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Five actors who made uglier onscreen women than Adam Sandler

Five actors who made uglier onscreen women than Adam Sandler (photo)

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I don’t think Adam Sandler will take offense if I say he makes a very, very ugly woman in “Jack and Jill.” Hell, that’s one of the main jokes of the movie — it’s even the joke on the movie’s poster — Sandler doesn’t look much like a woman, but nobody in the film seems to notice (one character even finds him attractive, more on that in a moment).

Still, Sandler’s not the first dude to look like a lady for laughs, nor is he the ugliest. He’s definitely walking in the high-heeled footsteps of some fine (but not necessarily fine looking) actors. Here’s five guys whom made even gnarlier looking woman onscreen than the former Happy Gilmore.


Jack Lemmon in “Some Like It Hot” (1959)
Directed by Billy Wilder

Although Sandler’s playing a woman in “Jack and Jill” as opposed to a man crossdressing as a woman, his film definitely owes a certain debt to “Some Like It Hot,” Billy Wilder’s classic comedy about two male musicians who witness the St. Valentine’s Day Massacre and go on the run as women in an all-girl band. In particular, Al Pacino’s role as Al Pacino, eccentric actor and millionaire who falls in love with a guy-as-girl evokes definite echoes of Joe E. Brown’s Osgood Fielding III, eccentric millionaire who falls in love with a guy-as-girl, in his case Jack Lemmon. As opposed to his co-star, Tony Curtis, who was actually quite fetching in drag, Lemmon was just a mess as “Josephine.” Which, of course, made Brown and Lemmon’s scenes that much funnier.


Edward D. Wood Jr. in “Glen or Glenda” (1953)
Directed by Edward D. Wood Jr.

In contrast, Ed Wood’s drag scenes in “Glen or Glenda” weren’t intended as comedy. Wood enjoyed dressing in women’s clothing in his private life and he made “Glen or Glenda” as a sincere if strange defense of transvestitism. The scenes illustrating Glen’s inner turmoil play out with all sorts of deranged, hallucinogenic imagery. They’ve also got Bela Lugosi screaming “Pull the string!” for no reason whatsoever. The finale, seen below, culminates in a genuinely poignant moment, when Glen’s girlfriend learns the truth and offers him the sweater off her back. It’s kind of a beautiful scene, though it doesn’t make the sight of Wood in angora any prettier.


Robert Downey Jr. in “Sherlock Holmes: A Game of Shadows” (2011)
Directed by Guy Ritchie

It takes real skill — or questionable looks — to qualify for this list on the basis of a trailer alone. But take a look at said trailer, embedded below, and just try to disagree with me that Robert Downey Jr. makes one homely lady. Presumably he just puts on this “disguise” for the one sequence during this upcoming sequel to 2009’s “Sherlock Holmes.” The sequence looks spectacular. The disguise, not so much.


Harland Williams in “Sorority Boys” (2002)
Directed by Wallace Wolodarsky

Frat boys Dave (Barry Watson), Adam (Michael Rosenbaum), and Doofer (Harland Williams) get kicked out of their frat and lose all their money, then decide to pledge a sorority where rent is free. “We don’t have to be babes, just believable!” says Dave, a.k.a. Daisy as they discuss the plan. On what planet is Williams’ “Roberta” believable? Maybe I need to get new glasses. Or get rid of my glasses altogether. The fact that Williams was 40 and playing a college student might have been part of the problem.


Arnold Schwarzenegger in “Junior” (1994)
Directed by Ivan Reitman

They say a picture is worth a thousand words. Is it also worth a thousand screams of terror? You tell me. Yikes.


What actor made the ugliest onscreen woman? Give us your pick in the comments below or on Facebook and Twitter.

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Final Countdown

The Best Of The Last

Portlandia Goes Out With A Bang

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The end is near. In mere days Portlandia wraps up its final season, and oh what a season it’s been. Lucky for you, you can watch the entire season right now right here and on the IFC app, including this free episode courtesy of Subaru.

But now, let’s take a moment to look back at some of the new classics Fred and Carrie have so thoughtfully bestowed upon us. (We’ll be looking back through tear-blurred eyes, but you do you.)

Couples Dinner

It’s not that being single sucks, it’s that you suck if you’re single.

Cancel it!

A sketch for anyone who has cancelled more appointments than they’ve kept. Which is everyone.

Forgotten America

This one’s a “Serial” killer…everything both right and wrong about true crime podcasts.

Wedding Planners

The only bad wedding is a boring wedding.

Disaster Hut

It’s only the end of the world if your doomsday kit doesn’t include rosé.

Catch up on Portlandia’s final episodes on demand and at IFC.com

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Rev Up

Your Portlandia Personality Test

The New Portlandia Webseries Is Going Your Way

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Carrie and Fred understand that although we have so much in common, we’re each so beautifully unique and different. To help us navigate those differences, Portlandia has found an easy and honest way to embrace our special selves in the form of a progressive new traffic system: a specific lane for every kind of driver. It’s all in honor of the show’s 8th and final season, and it’s all presented by Subaru.

Ready to find out who you really are? Match your personality to a lane and hop on the expressway to self-understanding.

Lane 10: Trucks Piled With Junk

Your junk is falling out of your trunk. Shake a tail light, people — this lane is for you.

Lane 33: Twins

You’re like a Gemini, but waaaay more pedestrian. Maybe you and a friend just wear the same outfits a lot. Who cares, it’s just twinning enough to make you feel special.

Lane 27: Broken Windows

Bad luck follows you around and everyone knows it. Your proverbial seat is always damp from proverbial rain. Is this the universe telling you to swallow your pride? Yes.

Lane 69: Filthy Cars

You’re all about convenience. Getting your car washed while you drive is a no-brainer.

Lane 43: Newly Divorced Singles

It’s been a while since you’ve driven alone, and you don’t know the rules of the road anymore. What’s too fast? What’s too slow? Are you sending the right signals? Don’t worry, the breakdown lane is nearby if you need it.

Still can’t find a lane to match your personality? Check out all the videos here. And see the final season of Portlandia this spring on IFC.

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Give Back

Last-Minute Holiday Gift Guide

Hits from the '80s are on repeat all Christmas Eve and Day on IFC.

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GIFs via Giphy, Photos via The Everett Collection

It’s the final countdown to Christmas and thanks to IFC’s movie marathon all Christmas Eve and Christmas Day, you can revel in classic ’80s films AND find inspiration for your last-minute gifts. Here are our recommendations, if you need a head start:

Musical Instrument

Great analog entertainment substitute when you refuse to give your kid the Nintendo Switch they’ve been drooling over.

Breakfast In Bed

Any significant other or child would appreciate these Uncle Buck-approved flapjacks. Just make sure you’re not stuck on clean up duty.

Cocktail Supplies

You’ll need them to get through the holidays.

Dance Lessons

So you can learn to shake-shake-shake (unless you know ghosts willing to lend a hand).

Comfy Clothes

With all the holiday meals, there may be some…embigenning.



Get even more great inspiration all Christmas Eve and Day on IFC, and remember…