup: The “I’m getting married but I’m having second thoughts because I’m in love with someone from my childhood” matchup.

Our Thoughts:

JS: Not a huge fan of Ben Stiller or ferrets, so this one is a pretty easy call for me. Sweet Home Alabama has to advance because, despite an absurd amount of screen time devoted to sympathizing with characters who love the Confederacy, Reese Witherspoon is electric. (Lightning strike pun fully intended.)

ZR: I was surprised that this was the only appearance for both Reese Witherspoon and Jennifer Aniston, both of whom I consider to be major rom-com players. While both movies are fine, if somewhat bland, Sweet Home Alabama takes it thanks to the iconic “when the lightning hits the sand” moment.

Winner: Sweet Home Alabama

The Annie Hall region

(1) Wall-E vs. (16) Trainwreck

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The matchup: A lonely robot is willing to travel to outer space to pursue his love, while Amy Schumer struggles to make it work with a man in her own city.

Our thoughts:

JS: Let me stop you right there: yes, Wall-E is a rom-com. And while it may not be iconic within the genre, it is beloved enough to earn a 1-seed in this field. I’m not voting for Wall-E because it’s the better movie, though, but because it’s the better romance. The fire extinguisher in space scene is an all-time romantic gesture.

ZR: Is Wall-E truly a rom-com? No. Is Trainwreck? Yes.

Your vote:

(1) Wall-E vs. (16) Trainwreck

(8) Pretty Woman vs. (9) Waitress

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The matchup: The unequal power dynamics showdown, between a prostitute who falls for her client and a pie-maker who falls for her doctor.

Our thoughts:

JS: One of the most brutal first-round matchups for me. I’m a BIG Waitress stan, and Keri Russell is just incredible. But Julia Roberts is an unstoppable force of nature in Pretty Woman. I can’t vote against that laugh.

ZR: If you vote against Pretty Woman, I’m not sure you can call yourself a rom-com fan.

Your vote:

(8) Pretty Woman vs. (9) Waitress

(4) Crazy, Stupid, Love vs. (13) Reality Bites

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The Matchup: A bunch of storylines all come together to celebrate the power of love; a group of recent college grads hardly even knows how to think about what “love” means.

Our thoughts:

JS: I just re-watched Crazy, Stupid, Love, and wow oh wow does it not hold up well. The babysitter plot line makes me very uncomfortable, Emma Stone is not in the movie nearly enough, and nearly every line just feels like it was written by a movie studio executive. I’m going with Reality Bites, because all we need in this life is you and me and five bucks. And also because I’m in love with 90s Winona Ryder.

ZR: Going to be honest, I haven’t seen Reality Bites. That said, I watched Crazy, Stupid, Love in theaters five times (it was a slow summer). This is the film that led to Emma Stone and Ryan Gosling saving jazz and it should move forward for their chemistry in the Dirty Dancing scene alone.

Your vote:

(4) Crazy, Stupid, Love. vs. (13) Reality Bites

(5) Grosse Pointe Blank vs. (12) My Big Fat Greek Wedding

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The matchup: A hitman returns to his hometown for a job and reconnects with his high school sweetheart, and a woman who’s never left her hometown finds a sweetheart of her own.

Our thoughts:

JS: My Big Fat Greek Wedding is one of the most iconic rom-coms ever, and one of the most financially successful. It’s also...incredibly boring? There’s no tension? I’m going with the gleefully violent Grosse Pointe Blank for John Cusack’s perfectly odd comedic timing and the radiant Minnie Driver.

ZR: This is more a vote against Grosse Pointe Blank, which I found a little too violent for casual rom-com viewing. So I’m pushing through My Big Fat Greek Wedding on a technicality, while acknowledging it suffers from the same plight of Crazy Rich Asians and The Big Sick, which also centered around a significant other meeting the family and are actually probably better movies.

Your vote:

(5) Grosse Pointe Blank vs. (12) My Big Fat Greek Wedding

(2) As Good As It Gets vs. (15) Two Night Stand

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The matchup: Two very nice women fall for assholes who learn how to not be assholes.

