I can’t believe I got this assignment, because quite frankly, there is nothing I hate more than a wedding. Frankly, I would rather spend a long Saturday watching my great aunt Alba reorganize her mason jar collection than sit through a wedding (especially if Alba offered an open bar).  But with the opening of The Five Year Engagement (which looks to be one of the funniest wedding-themed films in recent memories) set to have moviegoers buzzing about weddings and marriage proposals, Picktainment thought this would be a perfect time to look at the best movies about weddings and engagements.


Best Movie About A Sham Wedding:
The Wedding Banquet (1993)

You think you have problems because your aunt won’t sit next to your dad’s new girlfriend, or your uncle refuses to come because you invited your cousin’s ex-boyfriend?  Try seeing how you handle the seating charts for when Taiwanese parents unexpectedly show up to be part of your fake wedding to a woman who’s a complete stranger, while your gay lover stands around in agonizing fury.  Directed by Ang Lee, and set in New York, the movie features one of the best wedding party scenes ever—complete with a round of wedding toasts that will make you join AA just from watching.  A lush, vibrant spectacle of love, family, The Wedding Banquet offers an exploration of the meaning of commitment, in any language.


Best Movie That is Total Bullshit About Weddings And Pretty Much Everything Else:
27 Dresses (2008)


Only in some bizarre alternate universe were unicorns drive cars that fly would the idea of Katherine Heigl being the “ugly duckling” actually work. But that’s only half as laughable as the idea that Heigl would ever find skuzzy Ed Burns attractive in the first place. And speaking as a newspaper journalist, I have never ever met anyone in this profession who looks remotely like James Marsden.  If he were an actual daily news beat reporter, he’d be 30 lbs overweight, constantly nursing a steady intake of Jack Daniels and would possess all the personality and charm of a wet porcupine. And Heigl wouldn’t find him attractive either.  She would blow them both off and marry some hot Indie band singer, and then divorce him and marry some hotel billionaire.


Best Wedding Movie for People Who Hate Going to Weddings:
My Best Friend’s Wedding (1997)

Yes, yes, we know you hate weddings, marriage, engagements, flowers and basically all evidence of human happiness whatsoever. Lucky for you, so does Julia Roberts in My Best Friend’s Wedding.  In the movie that helped define “romantic comedies,” Roberts plays an amusingly vicious food writer from New York, who is shocked to learn her best friend, Dermot Mulroney, is marrying Cameron Diaz.  Wait—really?   Dermot Mulroney?  There was actually a time when we found it plausible that the two most beautiful women in the world would fight over that guy?  I’m still waiting for a more realistic sequel, where they’ve moved to Oak Lawn, she’s gained 80 lbs and they spend all their time arguing about his porn addiction; and Julia Roberts is a three-time divorcee who moved to Arizona to run John McCain’s re-election campaign.  As long as Rupert Everett shows up to sing another Dionne Warwick song, I think we could get this greenlit.


Best Family Wedding Movie:
Father of the Bride (1991)

Who didn’t want to be Kimberly Williams and have Steve Martin and Diane Keaton for parents? The original gets a nod for Elizabeth Taylor’s wedding dress, which young brides still ask for replicas of today, but the 1991 remake lands hits a nerve thanks to Martin, and his comically pained performance of a dad struggling to let go. Martin bungles his way through the planning, overwhelmed as he tries to give his daughter the best, (and cheapest) wedding possible.   Even if you hate wedding movies, period, it’s worth watching just for Martin Short as “Franck,” wedding planner extraordinaire.


Best Behind the Scenes Wedding Movie:
The Wedding Singer (1998)

It’s the movie that dared to ask about the lives of those who work to make our weddings perfect.  Adam Sandler, an all too proud wedding singer and true believer in eternal love, finds himself dumped days before his own nuptials.  Sandler earned a new crop of fans, as his endearing closeness with Drew “Julia Gulia” Barrymore proved even more heartbreaking than the demise of his own wedding.  Yes, we love it for the ridiculous hair, music and costumes that both celebrated and poked fun at the “Me” decade, but for its glimpse into the all to real lives of those for whom “that special day” is just another paycheck.


