The 2009 Sexy Ugly Awards

We’ve all seen lists of the top 100 sexiest people alive, best bums, cleavages or whatever. They’re usually filled with your usual suspects: Brangelina, Jessica Alba, Beyonce, Clooney, Matt Damon, Johnny Depp, Colin Farrell…

Ahem. Anyway, my point is that we’re all familiar with the most beautiful people in the world but what about moderately attractive people? When will they get a break?

After seeing all the hype surrounding The Road this week, I realised that Viggo Mortensen is NOT Aragorn. I know most of you already figured that out but I was comfortable with my delusion that he really was a sword swinging hero who looked damn hot covered in sweat, dirt and orc blood…

Having said that, I still would – but who else will join him on my list of Hollywood’s ugliest sexy people…

(This article is dedicated to one of my favourite indie movies, Kissing Jessica Stein, which inspired this genius way of describing someone.)


Vince Vaughn is totally the example of how funny guys get chicks. He looks like he hasn’t slept in years, he doesn’t take care of his body and he’s got a receeding hairline.

On top of that, so many of the characters that he’s played have basically had a story of ‘I’m incapable of a mature, loving relationship. Oh wait, no I’m not.’ (Thanks Family Guy)

But he’s super funny and confident which is always attractive so you can kind of understand how he managed to bag Jennifer Aniston for a while. It seemed like Vince was a confirmed bachelor until recently when he actually managed to get married.

Speaking of marriage, here’s clip from The Wedding Crashers.


She may have been having tons of sex in the city but sometimes I wondered why, cause it definitely wasn’t her looks. Charlotte is obviously the prettiest SATC girl and Samantha was the nympho so I couldn’t quite understand why Carrie was always the centre of attention.

But after extensive reviewing of the original seasons (all for research purposes, of course), SJP grew on me and I saw her inner beauty. OK she’s half and half pretty and ugly but we’ve all grown to love her over six seasons and a movie so I’ll let it slide.

And this list is not meant to be mean spirited, I think all of our winners are sexy (but sexy ugly), but I have to share with you a Youtube comment made about SJP that had me laughing. Mubble said, ‘She looks like a boiled horse.’ Excellent.

Here she is in a Matrix spoof.


Tall, muscular, can fix a car and looks good in a vest. Those are Fast and Furious star, Vin Diesel’s, good qualities. That’s what makes him sexy.

It’s his potatoe/rock shaped head and his Rocky Balboa speech patterns that earn him a place on my list. His acting skills really have very little to with our attraction to him because, quite frankly, we haven’t ever seen them.

Vin’s sex appeal lies solely in his big, broad shouldered body and you know what, I’m comfortable with that. Here’s Vin getting it on with Avatar’s brutally underused Michelle Rodriguez in The Fast and The Furious. And may I just say: one of our favourite ass grabs in a movie ever.


Even when he was young, his hairline looked old. Bruce Willis’ hair has been receeding since he was in nappies. He’s not a well cut, muscular guy and he’s isn’t what you’d call handsome nor is he that funny.

However, there is some undefinable quality that makes Bruce Willis hot as hell to some women. Maybe it’s just the sheer manliness of him; big, strong, protective and willingness to jump off of tall buildings with a hosepipe tied around his stomach.

Bruce also has a sensitive side to him that of course combined with the protectiveness just drives women wild. Plus he stays best friends with ex-wife Demi Moore as she frollicks with her boytoy. Take a look at this picture – wouldn’t you?


I thought a lot about this one and determined that yes, Kirsten Dunst is in fact, sexy ugly. The reason I toyed with including her is whether or not she’s classed as sexy.

Some might class her as just pretty or attractive but I took a bold step and now she’s sexy. Just sexy ugly.

The movies that tipped me over the edge into sexy were Crazy/Beautiful and Marie Antoinette. The thing that qualifies her for the ugly part is small, some might say insignificant but it’s her mouth. Take another glance you’ll know what I mean. I don’t mean to be rude so I’ll just say it rhymes with ‘fraggle booth’.

Anyway, let’s celebrate the sexy part by having a look at the raunchiness of the French royalty in Marie Antoinette.


Vince Vaughn and Seth Rogen have one thing in common: they both use comedy to get chicks. That must be how they do it.

Seth doesn’t exactly look like the back end of a bus but he’s not your typical leading man. Messy, curly, slightly ginger hair isn’t usually what gets the ladies going, nor is it traditionally attractive when your laugh makes you sound like you’re a Yeti.

He’s tubby (though not anymore since training for the Green Hornet movie) and he’s an avid pot smoker. Sounds like a real winner, right? And yet all of these qualities only make women love him more. Can you imagine Knocked Up being true to life with Katherine Heigl going for Seth?

It’s a paradox and I’m expecting the universe to collapse in on itself any day now. In the meantime, let’s see him get chatty with American chat show King, David Letterman.


Puerto Rican and a movie star? He must be so good looking. Well, not so much actually. Benicio Del Toro has a career as a well respected character actor, most recently seen as scruffy revolutionary/fashion icon Che Guevara.

While not being classically handsome, Benicio rocks the dark, brooding look but at the same time looks a little bit like a dog. I think it’s the exceptionally long sideburns. Which is quite befitting considering that Benicio’s next film is the much anticipated and much delayed Wolfman.

Benicio’s wild eyed performances in Sin City and Fear And Loathing In Las Vegas also give him an unpredictable, exciting quality that makes most women fall all over themselves.


Owen Wilson is almost the exact definition of sexy ugly. He’s funny, got a good body, he’s a good actor and he’s got a big ass broken nose. A perfect combination.

He put these qualities to good use as Hansel in the hilarious Ben Stiller movie, Zoolander. I also know that he’s a real sensitive soul and emotionally vulnerable as he had a little accident/suicide attempt after he broke up with serial dater, Kate Hudson. So now he’s Mr. Sensitive too.

While occasionally I’ve got some issues regarding his hair, for the most part it’s all good.


Wild eyed Elvis fanatic Nicolas Cage rounds out our list because there’s something not quite right about him.

In his 90s heyday, Cage was all set to be the next action hero and proved that he could muscle it out with the big boys in Con Air. But his sensitive, soulful eyes and his penchant for saving the day couldn’t quite cancel out the weirdness factor.

Cage is well known in Hollywood for having strange behaviour and while in Benicio Del Toro that’d be a total turn on, Cage doesn’t have a dark enough persona to pull it off. He’s just comes off awkward and potentially dangerous in a drug addled ‘I just ate my hamster!’ kind of way.

But every woman who saw City Of Angels cried like a banshee and fell in love with Nic Cage. While his movie choices are, to put it nicely, varied, he never really rings the big money bell and so is forced to act out in smaller roles. This means that his entire female audience is torn between fawning all over him and wondering why he can’t get a better part.

But just for the record, even though his character was hella crazy for the first half an hour, I would totally jump on him in Face/Off. You can next catch Cage in Kick-Ass but here he is feeling…religious.



Jeff has always had a kind of geeky chic style to him and has played a scientist so many times he was almost typecast.

Sometimes he’s sexy just like he is in Jurassic Park (but not the sequel ’cause that sucked) in a leather jacket and sunglasses. But most other times he’s just awkward and too tall to be human.

Jeff has these funny little mannerisms that he can’t seem to shake off not matter what show or movie he’s in. He’s kinda good looking and tall is usually a bonus but as a whole package there’s something that’s a little off.

Maybe it’s the Clark Kent effect with the glasses…


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