This Sunday, in a special hourlong episode of Vice’s HBO show, Barack Obama speaks with inmates at a jail in Oklahoma during a roundtable interview hosted by Vice’s CEO Shane Smith. It is both the first time that a sitting president has visited a federal prison, and the first time that a sitting president has visited a federal prison accompanied by a man who boasted of fucking cougars, synchronized masturbation sessions with co-workers, and participated in sword-crossing threesomes.

The VICE Guide to Sex and Drugs and Rock and Roll, first released in the United States in 2003, is “a compilation of the best articles Vice Magazine published between October of 1994 and May of 2003.” It features life directives such as “The VICE Guide to Eating Pussy” and “The VICE Guide to Drugs,” confessionals in that now patented headline parlance like “A Guy Who Was on Acid For a Whole Year” and “My Mom Shot Me,” plus provocations like “Was Jesus a Fag?” and “Hey Nigger!”

But before all that is a section titled “VICE—The Whole Story.” Here, we get the tale of Vice’s genesis via conversations between Smith and his co-founders Suroosh Alvi and Gavin McInnes (since excommunicated). In honor of this weekend’s historic interview, we’ve pulled out a few stories that illustrate just how far Shane Smith has traveled from synchronized pre-work masturbation sessions during Vice’s early days to now.

For instance, Smith now runs a billion dollar company in cahoots with Rupert Murdoch that happily aligns itself with some of the biggest brands in the world. But the beginnings of Vice’s ascent up the world of publishing involved less brand synergy and more dicks and drugs.

In this passage, Smith talks about landing the company’s “first major ad” from a “big beer company” by screwing a “cougar” executive. McInnes follows that up by explaining how the three fucked Vice up the ladder, even if it meant getting in bed with “old, balding dogs with horrible tits.”

Of course, the sex wasn’t only contained to those who could make Vice rich. The founders of the company would gladly fuck their subjects, too, such as the magazine’s “girl[s] of the month.” One of those women was Amma, described by McInnes as “this slut from Malta” who “Shane and I took to fucking regularly in a porn booth and at the office.”

One of those times was a threesome that ended when McInnes says he accidentally shoved his dick inside Smith’s condom (whether you actually believe the physics of that claim is entirely up to you):

If there was no woman present to mess around with, there were always Montreal “peep shows,” which Smith enjoyed more than any of the others.

Fast forward a decade, and Shane Smith has been handpicked to shepherd the president into a federal prison so that he can speak face-to-face with young men needlessly incarcerated in his country. One assumes Obama has never read McInnes’ “VICE Guide to Anal Sex.”

Hope springs eternal for all of the media’s weird fucked up creeps.

Contact the author at