Film, Pop Culture

Another 7 Indie Valentine’s Day Movies You Should Watch

Yesterday I posted my top 8 favorite indie romantic comedies/dramas for Valentine’s Day. The truth is the list started out as 12, then got chiseled down to 10, then down to 8. Sometimes I get tired of writing a post. Sometimes I look at my post and I resent it and I don’t want to write it anymore and I want to whisper how much I hate it into it’s ear if it had an ear. That’s how a list goes from 12 down to 8.

However, yesterday’s list did not accurately relay my favorite indie romcoms and romdras and so many wonderful readers pointed out quintessential films that I missed entirely. I wanted to continue the list with Another Top 7 Indie Romantic Films That I Got Too Exhausted to Talk About in Yesterday’s Post.

And, yes I know some of these movies aren’t actually indies. Like I mentioned yesterday, “indie” is the code word for “hipster”. I just didn’t want to overuse the word “hipster” this week (though it’s used maybe nine 900 hundred times in this post).


1.) Say Anything (1989)
Yes, this movie should have really been number one yesterday. This movie gives hope to nerdy, angst-riddled young men with penchants for long raincoats that they will one day get the girl of their dreams. Lloyd Dobbler is the guy that every girl wants. The truth is, every girl has had a Lloyd Dobbler or two in their life and they didn’t want him. It’s much better to fantasize about the fictional Lloyd Dobbler that we confuse for John Cusack. Lloyd Dobbler loooooves valedictorian Diane Court. Like wants to have her babies love. Everyone tells Lloyd that Diane is out of his league, but Lloyd being the confident dude that he is, asks her out. Low and behold Diane says yes and though they have absolutely nothing in common, a relationship ensues. However, like any good three-act structure, an obstacle develops in the way of their ever-lasting love. You see, Diane Court is a winner. She’s going on to become a very successful but completely alienating and unrelatable career professional. And Lloyd, Lloyd likes kickboxing! Pshaw. Oh, and he doesn’t want to make, buy or sell anything processed for a living. Get with the times, Lloyd! Diane’s Dad tells her to drop that loser martial arts tard-o and focus on becoming the next ice queen. They break up and something propels Lloyd to hold a heavy boom box over his head (something he’d probably never want to make, buy or sell). It isn’t until Diane finds out that her beloved father is stealing from the old people that he takes care of that she goes running back into the arms of Lloyd. It always boils down to daddy. The movie ends with Lloyd and Diane flying off to Europe together as Diane begins her freshman year at some fancy-ass school. If the film continued after this point, we’d discover that Lloyd and Diane quickly break-up- like most high school sweethearts do- and Lloyd is left to doing kick-boxing tricks on the Paris street corners for dough and Diane goes on to become a successful boom box manufacturer.

2.) 500 Days of Summer (2009)
Gosh, I barely remember a thing about this movie, other than that I liked it….and….there was a lot of Smiths-referencing? I guess any movie that stars Zooey Deschanel is deemed “hipstery” whether they want it to or not. She optimizes what every “young, male creative urbanite” fantasizes about- she dresses like she’s in Mad Men, she”sings” in real life, and she has piercing blue eyes under a canopy of rich brown hair. If I recall correctly, the movie centers around Tom (Joseph Gordon-Levitt) and Summer (Deschanel). They both work at a greeting card company. Tom develops a huge crush on Summer and the two start hanging out. How am I doing so far? Their friendship turns into a relationship, but it is apparent that the two have different views on love and life. They do a lot of hipstery things together like watch The Graduate and contemplate life and sing karaoke. One day they break up and Tom goes into a deep depression. Is this right so far? After running into Summer at a wedding, Tom discovers that she is engaged to another man. This puts Tom into a deeper depression, but catapults him into taking charge of his life. He runs into Summer one more time who explains to him that she now believes in love, but the love she needed wasn’t with Tom. Tom goes on a job interview and meets a girl named “Autumn”. Uh, duh. Brilliant! 500 Days of Summer is a very simple, but sweet love story that many young people can relate to. Wait a minute, who am I kidding? Who the f actually works at a greeting card company?