Our thoughts:

JS: I can’t believe it, but I’m going with Two Night Stand. I was so, so certain I was going to pick As Good As It Gets...until I revisited it. Jack Nicholson’s character is so damn horrible to everyone, and I don’t buy for a second that Helen Hunt would fall for him. Two Night Stand is a low-key innovative rom-com about sexual consent, and I care way more about its central couple.

ZR: Two Night Stand is weirdly better than you expect and more accurately depicts millennial relations than the vast majority of these movies. As Good As It Gets is yet another film about older white people except Nicholson lacks any of the charm of Martin or even Baldwin.

Your vote:

(2) As Good As It Gets vs. (15) Two Night Stand

(7) Ruby Sparks vs. (10) Sleepless in Seattle

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The matchup: A man who imagines the perfect woman in a book versus a woman who imagines the perfect man on the radio.

Our thoughts:

JS: Sleepless in Seattle is a classic for the genre, and anything Nora Ephron makes deserves consideration. But it’s the worst of her iconic rom-com trifecta, due mostly to the fact that Hanks and Ryan hardly even get to spend any time together on screen. Ruby Sparks is a surprisingly dark film about male projection that I think might actually qualify as a horror movie, but it gets my vote.

ZR: Sleepless in Seattle may be the weakest of the Ephron trilogy, but that shouldn’t discount it from moving forward. Ruby Sparks held a mirror up to what we already knew: so-called nice guys are often the most terrifying. But I’m not looking for reality in my romantic comedies, so Sleepless in Seattle is getting my vote.

Your vote:

(7) Ruby Sparks vs. (10) Sleepless in Seattle

(3) Love, Simon vs. (14) Top Five

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The matchup: A gay high schooler strikes up a romance with an anonymous writer online; Chris Rock strikes up a romance with an anonymous writer in real life.

Our thoughts:

JS: Love, Simon is a beautiful love story that made me cry multiple times. But while I do think it qualifies as a rom-com (the romance is truly the driving force of the movie), a large portion of it is about Simon’s struggle with identity and self-discovery. Top Five is a story about two selfish people who become better people through their love for each other, and Rosario Dawson is gorgeous. It gets my vote.

ZR: Going to level with you guys. I didn’t see either of these movies...I know I know, I’m a bad bracketeer. Based on the trailer though, I’m more inclined to watch Top Five before we write the next round, so that’s getting my vote.

Your vote:

(3) Love, Simon vs. (14) Top Five

(6) Forgetting Sarah Marshall vs. (11) The Wedding Singer

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The matchup: Two men who try to get over their rude ex-girlfriends by pursuing women who are almost certainly too good for them.

Our thoughts:

JS: Zoë and I recently watched The Wedding Singer and we could barely pay attention because it just isn’t very good. Drew Barrymore’s character has few defining qualities aside from being in love with Adam Sandler, and Adam Sandler really can’t sing for a movie about a guy whose job it is to sing. Pretty solid final romantic gesture, though. Anyway, I’m picking the vastly superior Forgetting Sarah Marshall.

ZR: To put it nicely, The Wedding Singer is bad. Discounting the fact that it’s arbitrarily set in the 80s and Barrymore’s hairstyle is an insult to hair, neither character seems to have a lot of driving them forward and by the time we get to the romantic gesture, I’m kind of hoping they both die on the plane. Forgetting Sarah Marshall is an all-time classic.

Your vote:

(6) Forgetting Sarah Marshall vs. (11) The Wedding Singer

The Sugar Kowalczyk region

(1) Sing Street vs. (16) 13 Going on 30

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The matchup: The drastic measures for love matchup: a boy starts a band to impress the girl he loves, and a woman fast forwards in age 17 years to win over the man she loves. Ok, fine, that one was an accident.

Our thoughts:

JS: 13 Going on 30 is the bigger classic for the genre, and I almost want to pick it for the “Thriller” scene alone. But Sing Street is an absolute gem, and I’m already singing “Drive It Like You Stole It” in my head.

ZR: 13 Going on 30 has all of the makings of a classic. Judy Greer, a magazine that might go under, a fun dance number. But Sing Street has much more emotional heft to it, making it the clear winner.

Your vote:

(1) Sing Street vs. (16) 13 Going on 30

(8) Crazy Rich Asians vs. (9) 50 First Dates

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The matchup: A woman who can’t remember her friends and family versus a man who often wishes he could forget his.

