Gretchen Mol

Gretchen Mol
Attempts At The Big Time: Rounders” (1998), Woody Allen's “Celebrity” (1998), “Donnie Brasco" (1997), Music from Another Room” (1998)

Where Did It All Go Wrong? Here’s the thing: Gretchen Mol is an excellent character actress who has done consistent work for two decades and has really come into her own on shows like “Boardwalk Empire.” But in the late '90s, things were a bit different and not a lot of it was her fault. In 1998, in the pre-extra-super-savvy Internet days, Mol was featured on the cover of Vanity Fair fetchingly wearing a see-through slip dress and dubbed the "It Girl of the Nineties" by the magazine. The problem with this insanely premature proclamation, aside from not even having had the proper time to come true, was it was essentially based on only a handful of movies from 1997 and 1998 (basically the ones listed above)—hardly a definitive consensus what a '90s It Girl should represent. Did Mol have amazing publicists who duped Vanity Fair into thinking the moderate buzz she had was about to transform her into the next A-list ingenue? Yes, but all it really did was set up hopelessly impossible expectations for the actress (at the time, this outrageous media coup/folly was said to be the none-too-subtle bullyish work of Miramax’s Harvey Weinstein that released both “Rounders” and “Celebrity”).

Gretchen Mol Boardwalk

Making matters worse, all the aforementioned movie roles were supporting ones and when she was hoisted on the cover of Vanity Fair in ‘98 she was essentially an unknown leaving the public thinking, “Who???” and the rest of the media suppressing giggles. While Mol continued to go on doing strong character work over the years (“3:10 To Yuma,” David Wain’s “The Ten,” Neil LaBute's “The Shape of Things" and Mary Harron's "The Notorious Bettie Page" being a few examples), the perception was she was poised for greatness, “sank into obscurity” and was felled by the “Vanity Fair cover curse.” In May 2012, Mol was put on the cover of Town & Country with the title, “A star is reborn: how she broke the Hollywood curse.”

One of the elements of the Vanity Fair piece that turned out to be untrue was that Mol was discovered as the hat-check girl at Michael’s, a New York restaurant once known for its ease with which to spot celebrities. “It was the Weinsteins,” Mol said of that nonsense rumor. “[They were] in the business of making stars, with cigars hanging out of their mouths. That was the imagery. And I was a hat-check girl. First of all, who is a hat-check girl? I never checked a hat in my damn life.”

Any Thoughts? Mol felt the sting of Harvey and Vanity Fair’s big decision and watched whatever buzz she gained quickly fade. “It suddenly felt very, 'Hey, she's not all that,' ” Mol told the New York Times in 2003. ''What you find out is that just as quickly as people get behind you, they fall away. I watched as the doors went open. Then, I watched them as they closed."

Stephen Dorff

Stephen Dorff
Attempts at the Big Time: "The Power Of One" (1992) “Judgment Night” (1993), “Backbeat” (1994), “SFW” (1994)

How Did It Go Off Track? Like Skeet Ulrich and other beautiful-faced men in their 20-something prime, Stephen Dorff was on track, at one point in the mid-'90s, to be a big star. Or at least Hollywood and the media saw it that way. He had the disheveled good looks and gruff, bad-boy attitude, he smoked, drank: he was another Johnny Depp or Mickey Rourke, in the making as far as studios, magazine editors and publicists were concerned. After stints on TV including the short-lived “The Outsiders” series, 1992 saw him star in "The Power Of One" opposite Morgan Freeman at the tender age of 19, and then the following year, he scored one of the coveted leads in much-buzzed action thriller “Judgment Night.” Right around the same time as that film’s release, Dorff was cast in the video for Aerosmith’s “Cryin’” which essentially made Alicia Silverstone a star and certainly didn’t hurt him either, and reportedly he was offered the lead in TV’s “The Young Indiana Jones Chronicles”—he was on his way.

Accordingly, along came his too-cool-for-school roles, like The Beatles-centric "Backbeat" and "S.F.W.," both of which did minor business, but bolstered his up-and-coming “It-Boy” status. Soon he was living the dream: Details magazine (who actually kind of mattered at the time) called him the “best new actor of his generation” and he was hanging with R.E.M.’s Michael Stipe (they pal around with Tori Amos in a separate Details piece). Stipe even showed up the 1994 MTV Music Awards wearing a hat to promote “S.F.W.” (where he was also bumrushed by MCA).

Brake Stephen Dorff

But while Dorff’s acting chops were... fine, what seems like his undoing was the arrogance which spilled forth in interview and on set. He would dog past roles (apparently telling a reporter “Judgment Day” was so stupid he could have "phoned in the fucker"). Of actors like Sean Penn and John Malkovich he boasted, “I know if I got on the screen with them, the screen would be just blown apart.” And he relentlessly talked himself up even about roles he didn’t take/get, saying “They are talking to five young actors about playing James Dean, but I'm not chasing it because no matter how brilliant I would be, it's gonna fucking work against me."

And so the kind of fame that Dorff and Hollywood were so convinced was coming never arrived. He had some colorful moments: Mary Harron's "I Shot Andy Warhol," John Waters' "Cecil B. Demented," and "Blade," but none of these parts raised his profile significantly and it wasn’t long before he was taking parts in straight-to-DVD action movies like "Steal," "Deuces Wild" and sinking, along with Christian Slater, to topping Uwe Boll's "Alone in the Dark" in 1995.

