Everything I Learned About Love in the '90s I Learned From Ben and Gwyn

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To honor the 15th anniversary of "Shakespeare in Love's" coup at the 1999 Oscars, Pret-a-Reporter gets nostalgic for Gwyneth Paltrow and Ben Affleck's late '90s romance and the classic movies they churned out at the end of the millennium.

This year marks the 15th anniversary of Shakespeare in Love's triumph at the Oscars, including then-26-year-old Gwyneth Paltrow's win for Best Actress. Paltrow was dating Shakespeare co-star and fellow Oscar winner Ben Affleck at the time, which has prompted Preta to reflect on the canon of films the young lovers produced in their over-achieving three-year span from 1997-1999. From the romantic delusions of Chasing Amy to the what-if whimsy of Sliding Doors, pretty much everything you need to know about relationships can be found in these '90s gems from Ben and Gwyn:  



Chasing Amy

Ben made a risky decision in this film to claim undying love for a lesbian, played by the queen of sexy baby voices, Joey Lauren Adams. Even riskier was his assumption that she had never slept with a man before him, which blew up in his heteronormative face spectacularly. Remember, Ben: to assume is to make an ass out of you and…you. But mostly this film is important for marking the end of Ben's unfortunate goatee phase, for which we are eternally grateful.


Good Will Hunting

Ben didn't have much going on romantically in this one, unless you include his bromance for the ages with Matt Damon, aka Will Hunting. But would Will have gone to see about a girl without Ben's epic "the best part of my day is when I knock on the door and you might not be there" speech? We think not. This Beantown bro was one selfless wingman.


Forces of Nature

A guilty pleasure no more, this film can now be celebrated for its brave and unlikely pairing of Ben and Bullock. Sandy B had never been as freakishly charming, nor he as adorably neurotic, as in this perfectly '90s installment of A Funny Thing Happened on the Way to the Altar.



In this classic '90s space disaster epic, Ben used Liv Tyler's stomach to prove that the only aphrodisiac you ever need is Animal Crackers. And watching that scene proved to be an aphrodisiac for every teenager in America.

Buena Vista/Giphy

The defense rests for Ben.

Sliding Doors

Who hasn't wondered what would have happened if they hadn't just missed that train? Well, thanks to Sliding Doors we'll never stop wondering. The film's exact message is still a bit unclear - just when you think this version of Gwyneth is winning over that version, this one goes and dies on you. But hey - no one ever expected the Spanish Inquisition!


Great Expectations

My high school heart goes pitter-patter remembering the nude drawing sessions between Gwyn and Eth, crazy Anne Bancroft waltzing around in her bathrobe to Besame Mucho, and a soundtrack filled with 90s stalwarts Tori Amos, Duncan Sheik and The Verve Pipe. Lesson learned? Little girls who like to torture their little boyfriends will keep at it well into adulthood. But when they look like Gwyneth in Great Expectations, the boyfriends don’t seem to mind.


A Perfect Murder

So many morals to this story, where do we even begin?  Thank you, Gwyneth, for teaching us not to marry villainous-looking men 30 years our elder, not to be careless in our affairs with hot downtown artists (especially if they resemble Viggo Mortensen), and not to take long baths unless we know who’s in the next room. What should we do?  Always ask the maid to leave the meat thermometer on the counter.  You just never know when it may come in handy.


The Talented Mr. Ripley

Sometimes our boyfriends have bad taste in friends. It happens. But when we suspect said friends of murdering our boyfriends, and then impersonating them, it’s probably best to do more than just pull out the quivering lip, as great as Gwynie is at that. Special shout-out to one of the most delicious Philip Seymour Hoffman performances ever, as Freddie, the boozy jazz snob whose bullying of Tom Ripley causes him to meet the wrong end of a blunt object.

Paramount/ http://fradine.tumblr.com/

Shakespeare in Love

At its simplest, this 1999 Best Picture Oscar winner taught us that if you don’t want your life to turn into a Shakespearean melodrama, don’t date Shakespeare. The film can also be regarded as the high-water mark of Gwyneth’s career, which is a bit shocking considering that it was 15 years ago. But what a time it was for pre-Goop Gwyn, whose luscious golden extensions and impeccable British accent helped us fall in love with the theatah all over again (or perhaps even for the first time). Harvey Weinstein has suggested a sequel may be in the works, to which we say, “It is a new day…it is a new world!


Aaaaaand...end scene.