3.) Garden State (2004) (recommended by William Trinity, Melanie’s Randomness, Trina Estrada, Carissa McAtee)
This film came out right when I moved to Los Angeles. I saw the trailer and was like, “Oh my God, I’m Zach Braff. Big schnoz and all!” I was a big fan of this film due to my instantaneous feeling of disconnect from my friends and family back in NY upon moving to LA. I was a tool. Written, directed, and starring Zach Braff, Garden State follows the story of actor Andrew Largeman who returns to his hometown in New Jersey to attend his paraplegic mother’s funeral. While home, Andrew reunites with old friends who haven’t gone much of anywhere since high school. He also meets a young woman by the name of Sam, played by another adorable hipster idol, Natalie Portman. Sam is a pathological liar and she wear headphones all the time so you know she’s cool. Andrew spends a few days home learning more about himself, weening off of anti-depressants, and rebuilding a relationship with his father who blamed Andrew for his mother’s paralysis. Just as Andrew and Sam really get to digging each other, it’s time for Andrew to go back. Sam tearfully says goodbye to Andrew at the airport, but does Andrew actually get on the plane? I’m not going to tell you because I’ve done a pretty awesome job of spoiling lots of movies for you with these posts. Garden State is known for having a kick-ass soundtrack and making millions of people respect Zach Braff- even if it was for 5 minutes.

4.) Singles (1992) (recommended by Chelsea at Bella Vogue)
Another classic by the king of movies about young, alternative love- Cameron Crowe. Singles takes place during the height of the grunge movement in early 90’s Seattle. We follow the love lives of five people- urban planner Steve (Campbell Scott), environmental lobbyist associate Linda (Kyra Sedgwick), narcissistic musician Cliff (Matt Dillion), clueless waitress Janet (Bridget Fonda), and desperate ad exec Debbie (Sheila Kelley). Steve and Linda fall in love, but do everything possible to make it not work out of fear. The innocent Janet is in love with Cliff, but Cliff wants to keep his options open. Debbie is creepy. She makes really weird personal ad videos to try and land herself a boyfriend. They all fumble blindly through the tunnel of love as they try and figure out what they want out of life and relationships. The great thing about Singles is that though it takes place almost 20 years ago and the outfits may be a little different, young people can still relate to the characters fear of commitment and settling down. Another wonderful aspect of the movie is the absolutely adorable Campbell Scott (son of George C. Scott) who I wish could have stayed 30-looking forever.

5.) Reality Bites (1994) (Recommended by Inflammatory Writ)
I forget this movie takes place in Houston. I bet you did too. Nothing about this early 90’s alt-romcom says Texas. In fact, most people think it takes place in the same city as Singles (Seattle). The even weirder part of this movie? It’s directed by Ben Stiller. Yeah. I know! Like when he was still kind of cool. If Singles is the story of late 20 twenty-something professionals trying to find love, then Reality Bites is about their slightly younger, aimless counterparts. Reality Bites follows the love sandwich of Lelaina (Winona Ryder), Troy (Ethan Hawke), and Michael (Ben Stiller). Oh, also their is an a la carte story of Janeane Garofalo worrying that she has AIDs. Lelaina and Troy are bff and self-centered artsy types, but we all know that self-centered artsy types can never work out. They’d be constantly trying to outdo one another with their big ideas that go nowhere. Lelaina meets Michael who has his shit together. Of course Lelaina doesn’t really like dudes who have their shit together. Sounds familiar. Drama ensues all while Janeane Garofalo tries spewing her sarcastic and witty observations upon everyone. In the end, Lelaina must chose between the sweet and successful Michael and the loser musician Troy. Hmmm…I wonder who she’s going to pick? Side note- some of Reality Bites was shot in Austin and the screenwriter was 25 when the movie got made. Bitch.

