I know the phrase "rom-com" is often treated like a sexually transmitted disease, but not all films about romance are awful. In fact that are some absolutely incredible ones. And while I was really tempted to include some anti-love stories like The Graduate, Blue Valentine or Marriage Story - I tried to stick to things you could actually enjoy with your significant other as an alternative to the same old insufferable Nicholas Sparks / Reese Witherspoon movies.
#10. The Wedding Singer
I know it's becoming increasingly easier to write off Adam Sandler with each passing Netflix atrocity, but his glory days were truly something special. And while we all knew he could make us laugh from his time on SNL, The Wedding Singer was the first glimpse at Sandler's dramatic side. His role as the dejected groom left at the alter having to relive his misery every weekend as a Wedding Singer is a hysterical meltdown of epic proportions. And his chemistry here with Drew Barrymore is a hopeless romantic match made in romantic comedy heaven. Just avoid their attempts to recapture it in 50 First Dates or Blended...
#9. (500) Days of Summer
It's hard to come up with a better millennial power couple than Zooey Deschanel and Joseph Gordon Levitt. Which of course makes it all the more frustrating to see Deschanel's Summer so withdrawn from Levitt's head over heels infatuation. But that's what makes this more than just your typical love story, it examines what exactly is missing from Tom's life that makes him so desperately in need of someone to complete him. It's an all encompassing examination of falling in love from the honeymoon stage to knowing how to pull yourself together and move on when things don't work out.
#8. The Shape of Water
Guillermo Del Toro's Oscar winning fable about a deaf janitor swooning over a fish man held in captivity doesn't sound all that romantic on the surface but its' story of acceptance and compassion is endearingly beautiful at every unexpected turn. An incredibly moving script, stunning visuals and a charismatic ensemble cast make this the most heart warming love letter to the Universal monster movies of yesteryear that you never knew you needed.
#7. Knocked Up
Seth Rogen has one hell of an on screen dating record. But he's never made a better romantic comedy than his first starring role, 2007's Knocked Up. An unexpected pregnancy depicted from the perspective of both the care free slacker and the up tight career woman makes for a hilarious modern day romance with a little more realistic circumstances than a chance encounter with your soul mate where everyone lives happily ever after. Toss in the subplot with Paul Rudd and Leslie Mann as the veteran married couple that nearly steals the show and you've got Judd Apatow operating at his absolute best.
#6. Annie Hall
No one has dissected the topic of romance more thoroughly in the modern era of cinema than Woody Allen. And he's never done it more skillfully than his Best Picture winner Annie Hall. Allen himself plays the role of the hopelessly insecure and neurotic comedian brilliantly (imagine Larry David in the 70's without all the bald jokes) while Diane Keaton's playful innocence balances their dynamic absolutely perfectly. It may be the oldest film on the list but the incredibly well crafted relationship at the center of the story makes it feel utterly timeless.
#5. Edward Scissorhands
Back before Tim Burton was more than a section of merchandise at Hot Topic, he actually made some incredible films. Edward Scissorhands perhaps being one of the finest examples of his ability to tell emotional, human stories with his unique brand of gothic fantasy. It's a heart breakingly tragic fairy tale anchored by incredible performances from Johnny Depp and Winona Ryder, another amazing score from Danny Elfman and spectacular vision from a director at his peak creativity.
#4. Eternal Sunshine of the Spotless Mind
Charlie Kaufman's work can be a tad depressing for some (I'm as morose as they come and I couldn't even make it through Synecdoche New York) but paired with the imaginative directorial effort of Michel Gondry, the taxing emotional journey here carries enough of a light hearted low-fantasy adventure feel to make all the heartache worth it. Which is why Eternal Sunshine is such a pitch perfect love story. Having such an ugly and realistic portrayal of a deteriorating relationship framed by the unique narrative structure of traveling through Joel's memories as they're erased one by one makes reliving the history of a broken heart somehow fun instead of emotionally draining.
#3. The Rules of Attraction
American Psycho author Bret Easton Ellis brings his pitch black social commentary to the world of romance in a web of entangled relationships and drugged out college kids. It's one of the most criminally underrated films of the 2000's and James Van Der Beek's sociopathic performance as Sean Bateman (Patrick Bateman's little brother) should have absolutely made him a movie star. It's the most pessimistic entry on the list by far but its' lingering question, "how well do you really ever know someone?", makes for a fascinating character study of mixed motives and altered perceptions.
#2. Before Sunrise / Before Sunset / Before Midnight
Rather than eat up a third of this list ranking each film in this series, I'm taking the coward's way out and just listing the entire Before Trilogy as one entry. If you have to know, Sunset is my personal favorite but all three are incredible films. The free flowing conversations feel so genuine that even though the series is built around a one night chance encounter, the entire thing feels more authentic than just about any relationship in cinematic history. The characters are so well crafted and their dialogue so well nuanced that writer/director Richard Linklater makes it nearly impossible not to fall in love with these vulnerable and relate-able leads.
#1. Punch Drunk Love
PT Anderson's underappreciated masterpiece about love and insecurity is my absolute favorite romance film ever made. The offbeat humor, the outstanding performances from Adam Sandler and Phillip Seymour Hoffman, the ethereal melodic soundtrack and the breathtaking cinematography make this one of the most beautiful films you'll ever see in almost every capacity. And while it's no Uncut Gems, Punch Drunk Love's 90 minute runtime keeps things quick and breezy for a filmmaker notorious for his 3 hour epics. Barry Egan's story moves at a manic pace with a raw nerve impulsiveness that makes it all too easy to get swept up in the intoxicating chaos that is falling in love.
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