Sylvester Stallone, Oscar and Stop! Or My Mom Will Shoot
Stallone and Schwarzenegger spent much of the 1980s battling for box office dominance, so when Stallone’s star started to falter around the turn of the decade (thanks to the under-performing Over the Top, Rambo III, Lock Up, and Rocky V), it probably made sense to take a page from Arnie, who’d had back-to-back comedy hits with Twins and Kindergarten Cop. And he was smart enough to get John Landis to direct the screwball-style mobster comedy Oscar, which actually isn’t that bad a movie — it’s fast and fun and reasonably amusing. But audiences clearly weren’t feeling Stallone as a comedy star, and Oscar ended up topping out at $23 million, another in his string of flops. And by the time it tanked, he already had another comedy in the can: Stop! Or My Mom Will Shoot, a painfully unfunny attempt to meld Sly’s tough-guy style with the comedy stylings of Golden Girls co-star Estelle Getty. It, too, bombed, and though he had a brief comeback the following year thanks to medium hits Cliffhanger and Demolition Man, Stallone spent most of the ‘90s turning out flops. (Credit where due: when he tried playing against type again, in the 1997 indie drama CopLand, he fared far better.)
Orlando Bloom, Elizabethtown
Cameron Crowe’s 2005 romantic comedy was a notorious stumble for the usually reliable filmmaker, becoming such shorthand for ambitious failure that it actually gave birth to a series at the A.V. Club. In that piece, author Nathan Rabin coined the phrase “Manic Pixie Dream Girl” to describe the character type embodied by Kirsten Dunst, but she’s actually not the movie’s most problematic performer. That honor goes to Orlando Bloom, whose filmography to date consisted of films like Lord of the Rings movies, Pirates of the Caribbean, Troy, and Kingdom of Heaven — in other words, big pieces of period pageantry, and nothing indicating any inclination whatsoever for romantic comedy. And in every frame of Elizabethtown, Bloom confirms that lack of flair; he overacts his already-signposted emotions, generates no chemistry with Dunst (who’s trying hard enough for both of them), and generally seems entirely uncomfortable. And after Elizabethtown laid an egg, he quickly signed on for two more Pirates flicks.
Jessica Alba, An Invisible Sign
No one’s ever gone out of their way to brand Ms. Alba as a master thespian, but in the films that made her a star — Sin City, Fantastic Four, Into the Blue, Honey — she did what she did (sexy ingénue) well enough. But even a desire to stretch those atrophied acting muscles doesn’t explain the total misfire that is 2010’s barely released An Invisible Sign, in which she plays Miss Gray, an on-the-nose-monikered, mousy wallflower of a schoolteacher dressed in appropriately atypical frumpy sweaters and TV librarian bangs. The entire project is a cutesy misfire, but Alba’s casting is its biggest miscalculation; she quickly returned to Robert Rodriguez movies, bombshell roles in films like Little Fockers, and (of course) an appearance in the upcoming Entourage movie.
Julia Roberts, Mary Reilly
Like Alba, Roberts learned the hard way that there’s a fine line between showing your range and dumping all of the charisma and excitement that made you a star. After her total box office domination in the early ‘90s, Roberts hit a bit of rough patch, thanks to the, um, troubled production of I Love Trouble and the under-performing Something to Talk About. But things really hit the skids when she took on the title role in Stephen Frears’ Mary Reilly, a Gothic horror movie that told the tale of Jekyll and Hyde through the eyes of the good doctor’s housekeeper. Frears is a helluva director who had a solid Christopher Hampton script and a well-cast John Malkovich as Jekyll and Hyde, but Roberts’ work was so dreary (and her accent so comically bad) that it derailed the movie entirely.