Dorff has cleaned up in recent years, taking a small, but wise supporting role in Michael Mann’s “Public Enemies” and then making a low-key comeback vehicle of Sofia Coppola's “Somewhere.” Eran Riklis’ “Zaytoun” seemed like another step in the right direction, as was tiny indie "The Motel Life" which he was very good in, but 2011's "Carjacked" and “Rite Of Passage” demonstrate how the temptation for a paycheck gig lurks right around every corner.

Any Thoughts? Dorff isn’t exactly disagreeing with our assessment. “Yeah, I partied, and went a little crazy with the girls and had my drinking days, but I never got addicted to hard-core drugs...I think when I was younger, I was a little more self-absorbed, didn't really think of other people,” he told Vulture in 2010.

Josh Hartnett

Josh Hartnett
Attempts At The Big Time: "Pearl Harbor"(2001), "O" (2001), "Black Hawk Down" (2001),"40 Days and 40 Nights"(2002), "Hollywood Homicide"(2003), "Sin City" (2005), "The Black Dahlia" (2006) "Lucky Number Slevin"(2006) "30 Days of Night" (2007)

Where Did It All Go Wrong? Thinking about Josh Hartnett, which we do only rarely—that’s part of the problem—it’s hard to pigeonhole him into one of the other models of nearly-man: his big break, “Pearl Harbor” may have been a horrible turgid waste of an afternoon but it made money, so he’s no Taylor Kitsch. Nor has he developed a Pettyfer-like reputation for prickishness, that old story about feuding with Harrison Ford during “Hollywood Homicide” notwithstanding (and with Ford’s notoriously curmudgeonliness we’re willing to cut Hartnett some slack there). Nor are his acting chops as questionable as say Taylor Lautner’s. On occasion, Hartnett has impressed, notably in “Black Hawk Down,” “The Virgin Suicides,” intriguing if not totally successful Shakespeare riff “O” and even high-concept vampire romp “30 Days of Night.” So what went awry?

Josh Hartnett 30 Days of Night

In fact, the story now goes that Hartnett’s falling short of the A-list was as much by design as accident. In the early '00s, off the back of a host of “star of tomorrow” articles, not to mention PETA’s coveted “sexiest vegetarian of 2003” ribbon, Hartnett was offered the lead in Brett Ratner’s gestating “Superman” movie. But he turned it down, citing the ten-year commitment and his fear of being stereotyped as the reasons. Now, that movie did not come to pass, but saying no took some nerve: it’s the sort of opportunity more fame-hungry youngsters would pay PR firms just to claim they were even being considered for. And apparently he ruffled feathers, with Hartnett claiming that that decision alienated a lot of Hollywood power players, including his own agents.

Since his motives were noble, perhaps we wouldn’t deem him worthy of inclusion on this List Of Doom, if only the choices he made since then had been better. But somehow the desire to test one’s versatility as an actor seems less admirable when the results are as poor as the overplotted “Lucky Number Slevin,” the dubious “40 Days and 40 Nights” or the just bloody awful “Black Dahlia”—a film to which Hartnett was so committed to that he stayed attached to it throughout its half-decade long gestation. Even a hit like “Sin City” for his “The Faculty” director Robert Rodriguez couldn’t do much for his profile—after all, it’s little more than a cardboard role in a stacked ensemble.

More recently, Hartnett’s move indie-ward has also underwhelmed with “August,” “Stuck Between Stations” and “I Come With The Rain” ranging from just-OK to pretty bad and his upcoming Roland Joffe-directed “Singularity” plagued by production issues. In fact, the biggest blip Hartnett has made on our radar recently was as the result of a Twitter misunderstanding which had him temporarily, falsely rumored to be circling a new take on “Daredevil.” However the speed with which that took off indicates there is some latent awareness of the guy, so maybe a renaissance is not out of the question, and having recently been cast opposite Eva Green in the Sam Mendes-produced Showtime series "Penny Dreadful," suggests it could happen.

Any Thoughts? "After 'Black Hawk Down' there was a real lull. Everybody was trying to put me in action movies and heroic roles and I wanted to find more complex things. They just didn't suit my taste so I thought, 'OK, I have to be brave enough to say no.' And for a while that hurt me immeasurably in the Hollywood world. A lot of people felt jilted," Hartnett said in the UK's Daily Record in 2011.

Vehicle 19

We kept the list to ten, but other actors who fit the bill that we considered include Clive Owen (somewhat in the Farrell mode, he just can't seem to break out the way Hollywood thinks he should and has probably now settled into a respectable niche just below big-stardom) and Paul Walker, who has been pushed a couple times but outside of the "Fast and Furious" franchise has never been able to overcome a certain blandness. Jason Momoa was being put forward as a new action star after his turn in "Game of Thrones," but with his stint (season 1) just a distant memory and "Conan The Barbarian" and "Bullet to the Head" both flopping hard Drogo needs to shake it up if he's not going to slide into B-movie obscurity forever. Orlando Bloom has proved time and again just too slight a presence to be able to carry a film without the support of a massive "Lord of the Rings" or 'Pirates' machine around him; Topher Grace we mentioned recently in TV Comedy Stars Whose Big Screen Careers Faltered, so enough said there; and further back in the past the likes of Chris O'Donnell and even William "Billy" Baldwin got maybe a few more do-overs than they deserved, without making any of them really stick. And yes, we're aware how many of these choices are white and male, but whether that's because we're blinkered or because Hollywood in general doesn't make as huge a push for female stars (who are unlikely to head up a summer tentpole) or stars of other ethnicities (ditto), we'll leave you to decide.

So whose relative lack of success do you find inexplicable and who do you think has about as much chance as "Fetch!" of ever happening, no matter how high on them Hollywood might be? Let us know below. - Jessica Kiang, Oliver Lyttelton, Rodrigo Perez