Damn You, Lloyd Dobler!

If video killed the radio star then Hollywood killed the healthy relationship. It wasn’t Col Mustard in the study with the candle stick. It was Cameron Crowe in the movie theater with John Cusack. Seriously, every woman who was between the age of five and thirty-five during the late 80’s to early 90’s will forever be haunted (and taunted) by the elusive perfection of true love depicted in Say Anything. As a requiem for the perfect relationship that (thanks to the monster success of the almighty chick flick) we will never have, I give you a list of the top ten Hollywood boyfriends who have forever ruined it for all the regular guys.



#10 “Tripp” (Matthew McConaughey), Failure to Launch

Granted, the cowardly way Tripp uses living with the parents as a means of breaking up with women once they give him the dreaded “look” seemingly makes him all too disappointingly real to belong on this list. However, he has several other too-dreamy-to-be-true traits that definitely qualify him for silver unicorn status. If a man who looks like Matthew McConaughey lives at home in his thirties, it’s most likely because he’s a lazy pothead who’d rather blow his Joe’s Crab Shack paycheck on “Canadian Supergrass” than get his ass off his parents couch and get a real job. Even if the reason that he’s shacking up with mom and dad isn’t a drug or alcohol addiction, I can guarantee it’s NOT because he’s just too scared to get close to a woman again after the love of his life tragically died years ago. Also, in real life ultra good-looking dudes like Matthew M and Bradley Cooper don’t fret about their romantic relationships while they are mountain bike riding and playing basketball. In what alternate Mountain Dew meets Kotex commercial universe does this kind of stuff really happen? And how do I get there?



#9 “Jonathan Trager” (John Cusack) Serendipity

In his first appearance on this list, Mr. Cusack plays an ESPN producer haunted by a mysterious and enchanting encounter he had with a gorgeous British woman (Kate Beckinsale) eight years earlier. Armed with only his memories and the woman’s totally common first name (Sarah), Jonathan sets out on a cross-country adventure to reunite with his long-lost love. Randomly, this all occurs just days before his wedding to another woman. What man do you know who would even be thinking about some girl he spent one (sex free) night with after eight years? Let alone be willing to jeopardize his engagement, deal with the most annoying Bloomingdales employee who ever lived, and fly across the country to find some woman who for all he knows could be dead. Or having sex with some ugly blonde guy right in front of an open window when Jonathan decides to show up unannounced at Sarah’s San Francisco home (luckily for Jonathan, this woman turns out to be Sarah’s sister). The fact that Jon boy leaves his fiancée at the altar does give him some street cred, but in real life Sarah and Jonathan both would have moved on, fell in love with and gotten married to other people. Although I suppose there is the remote possibility they could have divorced their spouses, reconnected via Facebook and lived happily ever after. No Eugene Levy required.



#8 “Jamie Bennett” (Colin Firth) Love Actually

Everything about this man is straight out of a Jane Austen novel, right down to his charming, perfectly posh name. I suppose it is fitting since Colin Firth is the quintessential Mr. Darcy, a role he played to perfection in both Pride and Prejudice and Bridget Jones’s Diary. When Jamie retreats to a far-away villa to recover from the heartbreak and humiliation of discovering his live-in girlfriend has been sleeping with his brother behind his back, his awkward bumbling with his shy Portuguese housekeeper is adorably believable. What is not believable however, is the fact that after spending a mere few weeks with said housekeeper, Jamie returns to London to learn Portuguese and then catches a red eye flight to her village on Christmas Eve to propose. Revenge sex with the hot maid or even an attempt a long-distance relationship I could get on board with, but proposing marriage to a woman when they barely speak the same language? That’s just a divorce waiting to happen and as patently ridiculous as the idea that that homely British sandwich salesman would be able to pull off a foursome with Shannon Elizabeth, Elisha Cuthbert and Denise Richards. Even women from Milwaukee aren’t that desperate.



#7 “Julian Mercer” (Keanu Reeves) Something’s Gotta Give

Okay, so I know “cougars” have been like the hot thing the past few years, but there is a difference between the April-August nuptials Ashton Kutcher and Demi Moore and the May-December relationship between Dr. Julian and famed playwright Erica Barry that goes down in this movie. Don’t get me wrong, Diane Keaton looks amazing and she should get an award for avoiding the frightening plastic surgery pitfalls that some her much younger celebrity sisters have fallen prey to. I’m just saying, anyone old enough to be an age-appropriate match for Jack Nicholson is probably just a bit too past her prime to be schtuping Keanu Reeves. As much as I’d like to applaud the character for flipping the Hef/Baby Bunny paradigm on its outdated noggin, I just can’t buy it. No way would a hot young doctor like Julian be hot for Grandma. Maybe if he had an Oedipus complex the size of Erica’s big ass Hamptons house, but that does not appear to be the case here. Plus Julian apparently forgives Erica not once, but twice for blowing him off for a crusty old senior who suffered a heart attack while attempting to have sex with her half his age daughter. Yes, we can handle the truth, but this movie is not telling it.