Best Movie About The Friends You Force To Come To Your Wedding:
Four Weddings and a Funeral (1994)

If you haven’t seen this 1994 film with Hugh Grant and Andie MacDowell, then your soul is empty and you are probably too dead inside to even care.  A movie that made romantic comedies less about cheesy soundtracks and clumsy heroines (see: every Sandra Bullock movie ever), it also reminded us that yes, British people are kind of funny, even the ones who don’t have bad teeth.  A great film for those of us who don’t think true love and marriage necessarily go hand in hand, but still like weddings for the free food, booze and opportunities to mock people who are happier than us.


Best Movie About Trying To Propose:
Meet The Parents (2000)

Forget everything that came after this utterly perfect comedy, so it doesn’t distract you from remembering just how funny Ben Stiller is in his attempt to propose to the girl of his dreams.  Navigating around Robert De Niro’s brutal scrutiny is enough to make any man go mad, and Stiller does so with effortless schtick. Although this movie pales in comparison to the time I introduced a boyfriend to my mother and she proceeded to tell him about the time when I was six and I declared myself “Lady No Pants” in the middle of the mall, and spent the afternoon running half-naked around the food court. I think he wanted to kill himself, too.


Best Wedding Movie for Men:
Wedding Crashers (2005)

This is the movie that made weddings fun for men.   Who didn’t want to join Vince Vaughn and Owen Wilson for a noisy rendition of “Shout”?  From Isla Fisher’s batshitcrazy pitch-perfect performance of a “stage five clinger”, to Jane Seymour as a sexed up cougar to Christopher Walken as…well, as what Christopher always is, the Cleary family could always be counted on to plunge the unsuspecting into hilariously awkward moments Who wouldn’t want to marry into that clan? More than just a bawdy romp filled with smart dialogue and some of the best lines in recent movie history, it’s also a surprisingly poignant look at just what happens when the party is over. And Bradley Cooper is in this. ‘Nuff said.


Best Fairy Tale Wedding Movie:
The Princess Bride (1987)

“Once upon a time, in a land far, far away….” It’s the line that propelled dreams of little girls for hundreds of years, until Rob Reiner turned the fairy tale romance on its end, giving audiences a witty, legendary film.  Farm girl Buttercup loses her one true love, Wesley, to the Dread Pirate Roberts, and turns to Prince Humperdinck.  On the eve her “fairy tale” wedding to the prince, everything changes. With some of the most memorable moments in movie history (“You killed my father. Prepare to die.”), it earned its place on this list long, long ago, in a land far, far away.  Also, I dare any girl to honestly admit she doesn’t swoon when she hears the words “As you wish…”


Best Movie For The Longshots:
My Big Fat Greek Wedding (2002)

It made like 800 gajillion dollars at the box office, and for that feat alone, this film deserves a mention. Let’s face it, there’s enough Cameron Diazs and Elizabeth Taylors and Malin Ackermans getting swept of their feet for the perfect wedding.  Of course the guy is going to fall for Katherine Heigle, because DUH.  But what about the rest of us schlubs? Who wants to sweep the girl who looks like Rasputin when she crawls out of bed off of her feet?  Enter My Big Fat Greek Wedding, the wedding movie for the 99 percent.

Watching Nia Vardalos get swept off her feet by John Corbett makes up for the unnecessary caricatures in the family scenes of this film (there’s a good reason the TV series based on the show bombed). Every ugly duckling can relate to Vardalos’ nervous fumblings around the tall, dreamy-eyed Corbett, and their scenes are all too real, especially as she tries to introduce him to her family. Her attempt to make her own life, away from the smothering, but well-meaning, love of her family is absolutely heart wrenching.

But, no, mostly watch it for the Corbett.