Our thoughts:

JS: Crazy Rich Asians is a lot of fun, but it’s not a good sign that my defining memory of the movie is Awkafina, and not the central couple. The movie was more about the spectacle of Singaporean decadence and representation on screen. 50 First Dates, while filled with some unfortunate Adam Sandler gags, has a more endearing romance at its core.

ZR: I really want to vote for Crazy Rich Asians because it demonstrated that a Chinese-American economics professor could be a romantic lead in a wildly popular movie. However, I ended up feeling more invested in Constance Wu’s game theory lecture than in her relationship with Henry Golding. While it feels weird to say that I was rooting for Adam Sandler, 50 First Dates is much more satisfying as a romantic comedy.

Your vote:

(8) Crazy Rich Asians vs. (9) 50 First Dates

(4) The Big Sick vs. (13) Mr. and Mrs. Smith

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The matchup: Two movies where the prospect of death is keeping a marriage apart.

Our thoughts:

JS: Mr. and Mrs. Smith is better for the iconic real-life romance it started than the romance of the movie itself. The Big Sick was in the classic rom-com mold yet felt completely new. It has some of the most heart-wrenching scenes in any movie in recent years, and also one of the single funniest jokes in rom-com history.

ZR: While I love the Big Sick (Chicago! Diversity! True Story!), it suffers from the same problems as other early outs where the story focuses too much on the family and not enough on the romance. Plus, Emily spends the movie in a coma. Mr. and Mrs. Smith is super steamy and kick started the Brangelina powerhouse.

Your Vote:

(4) The Big Sick vs. (13) Mr. and Mrs. Smith

(5) Punch-Drunk Love vs. (12) Friends with Benefits

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The matchup: Two people who can’t seem to make healthy choices versus a man who can’t stop buying Healthy Choices.

Our thoughts:

JS: Friends with Benefits is odd: it’s a movie that tries to subvert rom-coms (casual sex is more natural than monogamy!) but ends up hitting all the beats of the genre. Punch-Drunk Love is odd because, well, it’s a Paul Thomas Anderson movie, and he makes odd movies. It doesn’t move like a conventional rom-com, but the tender romantic gesture hits me emotionally more than the gaudy flashmob in Benefits. Punch-Drunk Love it is.

ZR: I’m not sure that Friends with Benefits is trying to subvert rom-coms, but perhaps I’m overestimating the self-awareness of movie studios. Either way, Punch-Drunk Love easily takes the win this round for the sweetness at the core of this oddly dark film. Also, why don’t we ever get to see more of THIS Adam Sandler?!

Your vote:

(5) Punch-Drunk Love vs. (12) Friends with Benefits

(2) About Time vs. (15) My Best Friend’s Wedding

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The matchup: A man time travels to improve upon the romantic failures of his past, while a woman tries to break up the marriage of her best friend to make up for the romantic failures of her own.

Our thoughts:

JS: I thought About Time might be a sleeper pick in this bracket, so I was surprised to see it so highly rated on IMDb. From the director of Love Actually, it’s a truly moving film about love and loss, and Domhnall Gleeson and Rachel McAdams are a great pairing. It gets my vote over this so-so Julia Roberts film.

ZR: More accurately, About Time is a sleeper of a film. While showcasing the ever charming McAdams, it’s ultimately a bit too sentimental and follows Groundhog Day a little too closely for my taste. My Best Friend’s Wedding subverts the genre and features that killer Roberts laugh, getting my vote for the round.

Your vote:

(2) About Time vs. (15) My Best Friend's Wedding

(7) The 40-Year-Old Virgin vs. (10) Adventureland

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The matchup: A 40-year-old virgin versus a 22-year-old virgin.

Our thoughts:

JS: The respect for The 40-Year-Old Virgin has grown steadily over the years, and it’s now rightfully considered the best of the Apatow raunch-rom-coms. Yet like most Apatow movies, a lot of the jokes don’t age well, and it isn’t nearly as forward-thinking about sex as it might think it is. I’m going with Adventureland even though it will probably lose, because we just don’t appreciate Kristen Stewart enough.

