How George W. Bush Evolved From the Uncoolest Person on the Planet to Bona Fide Hipster Icon

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George W. Bush was once very uncool. So uncool, in fact, that in 2005, The New York Times reported that the then-president’s use of an iPod threatened Apple’s status as premier purveyor of “the electronic toys of the anti-establishment set.” The paper then asked a question: “If someone as mainstream as President Bush has caught on to something allegedly so hip, what can Apple do to keep iPod chic and cutting edge?”

Years later, toward the end of Bush’s presidency, members of the band U2 weighed whether to pose for photographs with Bush if it meant increased publicity for their charitable work in Africa. The Edge told the music magazine NME in 2009, “Hanging out with George W. Bush—which [Bono] knew was uncool, deeply unpopular in certain quarters—he knew for his own reasons that it would get results. And he was right. The amount of extra American investment in African development that occurred during that administration, compared to even the Clinton administration, was huge.”

If you are a liberal older than, say, 24—old enough to either hate Thought Catalog or not know what Thought Catalog is, is a better barometer—you know this. That George W. Bush is uncool, lame, establishment, square, and odious, etc., is a political fact as self-evident and unnecessary to argue as “Mitt Romney takes double-A batteries” or “Bill Clinton has an oiliness about him.”

But if you are younger than 24, you might not have attended anti-Bush rallies in high school and in college. You might not have pinned “SHRUB” buttons to your tote bag, and might not even remember Bush as a war-lovin’, vowel-droppin’, faux-folksy, ostentatiously religious Connecticut cowboy. This is because Bush has, quietly and wholly, ingeniously refashioned himself into an Internet-friendly, cat-loving, ironic-hat-wearing painter-cum-Instagram savant. Lately, George W. Bush is a hipster icon, and the Internet, unofficial Fourth Estate of the youth of America, is totally buying it.

Bush’s encouraging letter to student-athlete Cade Foster, the 22-year-old University of Alabama kicker who just about single-handedly (single-footedly) lost his team the 2013 Iron Bowl, is the Internet sensation of the week. How nice, Bush is, to reach out to a Troubled Youngster™! Foster’s photograph of the letter has more than 4,000 retweets; President Bush has innumerable new fans.

Though definitely aided by his love of animals, biking hobby, Internet savvy, and U-Street-friendly uniform, Bush’s transmutation from iPod-threatening lameness monster into smiling blog mascot aligns closely with his painting career. In February of this year, a hacker gained access to the e-mail account of Bush’s sister, Dorothy, and disseminated some of its content. Among the leaked documents: photographs of two of Bush’s painted self-portraits—the first America had ever seen—one set in a shower and the other in a bath tub.

Bottom left: by Stacie McChesney/NBC/NBCU Photo Bank/Getty Images; top right: by MANDEL NGAN/AFP/Getty Images; courtesy of georgewbush/instagram.

The paintings were not bad (there was an Alex Katz–influenced cleanliness and flatness to them, as we noted at the time) and the Internet took notice. “More impressive than the painting’s aesthetic quality is the soul-searching introspection evident in the scene,” *New York’*s Dan Amira wrote. “Bush, slightly hunched, is standing out of the water, staring off into the corner of the shower, as if contemplating past sins that can never be washed away, no matter how much soap you use and how hard you scrub.” What’s important here is not the generosity of the criticism but the assumption that Bush is capable of self-reflection. Bush appreciated art; an appreciation of art implies humanity, according to the enlightened classes; by the transitive property, Bush has humanity. War-mongers: they’re just like us!

Bush’s reputation as an “outsider artist” solidified with the release of each new batch of paintings. Blogs were gentle in their reviews of dozens of paintings of dogs and sunsets, and that kindness eventually and perhaps inevitably was extended to the artist himself. “15 Reasons George W. Bush Should Come Work for BuzzFeed Animals,” posted in March 2013, is the ne plus ultra of the genre. Here was the hottest new site on the Internet, run by a Brooklyn-based Yale graduate and a Huffington Post co-founder, facetiously offering Bush a job on the basis of his “[enjoying] cats” and being “as fascinated by tiny, tiny owls as we are.”

In April, the Huffington Post echoed Buzzfeed’s Bush embrace. “George W. Bush Is Planning A New Painting Series And We Can’t Wait” was a headline on the very Web site that once argued, back in 2007, “Knowledge has been [President Bush’s] enemy ever since his skull failed to completely fuse, leaving him with a spongy head and a brain that’s susceptible to bruising.” And this, also in 2007: “The fact that he speaks his fantasies and believes all of them is what makes him so dangerous. He is clearly insane and that's something few wish to face, because insanity is harder to deal with than the worst kind of prevarication. Liars get exposed, madmen get re-elected.”

And artists are forgiven. In the rich American tradition of wife-stabber Norman Mailer, unrepentant anti-Semite T. S. Eliot, full-blown racist Jack London, and Nazi sympathizer (and Jewish lesbian!) Gertrude Stein, bad reputations are mitigated by good (or, in the instance of Bush, surprisingly not-terrible) art.

In Bush’s case, this transformation has been all the easier because the arbiters of Internet cool were tween in 2007 and are far more likely to have read a Buzzfeed listicle about Bush’s dog paintings than they are to have read, say, the John Yoo torture memos. But even those old enough to remember hating Bush are wise enough to recognize that they are no longer the deciders (as it were) of what’s hip. Whereas U2 once worried about Bush getting his uncool all over their cache, Bono smiled as he posed with the ex-president at Nelson Mandela’s memorial service two days ago.

It’s a selfie at a funeral. And what could be more self-consciously of-the-moment?