6.) Lars and the Real Girl (2007) (Recommended by Tag Brum)
I think this movie is due for a second viewing. I liked it, but I didn’t love it. However, I recall the film having a very long scene where most of the live version of Talking Heads’ ‘This Must be the Place (Naive Melody)’ played and that makes ANYTHING ok in my book. Everyone knows that the live version is better than the studio version. It had ‘Genius of Love’ by Tom Tom Club too. Oh, and it also stars Ryan Gosling and even though he looks like circa 1975 pedophile, he’s still irresistible in my eyes. Lars and the Real Girl follows the story of an emotionally unstable man who dresses like a lumberjack and his love for a blow-up doll. You see, Lars has trouble relating to humans and he truly believes his blow-up doll, Bianca, is real. Unfortunately, she doesn’t look anything like Bianca Jagger which would have made the movie even cooler. Lars takes Bianca with him everywhere and his family is forced to treat her as though she’s real as well. Lars’ equally “off” co-worker, Margo, has a crush on him, but he’s too clueless to realize that. After a whirlwind romance with Bianca, Lars eventually lets her “die”. At Bianca’s funeral, Lars and Margo walk off together insinuating that one day they may have weirdo babies just like themselves. Lars and the Real Girl is a dark and slow romantic comedy-drama written by one of the writers of Six Feet Under. Though the film may be unrelatable in that we’ve never fallen in love with a plastic doll, it shows us what can happen if we go off our rocker and how our family should prepare for it.

7.) Secretary (2002) (Chris Hoffman)
Secretary is in my top 10 movies of all time, but for purposes of romance, it gets pushed down this list. This movie is definitely an atypical love story. The romance doesn’t really kick in until the end. Up until then it’s a completely degrading and depressing roller coaster of emotion. This film stars Maggie Gyllenhaal and James Spader right before he got fat. Lee (Gyllenhaal) is just released from rehab for cutting herself. She gets a job working as the secretary to weirdo lawyer E. Edward Grey (Spader). Lee is passive and weak- everything Grey secretly loves to hate. They begin a master & servant sort of relationship and Lee deludes herself into thinking that he cares for her. As Lee’s life begins to spiral out of control due to her father’s drinking, Lee looks to Grey for support. He fires her, she proclaims her love for him, he tests her by telling her to sit at his desk FOREVER. Being the good little masochist that she is, she does. Her family and pseudo-boyfriend Peter (Jeremy Davies) try to save her, but she remains still. After a few days, Grey is like, “Well, shit. I guess I have to marry this chick now”, and takes her home and treats her nicely. The end. Interesting side note- the short story that this is based on is NOTHING like the movie. No happy endings. In fact, the story ends with the secretary being fired and months down the road someone knocking on her door asking about her experiences with her former boss. Come to find out he’s running as an elected official and they want some dirt on him. Secretary the film is actually quite a beautiful love story, with one of the best character developments I’ve seen in a film. If you haven’t seen it, go rent it. It’s actually not that raunchy and focuses more on the cerebral aspect of of domineering/passive relationship.

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  • Reply Trina February 11, 2011 at 4:35 pm

    You pretty much nailed 500 Days of Summer. That has been the only movie I've ever wanted to punch a Zooey Deschanel character for breaking & puking on Tom's heart. Great soundtrack, too!

    You've given me a great list of movies I must watch this weekend! Awesomesauce.

  • Reply William Trinity February 11, 2011 at 4:43 pm

    Ahhh… Garden State, now all is right in the world.

    500 Days of Summer is amazing. If you don't remember much about it, I highly suggest watching again. It's brilliantly written and directed. It's definitely the best film made so far that explores the modern day "friends with benefits" relationship.

  • Reply Hipstercrite February 11, 2011 at 4:49 pm

    @Trina- Hey! Just linked your blog to your name in my post. I couldn't find it before! I remember really like 500 Days of Summer. I guess I should rent it again.

    @William- I remember when it came to SXSW and there was all this buzz. I recall it being a good movie. The sort of movie I wish I wrote, dammit. Argh.

  • Reply Sammy V February 11, 2011 at 5:07 pm

    Great additions. 500 Days was incredible and Garden State made me fall in love with Natalie Portman and The Shins simultaneously…

    Again, I wish Once had mad the list, it is deserving.

  • Reply Hipstercrite February 11, 2011 at 5:09 pm

    @Sammy V- I have a secret to admit- I've never seen Once 🙁 That's why I didn't write about it.

  • Reply Lauramc February 11, 2011 at 5:25 pm

    I forgot about another movie that I love and that you should love too, if you don't already. Playing by Heart is one of my very favorite movies of all time. It's one of the best performances I've ever seen from Angelina Jolie.
    Oh, you're list is pretty great.