ZR: I watched The 40-Year-Old Virgin recently and was surprised to see how much it held up compared to other early 2000s rom-coms. It’s not particularly progressive, but the love story at the core is quite sweet and it’s nice to see people of color in a genre that is usually white with a capital W. Adventureland is insightful and nostalgic, but I don’t remember it being particularly laugh out loud funny and thus the adventure will have to end in Round One.

Your vote:

(7) The 40-Year-Old Virgin vs. (10) Adventureland

(3) Love Actually vs. (14) Set It Up

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The matchup: Eight couples try to work out their love lives; a pair of employees try to arrange their bosses’ love lives to get out of work.

Our thoughts:

JS: Ugh. Love Actually is a powerhouse and is almost synonymous with the modern rom-com, but I’m sorry, it just doesn’t work and I don’t care about a majority of the vignettes. I could watch Set It Up a hundred times and not get sick of the chemistry between Glen Powell and Zoey Deutch.

ZR: As much as it pains me, I have to agree with Jake and go with Set It Up here. Unlike Jake, I thoroughly enjoy Love Actually and watch it every Christmas (I mean, that caroling scene), but Powell has me convinced that salamanders are romantic creatures and that kind of charisma should be rewarded.

Your vote:

(3) Love Actually vs. (14) Set It Up

(6) Submarine vs. (11) While You Were Sleeping

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The matchup: A high school boy falls in love with someone he’s trying to sleep with; a woman pretends to be in love with a man who can’t stop sleeping.

Our thoughts:

JS: Most of While You Were Sleeping is fine. Then comes Sandra Bullock’s tearjerker wedding day speech, an all-timer. Is it enough to overcome the joyous, criminally underseen, British Wes Anderson fan fiction that is Submarine? No.

ZR: Enough with the wedding day speeches. I already voted for The Proposal, so I take no issue with not pushing through the very blah While You Were Sleeping. While Submarine does veer pretty heavily into coming-of-age territory, it never falls into the common pitfalls of movies about losing one’s virginity and features a genuinely tender romance at the center.

Your vote:

(6) Submarine vs. (11) While You Were Sleeping

The Princess Ann Region

(1) Amelie vs. (16) The Five-Year Engagement

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The matchup: Whimsy leads the way to love for a French oddball, while real life problems get in the way of love for an American couple.

Our thoughts:

JS: Just like Zoë did with Trainwreck earlier, I’m voting for the 16 over 1 upset here. The Five-Year Engagement is thoroughly underrated, and it’s not a great sign for the romance that I can barely remember who Amelie’s romantic counterpart is in that film.

ZR: As much as it pains me, I am also moving The Five-Year Engagement forward. Despite watching the film four times on a flight to the UK, I had to look up Amelie to see if there was a romance in the film at all.

Your vote:

(1) Amelie vs. (16) The Five-Year Engagement

(8) Knocked Up vs. (9) Wedding Crashers

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The matchup: The raunch rom-com showdown, where characters must either get pregnant or infiltrate dozens of weddings in order to grow up and find love.

Our thoughts:

JS: About 30 minutes into Wedding Crashers I thought I might end up picking it here. But it gets worse with every passing minute, 83% of the lines are spoken by men, and there’s some pretty cavalier jokes about rape. Knocked Up has its issues, but it’s pretty sweet in the end.

ZR: I watched Wedding Crashers last weekend and I’m mostly just confused why people like this movie. From a plot and performance standpoint, it is a solid okay and are we going to gloss over the fact that Fisher assaults Vaughn? Sure, Knocked Up is yet another film about a shlubby guy getting with a beautiful girl, but it has a truly sweet romance at its core and will be getting my vote.

Your vote:

(8) Knocked Up vs. (9) Wedding Crashers

(4) Scott Pilgrim vs. the World vs. (13) You’ve Got Mail

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The matchup: The internet-inspired showdown: Scott Pilgrim takes down seven evil exes video game-style to win the girl of his dreams, while Tom Hanks and Meg Ryan fall in love anonymously online.

