Pretty young things: how Leo, Brad, Johnny and Winona redefined the 90s A-list

Call it unbridled nostalgia, circular fashion, or millennials coming to appreciate all that came before, but the 90s are writ large on our consciousness. I can say ‘our’ here, though only just. Born in 1991, I was technically too young to fully appreciate much of it. Perhaps the most compelling case for my belonging to the 90s at all was a chaste schoolgirl crush on Leonardo DiCaprio and subsequent ownership of a VHS tape aptly entitled ‘Leo-Mania’.

But even for Gen Z teenagers who’ve never known DiCaprio as anything but a supermodel-dating prestige actor, more at home as a grizzled 19th century frontiersman than a straw-haired pretty boy, the decade’s iconography has its lures. Stills and gifs from Baz Luhrmann’s 1996 film Romeo + Juliet remain popular, and why wouldn’t they? That fish-tank meet-cute between DiCaprio and Claire Danes has become embossed on our memories. Winona Ryder’s ultra-cool femme goth vibe has never really gone out of style. The matchy-matchy blondeness of It couple Gwyneth Paltrow and Brad Pitt was short-lived but intense, and the photos of them together are periodically shared on social media with relish. So what is it about 90s stars that continues to give them such appeal? 

For one thing, the on-screen man was evolving. As the mid-90s approached, the box office popularity of previously reliable 80s macho men like Arnold Schwarzenegger was waning. In spite of huge success with Terminator 2 in 1991, by the time of Last Action Hero’s release in 1993, machismo was out of style. More traditionally action-oriented A-listers like Tom Cruise would do some soul-searching in this decade. He entered the 90s well-known for Top Gun (1986) and would continue to do what he did best in Mission: Impossible (1996), but he also experimented with his image. In Interview with the Vampire (1994), Cruise made a major departure as the vampire Lestat, wearing long hair and 19th-century dress. In 1999, we got the double-whammy of Stanley Kubrick’s Eyes Wide Shut, where Cruise is a married man grappling with sexual insecurity, and Paul Thomas Anderson’s Magnolia, where he is a comically paranoid men’s rights advocate who shouts at his followers to “Respect the cock.”

Meanwhile, a crop of younger stars and It boys would wallpaper bedrooms with their Tiger Beat photoshoots. By 1998, in the wake of Titanic’s success, ‘Leo-mania’ had taken over. He graced multiple magazine covers from Seventeen to Rolling Stone, and his status as a teen pin-up was treated with a seriousness that Hollywood only affords its box office darlings. There had always been pretty-faced boys and teenybopper idols, but this felt like something fresh: could these heartthrobs have artistic integrity, too?

In 1995, during that pre-Jack Dawson period, baby Leo played symbolist poet Arthur Rimbaud (Total Eclipse) and a troubled junkie youth (The Basketball Diaries). With Sundance and Miramax providing fresh opportunities for independent directors and alternative perspectives, American moviemaking was letting its teen idols’ work be taken seriously. The likes of Brad, Leo and Johnny seemed to look good shirtless and have critical credibility.

The introspective male was not only attractive but seemed to be an identity taken on in earnest by the culture of the decade. In literature, David Foster Wallace dispatched gender stereotypes with unparalleled insight; in music, Kurt Cobain fought back against stupidity and sexism in rock. The cross-pollination of fashion and music into mainstream cinema – while clearly not novel – began to create a zeitgeist around certain stars. There was a vogue for snake-hipped, effete boys with cheekbones, à la River Phoenix and Johnny Depp. Even more so for luminous, ultra-thin white girls (they were almost without fail white) like Gwyneth Paltrow and Winona Ryder. Post-Nirvana and Riot Grrrl, films like Empire Records (1995) and Reality Bites (1994) tapped into a misanthropic alternative energy that celebrated outsiders and slackers. 

The male stars of these films were the fashionably disaffected likes of Ethan Hawke, a too-cool-for-you type who made his name in Richard Linklater’s sensitive Before trilogy. But Hawke shared something with his fellow heartthrobs River Phoenix, Johnny Depp and Brad Pitt: these delicate-boned men could all pass for boy-poets, or skinny rock stars. In 1998, Republican senator John McCain spoke unkindly about DiCaprio in an interview, referencing his daughter’s love for him and accidentally summarising the changing landscape of how men were perceived: “Like every other 13-year-old in America, she’s in love with Leonardo DiCaprio, who I think is an androgynous wimp.” 

Of their roles in the 90s, most of these heartthrobs played types that would feed into the, well, ‘androgynous wimp’ category: Depp as a romantic drifter in Jim Jarmusch’s monochrome western Dead Man (1995), Pitt as the thoughtful Louis in the clearly homoerotic Interview with the Vampire, and River Pheonix alongside Keanu Reeves in Gus Van Sant’s inventive My Own Private Idaho (1991), a thoroughly adult examination of the lives of a pair of street hustlers and transients. 

