Playing the Hollywood Historian...
After the massive success of their first "Hollywood Issue" and its lingerie'd ladies (see: episode 1), Vanity Fair followed up with "Boy's Town" in 1996 which got a teensy bit of crap for its contextual sexism: women as sex objects the first year; men following fully clothed the next.
This double standard has been going on for as long as Hollywood has been a concept. I used to think that even if they had wanted to they could never have convinced the semi-established male stars to undress for the cover . It would have been deemed as too feminizing or, well, gay. But lately... now that most actors, and numerous civilians too, are carefully sculpting porn star bodies for themselves; with exhibitionism still growing and private boundaries still shrinking, I'm not so sure that it couldn't happen if Vanity Fair were a little edgier. (They're not. More on that when we get to 2006.)
But anyway, the boys...
Vanity Fair changed their tune here to some degree. All of the women in the previous cover were already established as actors/celebrities (most hadn't peaked) --Annie Leibovitz was photographing a mix of established and barely knowns this, the following year.
Tim Roth nearing 35 was a totally understandable choice for the cover. Everyone connected to Quentin Tarantino and Pulp Fiction (1994) was still hot and Roth followed up his indelible opening sequence success as Fiction's "Pumpkin" with an Oscar nod for his scene-stealing villain in Rob Roy (1995). It was rather strange, given that he's still a respected actor, that his stardom peaked just as it began but good news: a movie comeback may be just around the corner. He's in Francis Coppola's Youth Without Youth (about to open) and he has five films lined up for the next couple of years including a fourth collaboration with Tarantino. If those movies all happen, that's a lotta Roth. Or at least a lot more Roth than we've grown accustomed to.
Leonardo DiCaprio, a veritable spring chicken at 21 years of age, was already skyrocketing. Hollywood's elvish boy wonder --just a slip of a thing at the time, the beefiness was well in the future --had an Oscar nomination for What's Eating Gilbert Grape (1993) behind him, already had major Hollywood supporters (Sharon Stone, an early adopter) and had held his own onscreen with Stone, Russell Crowe and famously with Robert DeNiro in This Boy's Life (also 1993). The year before this cover arrived he cemented his "one to watch" status with the triple play of The Basketball Diaries, Total Eclipse and The Quick and the Dead. Baz Luhrman's Romeo + Juliet was next and would be his first hit.
...and then he got on some rickety boat with Kate Winslet.
Matthew McConaughey at 26 had been anointed "the next big thing" on the strength of his casting as the lead in A Time To Kill. But when this cover arrived he was still only a hot property in theory. He had had small roles in Dazed and Confused (1993) and Boys on the Side (1995) among others. Luckily for McConaughey A Time to Kill turned into a hit but Vanity Fair, just to help that along, gave him another cover before the public cared. They'd later pull a similar trick with Gretchen Mol prompting media watchers like moi to wonder if they owned stake in particular careers. The rest is mainstream "sexiest man alive" mall culture history.
Benicio Del Toro is the only coverboy here to win an Oscar (Traffic, 2000). It's hard to believe this weathered terrific actor was ever 29 but he was. Before this cover was shot he'd had a series of supporting roles and was fresh off the surprise success The Usual Suspects (1995). He's had a steady career ever since --never a huge star but never unemployed-- and most recently played lead in the grief drama Things We Lost in the Fire with Halle Berry. Only 12 people saw it but that doesn't change the fact that he was incredible in it.
Michael Rapaport oops -- I had to look up his name (oops) though I recognized the face. He was 26 and had just worked with Woody Allen on Mighty Aphrodite (they'd reteam again for Small Time Crooks in 2000). Lead roles didn't really materialize but he's kept busy on television as a series regular in various shows like Boston Public and The War at Home.
