Film, Pop Culture

Top 8 Indie Valentine’s Day Movies

Indie being a code term for “hipster”. I already used up my one allotted use of the word “hipster” this week.

Many of these films aren’t even indies, but they are just quirky enough to earn a place in the hearts of millions of pretentious young people like myself.

So, in honor of Valentine’s Day and with a little help from my friend Levi, here are the top 8 best indie/alternative/hipster romantic movies for the death-obsessing, mixtape-making, Smiths-loving couples out there.

1.) Harold and Maude (1971)
Harold and Maude chronicles quite possibly one of the most unconventional, but beautiful relationships captured in contemporary film. Directed by a dude with one of the coolest old-man name’s, Hal Ashby (Shampoo, Being There), this ground-breaking film follows the May-December romance of the young and somber Harold and the Jurassic and vivacious Maude. Harold comes from a wealthy family and he’s bored with it all… and really into death. The 1970’s goth kid came in the garb of polyester suits and turtlenecks. Everyone is obviously too dumb for Mr. I Have a Better Comb Over Than Donald Trump, until he meets the quirky 79 year-old Maude at a funeral that neither one was invited to. The two start talking and discover that though they have nothing in common, they both can offer a lot intellectually to one another. Harold falls for the old broad and plans to marry her. They bone. Maude announces that 80 is the perfect age to die. They share one lovely night together and then…oh, I’ve said too much. Harold and Maude is a classic story that continues to resonate with new audiences due to it’s championing of atypical love and the idea of living life to the fullest. And watching old people gettin’ it on.

2.) Annie Hall (1977)
No movie captures the love of two completely f’ed up 30-something narcissists like Annie Hall. Woody Allen sure knows how to take completely unlikeable people in real life and make then adorably non-punchable in the movies. Alvy Singer (Allen) meets Annie Hall (Keaton) during a really awkward game of tennis where she whips out her ol’ reliable “la-di-da’s” to win over the affection of the Jewish midget. Though the relationship starts off sweet and romantic, we watch the realities of how two people can grow apart. Unlike Blue Valentine, which makes you want to rip your heart out and then eat it in hopes of saving some part of it, Annie Hall is bittersweet but optimistic in knowing that Allen will go on to bang a lot of dames totally outside his league. Annie Hall is the sort of movie that gives faith to self-centered people that they will indeed find someone just like them one day- and then lose them.

3.) Eternal Sunshine of the Spotless Mind (2004) (Levi)
Michel Gondry finally gave the twenty-somethings a gift they never thought they’d receive. A compelling, nuanced, serious performance from our generation’s Bill Murray, Mr. Jim Carrey. And before you cry foul, riddle me this, how many times have you quoted a line from Ace Ventura, or Dumb and Dumber…that’s what I thought. But Jim Carrey’s performance in Eternal Sunshine of the Spotless Mind showed us a real character with believable grievances. Kate Winslet began the road to perfecting her near-perfect acting technique, and who the hell doesn’t like Mark Ruffalo? It’s a great love story told from a completely new perspective by chronicling the decline of a relationship in reverse, so at the beginning of the film you see how a once-loving, quirky relationship reached its breaking point. As the movie progresses you arrive at the fairy-tale, carefree happy ending… which is really the beginning…like, whoa. (the young’uns can substitute “like, whoa” with “that’s so meta” if they so choose.) In the end, I don’t recommend it as a first date movie…or a middle date movie. Watch it if you’re alone, so you remember what it’s like to be happy by dwelling on the past. That’s healthy.

4.) Edward Scissorhands (1990)
If you were born in the 1980’s, then you love this movie. Like love love. And if you don’t, then there is something inherently wrong with you and you should be taken out behind the barn. Who thought that a love story could be so heart-breaking between a young girl with a terrible dye-job and whatever the hell Edward is. Like most fairy tales, the story of Edward Scissorhands is simple- weird robot dude with scissorhands is built by Vincent Price in a castle at the end of the street, Avon lady tries to sell robot dude some lipstick, realizes he’s pretty pathetic and brings him home, his Robert Smith-demeanor charms the pants off of the young daughter much to Anthony Michael Hall’s man-boob chagrin, robot dude makes some really awesome bush and ice art and wows the neighborhood, Bitch Tits tries to mess things up for robot dude, robot dude goes into hiding, the two get into a fight, Bitch Tits dies, robot dude has to stay in hiding forever at the castle at the end of the street while Bad Dye Job swirls to Oingo Boingo as an old lady. See? Like most classic fairy tales.

