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11 Movies like 500 Days of Summer: Confusing Romances

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Jane Howarth itcherFresh out of ‘not a love story’ movies?  I’ve got you covered with five romantic comedies that don’t believe true love is easy to find. ~ Jane Howarth

What Films are Like 500 Days of Summer?

It’s hard to miss the fact that 500 Days of Summer (Marc Webb, 2009) is a little different – from the first moment, it shows us Summer and Tom getting together and breaking up pretty much side by side. And as if that wasn’t enough, it flits between love and life issues.

There must be more movies like 500 Days of Summer, so what are they?
I’m pretty sure you’ll love Nick and Norah’s Infinite Playlist (Peter Sollett, 2008), Juno (Jason Reitman, 2007) and Adventureland (Greg Mottola, 2009).

But I’m also pretty sure you’ve already found them, and being an itcher devotee you’ve probably caught up with Jonny’s movies like The Perks of Being a Wallflower (Stephen Chbosky, 2012) too, right?


Now for my Personal Recommendations

They might come from the ‘90s and beyond, but if you’re looking for a borderline rom com with an introspective side, I think you’ll like these.

‘The Way We Were’ (Sydney Pollack, 1973)

Couldn’t we both win?

Two desperate people (Barbra Streisand & Robert Redford) have a wonderful romance, but their political views and convictions drive them apart.

There isn’t a dry eye in the house by the time the credits roll….This film shows that sometimes, no matter how much you might love someone, life stuff just gets in the way. And maybe, just maybe, love doesn’t conquer all!

Both movies share a focus on the internal workings of romance, just this one focuses on their differences instead of their similarities.

‘War of the Roses’ (Danny DeVito & Thomas Lofaro, 1989)

You really expect me to keep on reassuring you sexually even now when we disgust each other?

This comedy shows us just how horrible divorce can get and how interesting it can be to watch, when you are not the victim. As Oliver and Barbara’s (Michael Douglas & Kathleen Turner) flawless marriage unravels, the two grown adults are reduced to acting like children. Furniture is damaged, animals are accidentally killed, and nasty jokes are played, all in the name of taking revenge. It’s not until later that the couple recalls why they fell in love in the first place.

The lesson here; love ain’t worth it, honestly….

Both films offer great comic timing, but this one is quite a rollercoaster ride and plays out a hate/hate relationship.

‘Amour’ (Michael Haneke, 2012)

Things will go on, and then one day it will all be over.

So this movie may be able to teach us about love, but it’s in no way a fluffy love story. The French film, directed by Michael Haneke, focuses on an elderly couple and the process they go through after the wife, played by Emmanuelle Riva, suffers a series of strokes, leaving her unable to speak and paralysed. We follow George (Jean-Louis Trintignant), her husband, as he copes with what’s happened. It’s an unflinching, terrifying and artistically beautiful look at the nature of love, death and ageing.

These movies are both about making the right choices at the right time; but this one steps it up with a more sophisticated tone.

`Almost Famous´ (Cameron Crowe, 2000)

Cameron Crowe’s iconic and personal tale of hero worship, growing up and meeting people who aren’t The One.

Like 500 Days of Summer, Almost Famous proves not every relationship (or movie) is destined for a happy ever after, and it recognises that there are so many types of love and ways to show it.

It’s even got a blink-and-you’ll-miss-it Zooey Deschanel appearance.

And if you can’t get enough of life on the road? Roxanne’s compiled some great recommendations for Almost Famous fans.

The ‘70s rock backdrop makes a change, but the characters’ tangled love triangles and changing ambitions make for a very similar movie.

`High Fidelity´ (Stephen Frears, 2000)

The Chicago setting might be a little unsettling for devotees of the original London-set novel (High Fidelity (Nick Hornby, 1995)), but at its heart this movie’s pretty close to the source.

John Cusack’s Rob talks to us, narrating his life and break-up through life-themed compilations such as the ‘top five things I miss about her’.

Like 500 Days of Summer, High Fidelity is all about break-ups and finding the right one, with bonus points for the music connection.

My secret favourite thing about this movie? Jack Black’s music snob.

The break-up journal format and musical influences make High Fidelity great alternative viewing.

`The Apartment´ (Billy Wilder, 1960)

Jack Lemmon and Billy Wilder made seven films together, after realising they liked each other’s style (and so did audiences).

In The ApartmentLemmon’s likeable C. C. Baxter tries to navigate cubicle life and the small, small world of office romance.

I guess life wasn’t already complicated enough for Calvin Clifford, because he’s agreed to let his bosses use his bachelor pad as a secret hideout for meeting their mistresses.

This can’t go wrong, right?

