
It starts as a tongue-in-cheek fairytale romance, so you're comfortable with how predictable the plot and how many coincidences might happen for the boy to meet the girl; just like last year's multi-Oscar winning "Slumdog Millionaire".
It's not a breakthrough of a romantic comedy, but it has enough unique elements that make it stand out from some random romcom with more famous actors. There is the back-and-forth between the actual 500 days so the chronology is mixed around to paint a picture of what happened between the boy and girl before and after they separated for a while. The back-and-forth makes the witty script shine, so clearly there was some thought to the plot structure even though most of it is predictable.
The setting of this character drama is, the boy works at a greeting card company but actually wants to become an architect. There is some biting commentary on greeting cards which was funny and truthful; when the boy is in the dumps, his boss tells him to channel his negative energy into funeral/sympathy cards!
The architect side of him is never really explored, and is only given a nice moment where he draws his version of the city on the girl's arm as a tattoo. There's no payoff to that, sadly.
The girl (Zooey Deschanel) is a unique character in herself. She's pretty much a goth, but she is commitment phobic. She doesn't believe in love, he does. The girl and boy in this film are actually more experienced in that they've been through past relationships, which is something I haven't seen in many romantic comedies. Why they break up for a while never is made clear though, or at least what event that triggered it. What eventually builds up to the ending is actually intriguing, because it's as if the fairytale Disney story grows up and becomes a sobering message. I thought it was really cool that even if the boy and girl can have exact same tastes in music, movies, and other things, that don't mean they're "soul-mates" or they're meant to be together. Relationships aren't built on such superficial circumstances, contrary to what online and other matchmaking services might have you believe
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The supporting characters are really what sells the experience, and give some of the funniest moments. The character who steals the show is the boy's much younger sister (about 9-10 yrs old) who is a love guru to him.

She even mentions that she has past boyfriends, which is hilarious for such a young girl
She's going to be in the Kick-Ass comic adaptation, which is looking awesome.

It's a pretty funny film, and the interplay between Gordon Levitt and Zooey is fantastic (
even though Zooey's eyes are creepy). One hilarious moment is, when the couple is in Ikea and they do some role-play with the furniture. They go from the kitchen to then the bedroom, but before they get intimate, the boy breaks the ice by proclaiming, "I dunno, but there's a Chinese family in our bathroom…". That made me LOL hard. Another hilarious scene is when the boy goes to the movies and you see a parody of French new-wave artsy b+w movies. "Suffering...so much suffering" made me LOL hard again, and you'll too once you see it. Zooey does a serviceable job, but this movie is more about the coming-of-age for the boy and how excellent Gordon Levitt is as the next big Oscar actor. What might make for a somewhat melodramatic plot ends up in a really excellent ending that really speaks more to the title of the movie. It plays more to random coincidences in life that can be fruitful, rather than the fairytale romance that the movie starts with, which I thought was a great tonal shift to end on.
The reason I won't say that this is an amazing or original romantic comedy is, you don't really get to delve into the psychology of these characters. It delves more into the relationship and the 500 days, but then you realize there is not some huge mystery to it or any big plot twist. There are some loose ends like the boy's architecture drawing on her arm. The plot becomes victim to its fairytale premise by being melodramatic (she was that angry about him punching a guy who was hitting on her in the bar?!) and predictable. It's also not the most memorable thing ever. I've always wanted some outside thinker to examine a romantic comedy or any genre, and deconstruct it. Much like what Christopher Nolan did with a crime thriller in Memento. If you do want a recent deconstructionist romcom, check out "Search for a Midnight Kiss" which pays more than enough homage to "Annie Hall". But yeah, "500 DAYS OF SUMMER" stands out as a must-watch romcom if you're annoyed by the generic romcom market saturation ("Ugly Truth"). Absolute must-watch if you're a Joseph Gordon Levitt fan like me (Brick, 3rd Rock from the Sun, Mysterious Skin).
Yes, I do watch quite a few romcoms.
Look forward to GTA IV completion impressions, and MGS 3.
Comments
1) Nice review, definitely seeing the movie
2) Get a new picture of Zooey! She is very pretty and that is just about the worst photo of her imaginable!
DoctorBedlam