Our thoughts:

JS: Honestly, the easiest “upset” in the bracket. You’ve Got Mail has to win this one in a landslide. It’s a beloved rom-com and, in my mind, still supremely underrated. It’s meme-able, it’s driven by two incredible performances, and although it wraps up too quickly at the end, the final romantic gesture is just perfect. Scott Pilgrim is fun but has some Manic Pixie Dream Girl problems, and some Scott dates a 17-year-old for a long time problems.

ZR: You’ve Got Mail hands down. Often overlooked for the weaker Sleepless in Seattle, this is the movie that made America fall in love with local bookstores and solidified Hanks and Ryan as THE rom-com pairing to end all other pairings. Scott Pilgrim is innovative and its comic-like style separates it from other films in the genre, but in no way is it brilliant enough to surpass this Ephron classic.

Your vote:

(4) Scott Pilgrim vs. the World vs. (13) You've Got Mail

(5) 10 Things I Hate About You vs. (12) It’s Complicated

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The matchup: A sister can’t date until her sister sees someone else; Meryl Streep shouldn’t be sleeping with Alec Baldwin because he’s already seeing someone else.

Our thoughts:

JS: Rom-coms skew young, so It’s Complicated is a nice change of pace, and it features a great Steve Martin performance. But come on, it’s 10 Things I Hate About You, which, side note, is an interesting rom-com in the sense that it’s pretty unclear who the “main” couple is (but pretty obvious who the better couple is).

ZR: There’s nothing inherently wrong with It’s Complicated. It features some nice white people remodeling a kitchen and reminds us that Steve Martin isn’t dead. 10 Things I Hate About You features some not-so-nice white people and makes us wish Heath Ledger was still with us, and it gets my vote.

Your vote:

(5) 10 Things I Hate About You vs. (12) It's Complicated

(2) (500) Days of Summer vs. (15) What Women Want

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The matchup: A man who discovers what every woman wants versus a man who can’t figure out what a single woman wants.

Our thoughts:

JS: I wanted to hate What Women Want for the Mel Gibson of it all, and he certainly makes the movie worse (I think if it was Tom Hanks instead it might be a rom-com classic). But Helen Hunt is great, and I have to shout out Judy Greer for another crucial rom-com supporting role that, sadly, I must cut from the opening round. (500) Days of Summer didn’t make a huge splash when it came out, but I think it’s fair to call it a bona fide modern classic, and it’s truly innovative for the genre.

ZR: What Women Want is a highly imperfect movie about a man who comes to the epiphany that women don’t like him because he’s a bad person, making this one of the easiest matchups this round. (500) Days of Summer is an almost perfect movie in my opinion, from the joyfulness of the best movie flash mob of all time to the quiet bittersweetness of the entire reality vs. expectations scene.

Your vote:

(2) (500) Days of Summer vs. (15) What Women Want

(7) Four Weddings and a Funeral vs. (10) Obvious Child

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The matchup: The pioneering Richard Curtis British rom-com versus the indie rom-com about abortion.

Our thoughts:

JS: I’m happy to finally get to this matchup so I can finally say this: HUGH GRANT PICKED THE WRONG DAMN PERSON. Andie MacDowell stinks in this movie, and Hugh Grant clearly should have fallen for Kristin Scott Thomas. Obvious Child is truly innovative for the genre, and Jenny Slate deserves to be the star of many, many more movies. *Checks IMDb* Wait, she’s only slated to be in animated movies? Ugh.

ZR: Hugh Grant may have picked the wrong woman, but  Jake made the wrong pick this round. Four Weddings and a Funeral is breezy and Hugh Grant is his usual delightful self. Obvious Child is innovative and Jenny Slate is fabulous, but this movie is driven by her pro-choice choice, not the relationship.

Your vote:

(7) Four Weddings and a Funeral vs. (10) Obvious Child

(3) Rushmore vs. (14) She’s the Man

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The matchup: Two high schoolers who try, and fail, to become men in order to get closer to the person they love.

Our thoughts:

JS: She’s The Man is underrated for just how clever it is: between all the character-jumping Amanda Bynes has to do, it’s amazing just how easily the film handles all the different romance plot lines. But while I appreciate the early break-out role for Channing Tatum, I have to pick Rushmore. I guess you just have to find something you love to watch, and then watch it for the rest of your life. For me, it’s Rushmore.