C. C. reminds me a little of Joseph Gordon-Levitt’s Tom, a nice guy who’s not perfect, and the story?

Well, if you’re looking for an unconventional rom com, you’re in the right place.

Cubicle life and an imperfect but likeable hero aren’t the only shared qualities, this vintage movie has a pretty similar sense of humour too.

`Breakfast at Tiffany’s´ (Blake Edwards, 1961)

I’ll let Kerry tell you why it’s one of the top old movies you’ve got to watch, but what makes it the perfect 500 Days substitute?

Paul loves flighty, distant Holly, a girl he doesn’t understand and can never quite catch hold of – sounds pretty familiar.

The narrator’s slightly melancholy fascination with an unobtainable girl is familiar, but here the focus shifts to elegant visuals and drama.

`Sliding Doors´ (Peter Howitt, 1998)

Writer/director Peter Howitt’s rom com took the former actor seven years to write, and this version only made it to the screen thanks to John Hannah, who went on to co-star in it.

The final product sees Gwyneth Paltrow’s Helen missing her train in one version of events, catching it in an alternate timeline.

With its split timelines and bittersweet romances, this movie epitomises ‘expectation versus reality’.

I will never understand why short hair equals independence though (can’t a girl think for herself without a crop?), but it’s still awesome.

Sliding Doors is 500 Days viewed entirely through the expectation versus reality frame, while its clear good and bad lifestyle choices put a different spin things.


If You Like ‘500 Days of Summer’, You Will Like…

So why is falling in love such a serious business? Take a chill pill Hollywood producers and have a look at these three films like ‘500 Days of Summer,’ that show the act of love and romance as bizarre tangents and dream sequences….kind of how I see life in general really….

‘Better off Dead’ (Savage Steve Holland, 1985)

Go that way, really fast. If something gets in your way, turn.

Lane Meyer (John Cusack) is a love struck teenage boy who is hopelessly in love with Beth (Amanda Wyss). When Beth dumps him for the popular captain of the ski team, Lane’s whole day quickly goes to hell. He is bullied, beleaguered and torn apart by everyone from the paper boy, who appears to show up all over the place to the ghostly voice of a radio deejay. Lane attempts suicide in vain. His ultimate escape comes in the form of a French exchange student (Diane Franklin) who develops a long-distance crush for him.

You’ll find despairing male leads in both these films, but this one relies more on silly situations for the comedy.

‘Sleepwalk with Me’ (Mike Birbiglia, 2012)

I think falling in love for the first time is such a transcendent feeling. You know, it’s like eating pizza-flavoured ice cream your brain can’t even process that level of joy.

Exclusively a comedy? Hell no. There are some classic comedy routines that Mike (Birbiglia) is so well known for here, but really its window dressing for how his relationship, sort of stuck in neutral, begins to affect them both after so many years of no commitment. Just like life, there are some good times, bad times, and all of those times in between. I’m trying to remember the last good relationship movie I saw that so cleanly portrayed the love of two people that were really not made for each other, and didn’t know it until so many years had passed….

Both films are strong romantic comedies; this one includes some perfect chemistry and a much thicker plot.

‘Safety Not Guaranteed’ (Colin Trevorrow, 2012)

Because you gotta be sincere and charming. Okay? He’s used to assholes like me coming and making fun.

With a budget of perhaps 10 boxes of Coco Pops, this film managed to be the most entertaining thing I’d seen in a good long while. The entire cast fits together and play off each other in a delightful way and the ending is great without being sappy sweet or mushy.

The movie’s premise, about a guy who wants company for a “second attempt at time travel”, opens up some simple yet timeless human stories of longing, redemption, love and faith. Any which way that the movie had ended, whether in failure or success for the time traveller, would have been fine. Why? Well, precisely because it’s what happens in between that’s important, and cool. For Darius (Aubrey Plaza), for Jeff (Jake Johnson), for Kenneth (Mark Duplass) and a few others, the journey through time is well, that which all of us take: no need for a machine for that.

Both these films feature love in a big way; but this one offers a little more comedy to help you swallow it down.


What makes 500 Days of Summer so Great?

It’s got a rom com side, but it’s also about life and working out what you want – and of course there’s an LA setting that’s not even a little bit about Hollywood.

And if all else fails?

Make it a Joe G-L marathon with 10 Things I Hate About You (Gil Junger, 1999), because there’s never a bad time to watch it.

Anything Missing?

When I’m looking for a movie that’s equal parts about love and life, I go for these. I’m also sure you’d like these movies like ‘Away We Go’. But are there more good movies similar to 500 Days of Summer out there?

Tell us, what picks you up from the aftermath of Tom and Summer’s confusing romance?

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