First up, full disclosure: I don’t currently have a boyfriend.
This is why I think I have waited until this golden, shining singleton moment to confess that I have never failed to have a thing for the quirky sidekick of the leading men in my life. It’s a little tricky (not to mention risky) to write this post when you’re in a relationship.
Of course I have never acted on these crushes over the years. In reality, no matter how deliciously understanding, cute, sweet and funny your boyfriend’s best friend is, the true reason for his appeal is that he is similar to your boyfriend but you don’t have to deal with his annoying habits. You get to hold onto the fantasy that he is like your boyfriend, but without the stuff that makes you grind your teeth at night. You know, those things that your boyfriend says or does that you try to ‘work’ through, but are really concerned are giving you a stomach ulcer due to all of your repressed anger and frustration.
However, it’s an entirely different situation in movies. The quirky boy best friends are exceptionally awesome and, quite often, are shunned by the girl even when they prove they are far more worthy than the leading man.
So without further ado, here is my tribute to the unsung heroes of film: the guys on the sidelines who I firmly believe should have been chosen over the guy saying, “Sorry, just realised I have been a complete tosser this whole time, but I love you. Lucky you. Will you marry me?” at the end of the movie.
1. Classic Jon Cryer. How can you turn down a young man named Ducky? He sang to you, Ringwald, he sang to you. And side note, I don’t know, I just don’t think that dress is quite… there yet.

John Krasinski, Something Borrowed.
2. Are you kidding me, Ginnifer?? What kind of name is Ginnifer? Ginnifer is the Molly Ringwald of the present day, I’ve just decided. Nothing like a close, loyal, smart, funny friend who you love dearly and is JOHN KRASINSKI, the nicest guy on the planet after Steve Carrell, when you can try to be with a guy who fell for your ditzy, self-absorbed ‘best friend’ and isn’t sure a relationship with you looks right.

Jason Biggs, My Best Friend’s Girl.
3. I refer to My Best Friend’s Girl yet again. This movie contains so many ‘what the f*@#!’ moments for me. Sure, the pie guy comes on a little strong in this one but if we’re holding him up against Dane La Douche Cook? Neither guy wins on the names though. Tank and Dusty? Sounds like an ill-written children’s book about a couple of scrappy mutts comically awaiting adoption at the local pound, lest they be sent to doggy heaven. Alec Baldwin should have been called Rover. But hey, at least Kate Hudson’s character was named after Joan Collins in Dynasty. Ok, I’ll stop it on the name criticism. But seriously, Hollywood.

Jason Lee, Chasing Amy.
4. Banky Edwards. Now I’m not saying Alyssa Jones had a shot with him (due to his predilection for dick and fart jokes), but maybe I would have taken a moment’s pause to consider the uh, offer in that living room scene at the end. Grown men who can pull off a backwards baseball cap are my weakness. Very few can. Many try.

Mark Ruffalo, Rumor Has It.
5. Ok, Jennifer Aniston, really try to concentrate this time. Mark Ruffalo or Kevin Costner? NO, GODDAMNIT! … Ok. I’m sorry. I’m going to ask you one last time. Ok. Maark, as in the handsome guy who rocked Meg Ryan’s world in In the Cut, or Kevin? Now remember, Kevin was in Waterworld. And you thought he was your father. Thank god she gets it right in the end at least.

Ed Norton, Fight Club.
6. This one isn’t entirely valid because well, 14-year-old spoiler alert, Helena Bonham Carter did actually choose Ed Norton, but to my mind, Ed is the sexier version of Brad Pitt, not the other way around as it is presented to us. Like if they were really separate people, I would be all about Ed.

Ed Norton, Keeping the Faith.
7. Ed Norton, part two. Keeping the Faith – why doesn’t Dharma, I mean Jenna Elfman, pick Ed over Ben Stiller? Given Ed directed this movie, I’m guessing it’s because he’s humble. Which makes me love him even more.

Adam Goldberg, How to Lose a Guy in 10 Days.
8. Adam Goldberg. His character is witty, articulate and gets the leading man to see reason about the lady in the end, before she gets away. Just imagine Adam on the motorbike to the tune of the best Gin Blossoms song in the movie’s finale, instead of the guy who communicates via a series of grunts, squeals and chin thrusts. Best line from McConaughey in the movie: “Naw, naw, naw, naw, naw, come oon, man, hoooooooo!” Use your words, Matthew.

Ron Livingston, Buying the Cow.
9. Three words, Bridgette Wilson: spoilt for choice. Your boyfriend’s friends include Ryan Reynolds and Ron (slacker has never been made more sexy) Livingston and you’ve gone with the crybaby who couldn’t cross a bridge in Stand by Me. And you’re a smoking hot blonde. I may also be looking at you, Rebecca Romijn. Not going to rub it in though, Bridgette, you paid the price for your mistake. We’ve all been there.

Jon Favreau, The Break Up.
10. Putting this one out there… Jon Favreau. He’s got that big bear thing like Javier Bardem that makes me just wanna sit on his lap. No, just me? Ok, never mind. I also don’t have dreams about Pete Hornberger from 30 Rock taking me out to a dive bar for beers and under-the-table knee rubs. Really, I don’t.
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- Things I Love 16: The Number of Candles on Molly Ringwald’s Cake in That 80 (oneragamuffin.wordpress.com)
- 20 Essential Molly Ringwald Moments (buzzfeed.com)
- Friday Flick – Pretty in Pink (thedomesticpeach.com)
- Go away Duckie! (forgetyesterdaylivetoday.wordpress.com)
- Pitt Back as Tyler Durden? Chuck Palahniuk Writing ‘Fight Club’ Sequel (contactmusic.com)
I’m surprised how few of these movies I’ve actually watched. I think How to Lose a Guy in 10 Days and Fight Club were the only ones. Hopefully, knowing who Molly Ringwald is redeems me.