Look. Only Pitt and Rahm are photographs. Obama — like Uncle Sam — is done with artwork. Pretty bad artwork. It looks like a bad drawing, and I'm guessing it was done by computer-processing of a photo. It's funny the way the photographiness of a photo shows through when a drawing is made. Something more timeless and grand is found when the artist draws from life. Of course, there's the usual risk that it won't look like the person. But that's why you need a good artist. Or stick with a regular photo-photo.
Unless you're looking for an odd effect. Perhaps Drudge is trying to say that Obama is drained of life. It might have something to do with the big drained-of-color idea, which does unify the 4 images. There's another processed photo further down on the page: Hugo Chavez. His image has been subjected to posterization — where all shades of gray have been eliminated.
Ah! I said it: shades of grey. Is Drudge hinting that these men have some kind of Christian Grey sadistic power over us? Speaking of photoprocessing, there was this article in the Daily Mail yesterday, imagining Christian Grey as a composite — depicted in shades of gray — of various famous guys, including Brad Pitt (but not Rahm, Uncle Sam, Obama, and Chavez).
Also on the Drudge page, in column 1, under Brad Pitt, is Vladimir Putin. Putin and Pitt are both wearing sunglasses. The Pitt image pushes "Brad Pitt's mom in fear after slamming Obama..." and the Putin image goes to "West is on decline." Chavez is positioned under Uncle Sam, and both of those images include hands — Sam pointing at us (over a warning about taxes and Obama) and Chavez with his hand to his forehead in the position Drudge showed Obama 3 days ago. Obama had his hand like that along with the headline "Barack and Bones: I've Been Eating," and today's Chavez image goes along with an assertion that Chavez is "totally free" of cancer (a likely lie).
The main story, about Rahm ("the Godfather") is about the murder rate spiking in Chicago. Rahm's picture is centered over Uncle Sam and Hugo Chavez, and Rahm's hand is holding his chin in a manner that implies thinking and judgment especially given the intensity of his eyes, looking off to his right. Uncle Sam's eyes are also intense, staring right at us in that accusatory way. As noted above, Pitt and Putin have their eyes covered with sunglasses — shades (Shades of Grey?!). So what might we say about Obama's eyes? I'd say they look up slightly, conveying vague confusion or dreaminess.
Obama tops the third column, which has no other faces, but 2 other images: of solar flares ("getting stronger") and of NYC ("Bloomberg asks developers to test tiny apartments..."). The Obama image has "$0$" under it, which links to a story about how Romney raised much more money than Obama in June ($106 million, compared to $71 million).
What does it all mean? The easy explanation is that black-and-white imposes unity over the diverse images, and the similarities and differences are mostly by chance, aided by a bit of conscious design (putting the sunglasses pictures in one column and the hands pictures in another). Black-and-white was a big move by Drudge, but it too is likely meaningless. Just another way to get attention. Maybe he thought going black-and-white with the Rahm picture made him look more like a gangster (even though the "Godfather" movies are in color), and that led to the idea of making the whole page black-and-white, just to get the webfolk thinking, making stuff up.
But the only interesting lead I thought of is "50 Shades of Grey." Maybe Drudge is trying to say that government and crime are whipping us into submission. Government and crime... and solar flares. Wear sunglasses!