By Jake Flanagin
Heartburn!  Weirdly lovable, even in 2013.

Heartburn! Weirdly lovable, even in 2013.

Some say Gatsby is cursed. No one has been able to produce a crowd-and-critic-pleasing version since Herbert Brenon’s 1926 adaptation. This doesn’t bode well for Baz Lurhmann’s Jay-Z-scored, 3D art deco orgy, set for release this May. Judging by the trailer, Luhrmann’s film is phenomenally cast and visually stunning, but is that enough to break the curse? If Robert Redford couldn’t do it, who’s to say DiCaprio can?

To set your expectations nice and low — and to psyche you up for the Oscars this Sunday, which will feature such book-based hits as Life of Pi, Silver Linings Playbook, Anna Karenina, Les Misérables, and Lincoln — here are 10 botched literary adaptations nearly saved by shrewd casting decisions.

Meryl Streep in Heartburn (1986)

“It’s horrible to have a flop,” Nora Ephron wrote in her 2011 essay collection, I Remember Nothing. “It’s painful and mortifying. It’s lonely and sad.” My fellow Ephronophiles know exactly what she’s referring to: her 1983 semi-autobiographical divorce comedy, Heartburn. The reviews were mostly negative and ticket sales negligible, but Meryl Streep’s portrayal of the frank and endearingly anxious Rachel Samstat picked Heartburn up off the floor, dusted it off, and quietly placed it alongside other underappreciated cult favorites. Now, whenever I reread my Pepto-Bismol-colored copy of the original novel, it is Streep, not Ephron, I imagine smashing a key lime pie in her philandering husband’s face.

Martin Freeman in The Hobbit: An Unexpected Journey (2012)
Peter Jackson’s return to Middle-earth was the bitterest of let-downs. The 169-minute film, part one of the Hobbit trilogy, attempts to copy the epicness of The Lord of the Rings, but it comes off like a promo reel for a Middle-earth-themed ride at Universal Studios. But Martin Freeman shines as the bumbling, Colin Firth-esque young Bilbo Baggins: self-deprecating in that quintessentially Anglo manner with which Tolkien imbued these furry-footed little heroes. His performance is an energizing departure from the film’s exhausting, start-and-stop action sequences — and may be the only reason I choose to sit through parts two and three.

Helena Bonham Carter in Alice in Wonderland (2010)
A technicolor fever dream. Such is Tim Burton’s prevailing sensibility, but his take on Lewis Carroll's masterpiece is lurid overkill. Still, in Burton’s most ridiculous production choice lies the film’s sole redemption: Helena Bonham Carter as the bobble-headed Red Queen. A deranged Elizabethan Powerpuff Girl, she serves as a much-needed counterweight to Anne Hathaway’s saccharine White Queen.

Bette Midler in The First Wives Club (1996)
Predictably, most of the negative reviews for Hugh Wilson’s The First Wives Club came from male critics. Divorce-revenge comedies do appeal to a very niche demographic, but my chief issue with this adaptation of Olivia Goldsmith’s 1992 novel lies in its flagrant miscasting of Diane Keaton. Keaton, who flounders as the mewling Annie Paradis: a character woefully undeserving of her talents. But Bette Midler keeps The First Wives Club afloat with her portrayal of the buxom and brazen Brenda Cushman. The bullheaded ex-wife of an electronics superstore magnate, she's never short of a sharp retort or unsubtle Mafioso threat, proving that it sometimes pays to typecast.

Nicole Kidman in The Golden Compass (2007)
Chris Weitz’s 2007 fantasy adventure, based on the first novel in Philip Pullman’s His Dark Materials trilogy, was a shameless attempt at replicating the franchise buzz behind Harry Potter, The Lord of the Rings, and the like. The result was a warmed-over screen adaptation that aimed to please both young and adult audiences, while alienating both. But Nicole Kidman’s portrayal of the courtly Marisa Coulter makes for a truly intriguing villainess — something like a treacherous alternate-reality Bond girl. 

Andy Serkis in Inkheart (2008)
I honestly couldn’t tell you who fumbled the project, based Cornelia Funke’s bestselling children’s fantasy, the hardest: Brendan Fraser or Warner Bros. The only compensating decision made by director Iain Softley was to cast British stalwarts Jim Broadbent, Helen Mirren, and Paul Bettany, who can really do no wrong. But it’s Andy Serkis, the voice and flailing limbs behind Gollum, who both terrifies and fascinates as Capricorn. I don’t know why, but bald-headed roles seem to be his forte.

Hallie Kate Eisenberg in Bicentennial Man (1999)

You know you’ve got a flop when the resident scene-stealer is a seven year-old in a supporting role. Hallie Kate Eisenberg — yes, the little girl who belted out Aretha in those late-90s Pepsi ads — manages to sidestep all the forced sentimentalism of this Chris Columbus adaptation of Isaac Asimov and Robert Silverberg's novel, The Positronic Man. As “Little Miss,” Eisenberg is adorably earnest, outshining Sam Neill, Oliver Platt, and even a post-Doubtfire Robin Williams. Some might say the saddest part of Bicentennial Man comes at the end; I say it comes when Little Miss grows up, and Eisenberg is replaced with the emotionally leaden Embeth Davidtz.

Annette Bening in Running With Scissors (2003)

Expectations were high for this big screen depiction of Augusten Burroughs’ bestselling memoir. Those expectations were not met. The Orlando Sentinel called it “Igby Goes Down without the laughs,” while the Philadelphia Inquirer described the book as "deadpan" and the movie as “more or less dead.” All in all, there’s not much to be said for this fumbled dramedy — save for the erratic and unbalanced Deirdre Burroughs, played by Annette Bening. Bening plays Burroughs’ negligent, fame-obsessed mother with such alarming authenticity that we have to wonder if there’s not a little nugget of sociopathy hidden behind those baby blues.

Melanie Griffith in The Bonfire of the Vanities (1990)

Brian DePalma’s reworking of Tom Wolfe’s infamous satire takes first prize as the single-most upsetting literary adaptation ever made. Variety called it a “$45 million-plus dud.” The only halfway redeeming aspect is Melanie Griffith’s hypersaturated performance as seductress Maria Ruskin — a part so sickly sweet and over-the-top David Lynch could have written it. 

Sam Waterston in The Great Gatsby (1974)

Finally, we come to the Everest of adaptations. Some would say no one but Herbert Brenon could pull it off. Roger Ebert described Jack Clayton’s 1974 take as as “faithful to the novel with a vengeance — to what happens in the novel, that is, not to the mood, feel, and spirit of it.” While Robert Redford’s Jay Gatsby is accordingly all shimmer and no shine, Sam Waterson plays Nick Carraway with the honest affability and wide-eyed guilelessness essential to Fitzgerald’s smartly crafted narrator — no doubt informing later good-guy roles like Law & Order’s Jack McCoy and The Newsroom’s perpetually bowtied Charlie Skinner. Tobey Maguire has some big (wingtip) shoes to fill.