5.) High Fidelity (2000)
High Fidelity is the sort of book/movie you wish you made. Everything about this movie is perfect. From the pop culture references to the wisdom of break-ups to the realities of life, this movie gives me a huge bone-bone every time I watch it. Rob Gordon is a much like the 30-somethings in Annie HallAwww….real love. What makes this movie so special is that Rob has a top song list for everything that happens in his life. It also makes legions of young hipsters want to stay perpetual losers well into their 30’s.

6.) Waitress (2007)
When this movie came out, I stayed away from it for two reasons- 1.) It had Keri Russell in it, and considering I only knew her from Felicity, I assumed it was going to be stupid ass and 2.) I thought it was a chick flick and I try to not think of myself as a chick though I really love The Notebook. What made me check out the movie was the sad fact that the writer/director/co-star of the movie, Adrienne Shelly, was murdered before the film was released. I’m so glad I gave this movie a chance because it is one of my all-time faves. Waitress follows the story of Jenna (Russell), a sweet waitress trapped in an abusive marriage and dead-end town. She disappointingly discovers that she’s pregnant and she begins telling the unborn baby how much she hates it. Que doctor Malcolm Reynolds with his smoldering good looks and Jenna finds herself intrigued by the affection of someone other than her deadbeat husband. Romance ensues, a lot of pies are made, and Keri Russell charms the living pants off of everyone.

7.) Grosse Pointe Blank (1997) (Levi)
With an impeccable soundtrack by Joe Strummer, witty inside-banter-like dialogue and a relationship that’s too cool for school, Grosse Pointe Blank became a hipster cult hit before hipsters could grow facial hair. In the film, hitman Martin Blank (John Cusack) gets invited to his 10 year high school reunion and reluctantly attends when an obligatory killing contract brings him to his home town. Blank reignites his relationship with Debi Newberry (Minnie Driver) through a flurry of “what could have been” scenes, until ultimately, the only way Blank can win his love’s trust back is by killing a whole lotta guys to protect her father – the man he was sent to kill. If anything, watch it for one of the best uses of Queen/Bowie’s “Under Pressure.”

8.) Punch-Drunk Love (2002) (Levi)
Probably one of the most underrated love stories of the past 20 years. P.T. Anderson’s take on the socially awkward and pudding collecting character Barry Egan also fulfills the casting fantasy of actually liking a performance from Adam Sandler. In fact, I felt somehow robbed of faith in Hollywood when Sandler didn’t get a nomination for best actor. But like “The Big Lebowski” before it, “Punch Drunk Love” leaves you guessing at your feelings toward the film. Was that a comedy or was I supposed to be taking that seriously.? There are parts that make me shit my pants with laughter (a date turn-off, by the way). Like when Sandler’s character tracks down Dean Trumbell, the man responsible for roughing up his love, (expertly played by Phillip Seymour Hoffman) he’s still clutching the phone receiver and cord he tore from the wall in a fit of rage from the previous scene. And their confrontation? “I’d say that’s that, mattress man.” Classic movie line. Then there are parts where you’re witnessing ooey gooey love sequences with the marvelous Emily Watson, who loves Barry even though he’s one of the strangest men on earth. Definitely not for an uneducated couple, they wouldn’t understand the nuance – then they’d complain to their local Blockbuster for giving them an unfunny Adam Sandler movie. Highly recommended for a smart, attractive couple with a regular sex life, because if you both enjoy the greatness of this film, you should probably stick together.

Honorable Mention:
-The Baxter (2005)
-Lars and the Real Girl (2007)
-So I Married an Axe Murderer (1993)
-Wild at Heart (1990)
-True Romance (1993)
-Moulin Rouge! (2001)
-Badlands (1973)
-Say Anything (1989)
-500 Days of Summer (2009)

What are your favorite indie romantic comedies/dramas? 

Previous Post Next Post

You Might Also Like


  • Reply Jessica February 10, 2011 at 6:48 pm

    been following your blog for awhile now….this list is hilarious.

  • Reply Sarah Wilks February 10, 2011 at 6:56 pm

    Brilliant list!

  • Reply Lauramc February 10, 2011 at 7:04 pm

    Phenomenal list
    I would add to it:
    Better Off Dead
    Benny and Joon

  • Reply Christine Macdonald February 10, 2011 at 7:08 pm

    Annie Hall is by far my all time favorite movie. Excellent!

  • Reply Nicole February 10, 2011 at 7:09 pm

    What about Rushmore? Hipsters like Wes Anderson, right?

  • Reply William Trinity February 10, 2011 at 7:22 pm

    Great list! But seriously, no Garden State?!?

  • Reply AVY February 10, 2011 at 7:23 pm

    Manhattan is even better than Annie Hall. I think Big Fish is sort of romantic.

  • Reply Jessica February 10, 2011 at 7:46 pm

    So happy Harold & Maude and Edward Scissorhands are on the list!