Robert De Niro, Stardust
De Niro pulled off one of the most surprisingly successful (from a box-office perspective, at least) career change-ups of modern movie stars when he rebranded himself as a comic actor, via 1999’s Analyze This and Meet the Parents the following year. Yet he made those choices carefully — even when doing broad comedy, he was still playing the kind of tough guy (in those two cases, a Mafioso and a former CIA agent/stern father) that he’d always done so well. That wasn’t the case with Matthew Vaughn’s 2007 adaptation of Neil Gaiman’s Stardust, which tries to subvert De Niro’s persona by casting him as a tough pirate who is actually (sit down for this) a cross-dresser who hates violence. Mincing and mugging wildly, De Niro makes no commitment whatsoever to the character — we’re just supposed to laugh at the fact that it’s him, flitting around with all the depth of a late-season guest shot on Will & Grace.
Ralph Fiennes, Maid in Manhattan
From Goeth to Dolaryhyde to Voldemort, few actors do villains as well as Mr. Fiennes; from The English Patient to The Constant Gardener, he’s also one of our best intense leading men. What he’s not so skilled at, at least based on the instantly forgettable 2002 Jennifer Lopez vehicle Maid in Manhattan, is light rom-com. The material certainly didn’t do him any favors — this was yet another early-‘00s film that found J.Lo trying to make herself over into a bland Meg Ryan clone — but the trouble is, you can see that he knows he’s slumming it, and his contempt for the picture adds an odd undercurrent to the entire enterprise.
Matthew Fox, Alex Cross
When Rob Cohen’s ill-advised attempt to reignite the Cross franchise hit theaters in 2012, several critics (this one included) had a bit of trouble buying star Tyler Perry as a gun-toting action hero. But just as disastrous was the casting of nice-guy leading man Fox (late of Lost and Party of Five) as the picture’s psycho killer. To play the frequently shirtless baddie, Fox went on an intense exercise regimen and reportedly lost something like 40 pounds — which must have left him hungry, considering how much of the movie he spends chewing on the scenery. It’s the kind of performance where you want to pull the actor aside and remind him that “most acting” doesn’t equal “best acting.”
Macaulay Culkin, The Good Son
When Culkin was cast in Joseph Ruben’s 1993 thriller, the idea was to rebrand him from the cute kid from the Home Alone movies into a real actor, thanks to a wildly against-type turn as a creepy psycho kid. But the movie was a mess, Culkin’s bad-boy playacting was barely believable, and little Elijah Wood snuck in and stole the picture. It was the beginning of the end for poor little Mac; when The Pagemaster, Getting Even with Dad, and Richie Rich all bombed the following year, he disappeared from the screen for nearly a decade.
Elizabeth Berkley, Showgirls
It’s funny to imagine now, but Showgirls was expected to be a big break for Berkley, who had spent four years playing goody-goody Jessie Spano on the dopey high school comedy Saved by the Bell. It wasn’t supposed to become one of the most notorious dogs of the ‘90s; after all, it was director Paul Verhoeven and screenwriter Joe Eszterhas following up the mega-hit Basic Instinct, and there was every reason to believe Berkley could follow in the sexpot-fame footsteps of that film’s breakout star Sharon Stone. But the hopeful actress was saddled with some of the worst dialogue and goofiest character beats this side of an Ed Wood movie; sadly, she ended up taking the brunt of the (considerable) criticism for the picture, and never quite shook off its stink — in spite of inspired turns in the likes of The First Wives Club, The Real Blonde, and Roger Dodger.
Jake Gyllenhaal, Prince of Persia: The Sands of Time
With a recent filmography that’s included Zodiac, End of Watch, Prisoners, and Nightcrawler, it’s not unreasonable to ask if there’s anything Jake Gyllenhaal can’t do. But the answer to that question came in 2010, when Gyllenhaal tried to front a video game adaptation/would-be franchise-starter. A rare flop for super-producer Jerry Bruckheimer, this mess from director Mike Newell (also well out of his depth) found the unfortunate Mr. Gyllenhaal trying — with little success — to keep his dignity intact while trudging through an increasingly silly riff on the old sword-and-sandal epics.