ZR: I’m not sure we can really classify a movie as a romantic comedy if the romantic feelings aren’t mutual. While She’s The Man lacks the wit of Twelfth Night, it did give audiences an early taste of the star Channing Tatum has become, including a complicated love quadrangle, and has sports. What more could you want?

Your vote:

(3) Rushmore vs. (14) She's the Man

(6) Definitely, Maybe vs. (11) Bridget Jones’s Diary

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The matchup: Two movies about career-frustrated leads who have to choose between, honestly, a handful of good romantic options.

Our thoughts:

JS: Bridget Jones’s Diary is the iconic one here, and it probably deserves to win, and maybe as a man I’m biased towards the rom-com with a male lead. (This is true.) But I’m picking Definitely, Maybe, partially because I just saw it and partially because Isla Fisher is phenomenal and should have been in about 100 more rom-coms than she has been.

ZR: Definitely, Maybe hit a personal nerve for me and for that reason alone, I found it hard to enjoy it. But even if that wasn’t the case, Bridget Jones’s Diary would take the win. The casting of Zellweger, Grant, and Firth is perfection and every scene in this modern retelling of Pride and Prejudice from the Christmas lunch to the blue soup is iconic.

Your vote:

(6) Definitely, Maybe vs. (11) Bridget Jones's Diary

The Princess Bride Region

(1) Groundhog Day vs. (16) Sweet Home Alabama

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The matchup: Two people who find love by re-living the past.

Our thoughts:

JS: The curmudgeonly Bill Murray and the radiant Andie MacDowell form the perfect pair in Groundhog Day, and it secures my vote easily. It’s a clever inverse of the normal rom-com formula: rather than become a better person because he falls in love, Bill Murray becomes a better person and is then able to fall in love. Also, I feel bad for Patrick Dempsey.

ZR: I think in a different match up Sweet Home Alabama could have been a sleeper pick. However, it doesn’t hold a candle to the sheer perfection that is Groundhog Day. Murray is at his best and that ice sculpture scene makes me tear up every single time.

Your vote:

(1) Groundhog Day vs. (16) Sweet Home Alabama

(8) Enough Said vs. (9) The Holiday

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The matchup: The written and directed by the female rom-com auteur showdown, with Nicole Holofcener’s romance between Julia Louis-Dreyfus and James Gandolfini facing off against Nancy Myers’s Kate Winslet-Cameron Diaz led country-swapping romp.

Our thoughts:

JS: James Gandolfini and Julia Louis-Dreyfus make for a strange pairing, but it works exceptionally well. The real reason I’m picking Enough Said, though, is Nicole Holofcener’s glorious script.

ZR: The Holiday features two couples for the price of one movie. Plus if we’re counting strange pairings that work especially well, my vote is for the truly bizarre coupling of Kate Winslet and Jack Black.

Your vote:

(8) Enough Said vs. (9) The Holiday

(4) Garden State vs. (13) Zack and Miri Make a Porno

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The matchup: The quintessential indie Manic Pixie Dream Girl movie versus a rom-com about porn.

Our thoughts:

JS: Zack and Miri can be sweet at times, but there are unspeakably gross scenes I won’t get into here that just go a little too far. Also, it looks like they shot the movie for like $12. Garden State has some male gaze problems, but dammit if I don’t fall for it.

ZR: Braff described Garden State as “a movie about taking action,” but if we’re being honest, it’s a movie about a sad guy who waits for Natalie Portman to take action. Zack and Miri Make a Porno, on the other hand, is about two friends who take drastic action to solve their financial woes and fall in love along the way. Plus it finally gives Elizabeth Banks, who suffers from always-the-bridesmaid syndrome, a love story of her own.

Your vote:

(4) Garden State vs. (13) Zack and Miri Make a Porno

(5) Jerry Maguire vs. (12) Hitch

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The matchup: An iconic opening line (“Life is not the amount of breaths you take, it's the moments that take your breath away”) vs. an iconic closing line (“You had me at hello”).

Our thoughts:

JS: Hitch is...fine. It has some great Will Smith moments, but then it also has moments like the time he suffers a severe allergic reaction that I really didn’t need. Jerry Maguire is an ok movie for like an hour and a half, and then at the end I balled like three separate times. I could watch this endlessly. Did you really think I was ever going to vote against Tom Cruise?