    Also on my list:
    The Nightmare Before Christmas
    Big Fish
    Roman Holiday
    The Crying Game
    Jim & Jules

  • Reply Lavina February 10, 2011 at 8:15 pm

    ahhhh Cusack, every "Indie" girls' fantasy…….so I hear.I wouldn't Know 😉

  • Reply That Chelsea Girl™ February 10, 2011 at 8:30 pm

    I have Empire Records and Singles as a double- feature DVD…I love both, as far as early-90s hipster flicks go.

  • Reply Benny February 10, 2011 at 8:33 pm

    Nice list! I'd (about to make a confession) nearly forgotten about Edward Scissorhands. Must check out Waitress and Grosse Point Blank now. I remember when Eternal Sunshine first came out, one of my friends said, "You absolutely have to watch this with whoever you're hooking up with." But I very much agree with Levi's statement that, no, you should not watch it on a date (or whatever you want to call it), ever.

    Punch-Drunk Love is definitely a great choice! It's true- if it turns out that you love it, but the other person doesn't, then your viewing of the movie will probably do a whole lot of work for you…

  • Reply inflammatory writ February 10, 2011 at 8:44 pm

    Reality Bites and Benny and Joon have to be on there!

  • Reply Melanie's Randomness February 10, 2011 at 9:04 pm

    I agree on Waitress, Edward Scissorhands, High Fidelity (LOVE), and Gross Pointe Blank. I have to see Eternal Sunshine of a Spotless mind! I liked Garden State alot. It renewed my faith in Zac Braff.

    Melanie's Randomness

  • Reply Anonymous February 10, 2011 at 10:26 pm

    Grosse Point Blank over Say Anything?

  • Reply IT (aka Ivan Toblog) February 10, 2011 at 10:35 pm

    I think I am a little disappointed that The Graduate didn't make your list.
    Then again I can't complain too much because the only one on it I saw is Harold and Maude.

  • Reply Hipstercrite February 10, 2011 at 11:13 pm

    @Jessica- Yay! Glad you liked it!

    @Sarah- Thanks! Think I'm going to do a part 2 now!

    @Lauramc- Wow. All excellent recommendations that I didn't even think of!

    @Christine- Me too! It's my number 3 of all time!!! So so so so so so so so so good.

    @Nicole- Yes, you're so right. I didn't think of it as a romantic movie, but it really is. Good suggestion!

    @William- I know, I know. Thinking of writing a part two and will add Garden State.

    @Avy- Them there are some fighting words, girl! 😉 Manhattan is good, but for romance?

    @Jessica- Oooh…good list. Thinking outside of the box! I like that Crying Game is on there!

    @Lavina- Seriously, I could probably just do a top 10 romantic movies starring John Cusack!

    @Chelsea- YES! Brilliant! Great suggestions! Haven't seen Empire Records (I know), but Singles is perfect (as I'm sure Empire Records is).

    @Benny- Levi says thank you!

    @Inflammatory Write- Oh crap! How could I forget Reality Bites? It freakin' takes place in Houston! Good one!

    @Melanie- I don't care if it's not cool to like Zach Braff, but I loooooved Garden State when it came out. I had just moved to LA so I falsely believed I could relate to it.

    @Anonymous- You're right. Say Anything is on the list for tomorrow.

    @IT- Graduate is excellent, but is it hipstery?

  • Reply carrie February 11, 2011 at 4:39 am

    ooo have you seen Peter & Vandy. saw it on instant netflix the other day. and to make it double hipster friendly, it is shot with unmentioned (at times undecernable) flashbacks, making it slightly confusing to follow at first.

    love your blog,


  • Reply Sammy V February 11, 2011 at 4:57 am

    What a hip list. Annie Hall is brilliant. I second Lauramc, Once should definitely be on the list.

  • Reply Amanda @ Hungry Vegan Traveler February 11, 2011 at 5:12 am

    LOVE "High Fidelity." One of my top 5 favorite films! 😉

  • Reply MG February 11, 2011 at 3:59 pm

    Seriously. I love all of these. Hands down, Annie Hall is my favorite. I am obsessed with Woody Allen films.

  • Reply IT (aka Ivan Toblog) February 11, 2011 at 7:49 pm

    Yer right. The Graduate was hip, but not hipstery.

  • Reply Anonymous February 13, 2011 at 5:51 pm

    Do you even know what constitutes an indie film? also… fix your layout

  • Reply chris February 9, 2012 at 5:32 pm

    Awesome list, Lauren!

    Have you seen Hal Hartley’s Trust, also has Adrienne Shelly in it. You’d dig it.

  • Reply Jennifer February 12, 2012 at 4:29 pm

    Great list – and I am once again reminded I really need to watch Annie Hall

  • Leave a Reply