It’s fascinating to consider Brad, Leo and Johnny’s evolution into A-listers and power players as they grew older. Unlike most actresses in Hollywood, their ageing has made them no less desirable to legions of fans. On screen, the sensitive personas and independent spirit of these male stars didn’t always last. Johnny Depp, drowning in money from his many dull franchise projects, has not made an interesting – let alone independent – film in over a decade. In 2016, Depp was accused by ex-wife Amber Heard of domestic violence and abuse. The idealised rebel troubadour of decades previous was long gone, and with the actor now legally contesting the allegations, it makes for an ugly reality. 

But it’s DiCaprio who proves to be the most striking example of an evolving screen image. Post-Titanic, he has gone from one box office triumph to the next, with few exceptions. He’s worked almost entirely with beloved (male) filmmakers. Spielberg and Scorsese both used his boyish charm to great benefit in Catch Me if You Can (2002) and The Aviator (2004) respectively. But these days he’s a leading man whose roles have aged with him, not simply in years but to match his weathered, party-boy countenance. Fathoming the sweet-faced boy in Romeo + Juliet as the smug, chauvinistic man in The Wolf of Wall Street (2013) might require some mental gymnastics, but it’s helped along by DiCaprio’s rep in real life. For a time, he led a crew of Hollywood womanisers that charmingly referred to themselves as the ‘Pussy Posse’. 

This misbehaviour – and the way it’s been laughed off – stands in stark contrast to so many of Leo and company’s female co-stars. It almost doesn’t bear repeating, but double standards were rife. Several of the It girls of the time seem to have had fallow periods in their careers in a way the boys simply did not. Winona Ryder, after being disproportionately humiliated for a shoplifting incident in 2001, became persona non grata for a while and took a break from acting. She would return, and, thanks to Netflix’s Stranger Things, make a strong impression on another generation of viewers. Claire Danes, DiCaprio’s winsome co-star in Romeo + Juliet, worked consistently but failed to find a leading role comparable to what had come before. In a triumph of a career resurgence, her starring role as a CIA agent in Showtime’s Homeland has been lauded across the board. After reaching mega-stardom aged only 19 in Clueless, Alicia Silverstone was publicly ridiculed for her weight and became a regular target for the press. One reporter cruelly wrote of her weight gain that she looked “more Babe than babe”. It wasn’t long before she chose to move to the stage and out of the limelight. Even Gwyneth Paltrow struggled to find much success between 2000 and 2008 – until she joined the cast of Iron Man and became part of the unsinkable MCU. 

What’s evident in hindsight is that the appearance of change is rarely change itself. Nineties cinema’s propensity for brooding, self-critical manhood was nowhere near enough to encourage meaningful change for women in the film industry. Nor was it a catalyst for men to truly reckon with the misogyny they perpetrated. The gender pay gap would remain, the media would continue to relentlessly ogle and condescend to young female stars, and, most glaringly of all, the star-making and -breaking machine of Miramax – helmed by the serially accused Harvey Weinstein – would continue to exploit and discard talented young women at will. 

It’s interesting to note that several of the women who’ve spoken out about Weinstein were very close to the male stars I’ve mentioned. Brad Pitt’s ex-girlfriend, Gwyneth Paltrow, along with his former wife, Angelina Jolie, were allegedly subject to harassment, abuse and threats from Weinstein in a way that most famous men could scarcely imagine. Pitt allegedly confronted the mogul about it. Ethan Hawke’s ex-wife, Uma Thurman, has also spoken about “wriggling away” from Weinstein’s grasp. It may not be a reflection on these actors, but it is a reflection of what was a jagged divide between an It boy and an It girl in 90s Hollywood. I might optimistically point out that many actresses survived and even thrived in the Weinstein era and beyond with their careers intact. But so many others can never be accounted for, were never afforded the chances their male counterparts received, and were abused, pigeonholed, or harangued by a sexist media. Whether they were victimised like Annabella Sciorra or, like Juliette Lewis, seemed to fall off the radar, our cultural landscape became weaker without them. 

Surveying all of this, I can’t help but think of the upcoming release of Once Upon a Time in… Hollywood, Quentin Tarantino’s new film starring Pitt and DiCaprio. It’s a 90s dream-team, of sorts, putting the two together on screen for the first time, and in front of the lens of that decade’s breakout American film director. In spite of everything, it seems that those 90s boys are doing just fine. 

The season Nineties: Young Cinema Rebels ran at BFI Southbank from July-August 2019.