Stephen Dorff, in leather pants (hello 90s!) was about to turn 23. Like DiCaprio he'd been a sitcom child actor who had graduated to major film roles by the early 90s. His chief claim to fame at the time was a well received leading role in another triumph of the human spirit drama from Rocky director John Avildsen called The Power of One (1992). Afterwards he was part of the Beatles drama Backbeat (1994) and he probably wore these same leather pants in the indie S.F.W. aka 'so f***ing what" (1994) with Reese Witherspoon. Many expected his career to keep growing and it probably should have. He was quite good as the transsexual Candy Darling in I Shot Andy Warhol (1996) and also had fun with his crazy movie-maker title character in John Waters Cecil B DeMented (2000). But the lead roles stopped. Ever since his arch villain role in Blade (1998) he's often been found menacing from the sidelines. Sometimes without his pants on. I think of his early career trajectory and I keep seeing Ben Foster showing off right now -- is the same future in store?
Jonathon Schaech, 26, was not well known. His sole minor claims to fame were three: catching Winona Ryder's eye (briefly) with his dripping muscled physique at a public pool in How to Make an American Quilt, licking cum from his hand as "Xavier Red" in Gregg Araki's Doom Generation and being cast in That Thing You Do! directed by Tom Hanks (which hadn't yet surfaced -thx for the reminder commenters) These three accomplishments are not the sort of thing that normally lands one on Vanity Fair covers but it happened anyway. What didn't happen was the big stardom though he certainly tried, keeping busy as an actor and marrying Christina Applegate (they divorced this summer). I'm absolutely convinced he was cursed by being ahead of the curve... look where a hot bod and decent acting chops will get you these days [see: Chris Evans' career]
David Arquette. The youngest member of the enduring Arquette clan had had a pretty unremarkable career by this point at 24 years of age and a pretty unremarkable one afterward... a movie here, a television show there. His biggest success, the Scream franchise, was just around the corner but he's stayed very famous. I guess it helps to plague the populace with endless collect calling commercials and marry a television star at the peak of her fame. You didn't ask but Roseanna and Alexis are totally my favorite Arquettes, no contest.
Will Smith gets the same back cover placement as Angela Bassett the preceding year. You probably noticed. You might be screaming 'racism!' but this is what time travelling is about: Will Smith was not always WILL SMITH. He's been such a massive star for so long that we forget he was once just a 26 year-old television star with a rap hit "Parents Just Don't Understand" under his belt... but even then Jada Pinkett and kid were at his side (photo proof, left). That's longevity right there. The mega-billions future was not a given though he had suggested it would be with Bad Boys, his only movie hit to open before this cover. Independence Day would open in the summer of 1996 and after its $300 million gross, Will Smith was WILL SMITH.
Skeet Ulrich, would eventually come to be dubbed "the poor man's Johnny Depp" for his resemblance to 21 Jump Street era Depp. But he still wasn't famous enough to be dismissed by the comparison. He was 26 and a complete unknown. His appearance here was undoubtedly a mark of two things: the massive swinging cajones of his agent and publicists. He was being cast right and left despite having only appeared as "thug" in the first Teenage Mutant Ninja Turtles movie and a CBS telemovie. In 96 and 97, he would be featured in roles big and small in seven movies: most famously The Craft, Scream and As Good as it Gets. By 2000 he was making DVD sequels to films like Hackers. It looked like a really short career until television's Jericho rescued him from impending obscurity... for now.
median age: 26, younger by 4 years from the girls the year before, which is a little weird when you stop to think about the fact that female actors generally become famous earlier in their lives than male actors --who usually don't peak until well into their late 30s and 40s. But perhaps it's not so odd when you consider that Vanity Fair had moved from rising star women to celebrating relatively unknown men.
collective Oscar nominations before this cover: 2, the men responsible are on the actual cover
collective Oscar nominations after this cover: 5 with 1 win ( Del Toro in Traffic)
fame levels in 2007, according to famousr, from most to least: Will Smith, Leonardo DiCaprio, Matthew McConaughey, David Arquette, Benicio Del Toro, Tim Roth, Stephen Dorff, Michael Rapaport, Skeet Ulrich and Johnathon Schaech
more episodes: 1995 ,1996, 1997, 1998, 1999, 2000 and 2001