  • Reply Hipstercrite February 11, 2011 at 5:32 pm

    @Lauramc- I remember that movie when I was going through my X-file craze. Yes, everyone was good in that movie. I liked how LA it was too. I need to watch that again. Thanks for reminding me!

  • Reply Lavina February 11, 2011 at 5:47 pm

    oh Singles! good one . Best movie/soundtrack ever! I always wanted to live in that apt. building 🙂

  • Reply Hipstercrite February 11, 2011 at 6:45 pm

    @Lavina- I know! That apartment complex kind of reminds me of Melrose Place but not as crazy.

  • Reply Lavina February 11, 2011 at 6:49 pm

    haha…..not as crazy and filled with cute Sub Pop records musicians 🙂 ahhhh if i were only born 5-7 years earlier

  • Reply Rahul February 11, 2011 at 6:55 pm

    I liked Garden State because it nailed going back to Jersey after living in LA.

    No one ever leaves. Suburbia USA.

    Then I liked Garden State more because Andrew was dead the whole time.

    Oh, spoiler alert.

    And Largeman. hehe. giggle.

  • Reply Megalithic Rick February 11, 2011 at 7:29 pm

    Singles! Yes!! Totally didn't even think about it. Reality Bits, for some reason I've never seen it, that and Say Anything. Actually, alot of these movies I haven't seen yet. I'm more of a sci-fi guy vs romance flick kinda guy. I still think Harold and Maude should be in this list 🙂

  • Reply chris February 11, 2011 at 7:30 pm

    Thanks for the shout out, Lauren. I've added this to my weekend viewing queue.

  • Reply Megalithic Rick February 11, 2011 at 7:32 pm

    Oops, I didn't see the first V-day movie post. Harold and Maude is one on that list 😀

  • Reply Skinny Dip February 11, 2011 at 7:37 pm

    Garden State, Reality Bites, SINGLES (!!!) are some of my favorite movies period. I love movies about odd balls in love.

    I really like Lars & the Real Girl. I thought it was actually a really sweet story. I'm not going to lie – I kind of teared up a bit when Bianca "died".

  • Reply Hipstercrite February 11, 2011 at 9:11 pm

    @Lavina- I wish I was 20 in 1985 Los Angeles. However, that would make me 46 now.

    @Rahul- Where in NJ?

    @Rick- What's your favorite romantic sci-fi movie? 😉

    @Chris- And I'm going to watch Secretary this weekend! Just thinking about it made me excited to watch it again!

    @Skinny Dip- Gosh, I really do need to watch that movie again. Gosling is such a good actor.

  • Reply Emily Ann February 11, 2011 at 9:45 pm

    (500) days of summer is one of my favorite movies still. It makes me a little heart sick and want to do a little musical number to hall and oats on my way to work some day.

    Check out Once though – it's a little depressing but you'll be doing shitty accents for awhile after it.

    Did you consider That Thing You Do? (okay it's not all that indie/hipster) but still great love story between Faye and Guy. Not to mention who doesn't love the One-ders 🙂

    Overall freaking love these choices – particularly Say Anything too. Its where my crush on John Cusack began….

  • Reply The Kid In The Front Row February 12, 2011 at 1:37 am

    Great choices!

  • Reply chariskalee February 13, 2011 at 3:41 pm

    So I love and have seen all of these movies. I think that makes me a hispter by default 😉

  • Reply William February 13, 2011 at 3:58 pm

    I love this list, it has most of my favourites, and a couple new one movies to check out. thanks!

  • Reply . February 14, 2011 at 4:07 pm

    I love that chose Lars and the Real Girl, it's such a greeaat movie and kind of a low flyer. Ohh, and I'm jazzed you chose Harold and Maude for your last post, that movie is perfect.

    John E. Sullivan

  • Reply Jennifer February 12, 2012 at 4:31 pm

    I love movies lists where I have actually seen all the movies – and they are all great. I may go back and re-watch a few. Except maybe Reality Bites and Singles because they just make me feel to old

  • Reply icyhighs February 13, 2012 at 1:17 pm

    Great list!
    I’d like to add : Chasing Amy, If Lucy Fell, LA Story.

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