ZR: As Jake said, Hitch is fine at best. While the performances of Will Smith and Kevin James are warmhearted, the film overall is extremely predictable. Jerry Maguire easily takes the round for having one of the best closing lines in the field, if not the best closing line in any romantic comedy.

Your vote:

(5) Jerry Maguire vs. (12) Hitch

(2) Moonrise Kingdom vs. (15) Going the Distance

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The matchup: Two couples who try to overcome a great geographic distance to make their relationship work.

Our thoughts:

JS: The most notable thing about Going the Distance might be that it reminds me that we tried to make Justin Long a thing? And he was just too boring? Moonrise Kingdom is the greatest story of young love we have in this whole damn bracket. Jiminy Cricket, he flew the coop!

ZR: Jake and I didn’t even know Going the Distance was a movie until we embarked on this adventure. While it wasn’t bad, I felt all of the supporting were more compelling than the main couple. I’m way more #TeamApplegan than #TeamLongmore. The residents of New Penzance may be definitely whacky, but Sam and Suzy hold my attention (and my heart). Moonrise Kingdom is the clear winner here.

Your vote:

(2) Moonrise Kingdom vs. (15) Going the Distance

(7) Notting Hill vs. (10) Clueless

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The matchup: Two men who read a lot falling in love with women who are way, way more popular than they are.

Our thoughts:

JS: Another brutal first-round matchup for me, but I have to go with Notting Hill. I think I might like Clueless better, and it’s hilarious and so perfectly 90s. But Notting Hill has maybe the top two modern rom-com players in Julia Roberts and Hugh Grant at the peak of their powers, and the “I’m just a girl, standing in front of a boy” speech is a top-five rom-moment.

ZR: Clueless is in the high school coming-of-age category more than the rom-com bucket for me. Plus, the whole falling in love with your step-brother thing makes me feel pretty icky. This is not to say Notting Hill is getting pushed through on a technicality. As Jake said, this is Grant and Roberts at their best and I get teary just thinking about that speech.

Your vote:

(7) Notting Hill vs. (10) Clueless

(3) Silver Linings Playbook vs. (14) How to Lose a Guy in 10 Days

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The matchup: Two couples who can’t seem to shake each other, no matter how hard they try.

Our thoughts:

JS: Ok, ok, so: Silver Linings Playbook is a better movie. It just is. Jennifer Lawrence is so damn good. But it’s not good because of the romance, but because of the confluence of a lot of great acting and writing and a bangin’ dance scene. How to Lose a Guy in 10 Days is my pick.

ZR: Silver Linings Playbook may have won an Oscar, but How to Lose a Guy in 10 Days is one of the best representations of the genre. Kate Hudson? Check. A woman who works at a magazine? Check. A battle of the sexes? Check. A romance that makes me swoon every time? Check.

Your vote:

(3) Silver Linings Playbook vs. (14) How to Lose a Guy in 10 Days

(6) To All the Boys I’ve Loved Before vs. (11) The Proposal

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The matchup: Two rom-coms about people who pretend to date each other for their own selfish purposes but then fall for each other in real life. (I didn’t even plan this. It just works so well.)

Our thoughts:

JS: The Proposal is led by a powerhouse couple in Sandra Bullock and Ryan Reynolds, and it’s a little sad that Sandra Bullock might not even make it out of the first round of this bracket. But I have to go with the better movie, and it’s To All The Boys I’ve Loved Before, which is a really sweet high school romance. Also, in terms of contribution to the genre, the phenomenon that was/is Noah Centineo is a truly notable moment in rom-com history.

ZR: I know we’re in the phase of “rom-coms for nice people,” but I’m not sold on the sickeningly-sweet To All The Boys I’ve Loved Before. I’m going with The Proposal, which speaks to my cynical, workaholic soul. The script might not be very strong and sure, the plot is predictable, but the chemistry between Reynolds and Bullock is off the charts and shows there’s hope for those of us who never leave the office.

Your vote:

(6) To All the Boys I've Loved Before vs. (11) The Proposal
Jacob Skubish1 Comment