#6 “Graham” (Jude Law) The Holiday

Let me begin by admitting that I absolutely detest Jude Law and firmly believe that the movie Alfie was secretly a bio pic about his tumultuous relationship with Sienna Miller. The point? Any character that makes Jude Law even remotely likeable has got fairy dust sprinkled all over him. Graham is not only a successful editor, loving brother, and devoted father, but somehow manages to be completely sweet and sentimental without coming of like a total pussy, which is quite a feat for a man who tears up more frequently than a pre-menopausal woman with a raging case of PMS. I’ve dated a few cries in my time, and never was it even one-sixteenth as adorable as Grahams’s weepy goodness. Particularly when said crying was done over a brown bag wrapped bottle of Mad Dog 20/20. The moral of the story? No man who is not getting regular estrogen injections in preparation for a sex change operation would shed a fraction of the tears that Graham lets flow. And if a man in real life did cry that much it would never, never, ever be hot, sexy, cute or acceptable. Kudos to Jude, but stop spreading the lies!



#5 “Matt Sullivan” (Josh Hartnett) 40 Days and 40 Nights

This character is every ex-girlfriend’s fantasy come to life. Bitch or nice girl, when a guy breaks-up with us (or vice-versa) we all secretly hope he spends the rest of his days moping, crying and pining over us. Even if he doesn’t initially miss us, we hold out hope that when he gets the slutting it up out of his system and tries to settle down with a real girl, he’ll realize, Joanie Mitchell-style, that “you don’t know what you got till it’s gone”. But by the time he has this revelation, it will be too late and we will laugh over his desperate voicemails with our hot new investment-banker boyfriends. Muhahahahaha! Matt Sullivan delivers all this and more. He is completely smitten with his girlfriend and when she inexplicably dumps him, he can’t even bring himself to delete the 8,000 pictures and videos he keeps of her on his computer. He is basically a girl, in a cute boy’s body. Also, he somehow manages to give Shannon Sossamon an orgasm using only his breath and a flower petal. If that’s not a prime example of pure Hollywood fiction, I don’t know what is.



#4 “Andrew Hennings” (Patrick Dempsey) Sweet Home Alabama

Despite the fact that he plays a politician, Patrick Dempsey is at his “McDreamy” best in this movie. Andrew does throw one semi-justified temper tantrum upon learning that Reese Witherspoon’s character, Melanie, has been lying to him about her true identity (and the fact that she is still legally hitched to her hot but redneck first husband). However, he takes her literally leaving him AT the altar with one-eyed, one-horned, flying purple people-eater level grace and aplomb and even lets Mel punch his mother in the face (it’s richly deserved, but still). In other words, yeah, right. The man also proposes by going to Tiffany’s after-hours and telling his fiancée to “pick one”. “Prince Charming” has officially been replaced. No need to dream about a tights-wearing equestrian when Andrew Hennings is on the loose.



#3 “Ben Wrightman” (Jimmy Fallon) Fever Pitch

Red Sox obsession notwithstanding, Ben Wrightman is pretty much the perfect man. From holding back Lindsay (Drew Barrymore)’s hair while she vomits from food poisoning on their first date, to describing her little quirks as “so cute they make me want to kill myself”, to showing up at Lindsay’s door with a Red Sox onesie for a “player to be named later” post-breakup, Ben is the stuff of which relationship dreams are made. Ben does exhibit a few moments of asshatness, but more than makes up for it by going into a coma of depression when Lindsay breaks up with him and for his willingness to make the ultimate sacrifice and sell his Red Sox season tickets (worth more than $100,000) all for the love of Lindsay. Swing batta batta swooooon!





#2 “Jake Ryan” (Michael Schoeffling ) Sixteen Candles

Jake Ryan’s Tiger Beat perfection set the gold-standard of male perfection for an entire generation. He had the hot name, the sexy hair, and the fashion savvy to make 80’s prep look undeniably good. Not to mention he was a teenage boy willing to ditch his sexy, but vapid girlfriend for Molly Ringwald’s virginal Samantha Baker. Jake was so sprung on Sam he forged through her senile grandparents, an incoherent discussion with a drunk Long Duck Dong, and even let geeky sycophant Anthony Michael Hall drive his dad’s Bentley, all in order to get the girl. Did I mention he shows up at Sam’s sister’s wedding in his red Porsche to sweep her off her feet and wish her a sweet sixteenth birthday complete with cake on a glass top table when even her own family forgot? No wonder real boys stopped trying to compete in 1984. Thanks a lot, John Hughes!



#1 “Lloyd Dobler” (John Cusack) Say Anything

Take one part lovesick/heartbroken John Cusack, one part Cameron Crowe’s directorial brilliance, mix with Peter Gabriel’s “In Your Eyes”, shake well and the ultimate boyfriend myth is made. Lloyd’s unintentional cool, sweet vulnerability and underdog charm granted him instant access into the Make Believe Boyfriend Hall of Fame. Bogie’s “here’s lookin’ at you, kid” has nothing on Lloyd’s despondent “I gave her my heart and she gave me a pen”. And his boom box serenade of Diane Court is romance personified. The only thing about this movie more fictitious than the character of Lloyd Dobler was the fact that Diane(played by Ione Skye)’s response to Lloyd’s grand gesture was rolling over in bed and ignoring him, instead of running downstairs, tackling Lloyd and shagging him right there on the front lawn like any normal girl would. What’s wrong with you D. Court? Perhaps Lloyd’s aspiration to become a professional kickboxer in 1989 wasn’t exactly the most stable career path, but he was willing to give it up to go to England with Diane so she could follow her dreams. A guy confident enough with himself to be OK his girlfriend being “successful” one? Hahahahaha. Plus he gets 5,000 bonus points for being able to pull off a trench coat without looking like a flasher, a deranged psycho, or Inspector Gadget.