Anne Hathaway: Havoc (2005)
Oscar Nomination: Best Supporting Actress, Les Misérables
Despite her penchant for painfully awkward awards speeches and her cult of haters, Anne Hathaway is a virtual lock to win the best-supporting-actress Oscar for her poignant turn as doomed prostitute Fantine in Les Misérables. Her weepy, hyperventilating rendition of “I Dreamed a Dream” is arguably one of the finest “Oscar moments” of the year, after all. But before she dazzled in Les Miz, Hathaway starred in the so-bad-it’s-hilarious misfire Havoc. Directed by Oscar winner Barbara Kopple from a screenplay by Oscar winner Stephen Gaghan (Traffic), the film chronicles the travails of two rich white girls from Beverly Hills (Hathaway and Bijou Phillips) who act black and eventually get mixed up with menacing Latino gang members in East L.A. The film, which also stars Joseph Gordon-Levitt and features a brief appearance by Channing Tatum—in his first film role—sees Hathaway rapping along to Tupac and Jay-Z, smoking crack, and throwing haymakers. You will laugh your ass off.
Hugh Jackman: Movie 43 (2013)
Oscar Nomination: Best Actor, Les Misérables
Hathaway’s Les Miz savior, Hugh Jackman, has his first Oscar nomination in the best-actor category for his courageous turn as wanted man cum aristocrat Jean Valjean in the movie-musical. And while Jackman is every bit deserving of the nod, he does have some patchiness on his résumé, including the sex-club thriller Deception and one of the worst Woody Allen films ever, Scoop. But the debacle that is Movie 43 takes the cake. In this series of “comedy” vignettes spearheaded by the Farrelly brothers, Jackman plays a man whose blind date, played by Kate Winslet, is disgusted to learn that he has a pair of saggy balls protruding from his throat (yes, really). The film, released smack-dab in the middle of this year’s awards season, had been called one of the worst films of all time by a slew of critics.
Jennifer Lawrence: Monk episode “Mr. Monk and the Big Game” (2006)
Oscar Nomination: Best Actress, Silver Linings Playbook
Jennifer Lawrence is, without question, one of the finest and most naturally gifted young actors around today and earned a well-deserved second Oscar nomination for her turn as a depressed widow and recovering sex addict in David O. Russell’s ensemble dramedy Silver Linings Playbook. And while she admitted to starring in an embarrassing commercial for the MTV show My Super Sweet 16 in order to get her Screen Actors Guild card, her turn as an aggressively cheery high school basketball mascot in the episode “Mr. Monk and the Big Game” during the fifth season of the TV series Monk is even funnier. She shows a whole lot of school spirit, dancing like crazy on the sidelines and even jumping on Monk’s back.
Philip Seymour Hoffman, My Boyfriend’s Back (1993)
Oscar Nomination: Best Supporting Actor, The Master
In Paul Thomas Anderson’s The Master, Philip Seymour Hoffman delivers a riveting performance as the conflicted bullshit artist—er, “mystic”—Lancaster Dodd, who takes a troubled World War II Navy veteran, played by Joaquin Phoenix, under his wing. The role earned him his fourth Oscar nomination (he won best actor in 2006 for Capote). While Hoffman is regarded as one of the finest actors around, his turn as a demented school bully in Bob Balaban’s cult horror flick My Boyfriend’s Back is pretty embarrassing. The film, oddly enough, also features early performances by Matthew McConaughey and Matthew Fox, and Renée Zellweger filmed a scene for it as well—that was left on the editing room floor.
Amy Adams, Cruel Intentions 2 (2000)
Oscar Nomination: Best Supporting Actress, The Master
Following the success of Cruel Intentions, one of the more effective, titillating films to emerge from the “let’s transform a classic work into a high school dramedy” era in the late 1990s, a spinoff TV series called Manchester Prep was set to air on Fox. The series proved too racy for Fox execs, who canceled it before it ever premiered. But then, in a truly shameless, sinister act befitting the film’s Machiavellian antagonist, the three episodes shot were edited into a direct-to-video prequel released in 2000. The femme fatale, Kathryn Merteuil (Amy Adams), is a rich-bitch teen who mercilessly toys with Sebastian Valmont, played by direct-to-video sequel star Robin Dunne (see: The Skulls II, Species III, American Psycho II: All American Girl). Other than a fleeting scene where Kathryn’s mother berates her, Adams’s character is a remarkably one-dimensional hussy. It wasn’t until Adams’s Oscar-nominated turn as a cheery, heavily pregnant Southern gal in the 2005 Sundance hit Junebug that she seemed to fully embrace her immense likability. And she hasn’t looked back since.
Joaquin Phoenix, I’m Still Here (2010)
Oscar Nomination: Best Actor, The Master
Joaquin Phoenix delivered, in my estimation, the best performance by a male actor in 2012 as unhinged, paint-thinner-swilling, disillusioned World War II Navy vet Freddie Quell in The Master. It’s as feral and unpredictable a turn as has ever been put to screen. But The Master was actually a comeback role for Phoenix, who last appeared in the 2010 mockumentary I’m Still Here. For the film, in which he feigned quitting acting to become a rapper, the actor packed on nearly 40 pounds, grew a hideous beard, and appeared to be on serious, slur-inducing meds. In the movie, he is seen being defecated on by his friend, snorting cocaine, receiving oral sex from a hooker, and just acting like an all-around ass. At one point, he even calls Obama’s 2008 inauguration ceremony “a movie premiere with less pussy.” Of course, none of this was real, and it was all in the name of “art.”
Bradley Cooper, All About Steve (2009)
Oscar Nomination: Best Actor, Silver Linings Playbook
Bradley Cooper gives his most thrilling, multidimensional performance to date as Pat Solitano, a grieving ex-husband struggling with bipolar disorder in David O. Russell’s Silver Linings Playbook, earning him his first Oscar nomination. Prior to Cooper’s breakout turn in 2009’s The Hangover, it took him quite a while to ascend to leading-man status, and thus, his résumé is peppered with some regrettable choices. There’s the direct-to-video flick I Want to Marry Ryan Banks, in which he co-stars alongside Jason Priestley as an exec who creates a reality dating show for the 90210 alum, and also his brief stint as douche-bag attorney Jason Whitaker on Law & Order. But it’s All About Steve, one of the worst films of 2009, that is his most embarrassing. Cooper stars as Steve Miller, a TV-news cameraman who becomes the object of Mary’s (Sandra Bullock) bizarre affections, as she stalks him around the country. The film won two Razzie Awards for Worst Actress (Bullock) and Worst Screen Couple (Bullock and Cooper), and the very next day, Bullock picked up the Oscar for best actress, becoming the first actor ever to win an Oscar and a Razzie in the same year.
Naomi Watts, Children of the Corn: The Gathering (1996)
Oscar Nomination: Best Actress, The Impossible
Naomi Watts’s decade-long struggle to break into Hollywood has become the stuff of legend. The Aussie would drive from audition to audition in her beat-up car, only to be shot down on the regular. Before auteur David Lynch came across her headshot and cast her in 2001’s Mulholland Dr., Watts undertook a bevy of regrettable jobs during her darker years, the most unfortunate of which is the straight-to-video horror flick Children of the Corn IV: The Gathering. Watts plays a medical student who returns to her hometown in rural Nebraska to discover that the local children are becoming possessed, transforming into demonic killing machines. So naturally, Watts has to bludgeon some killer kids. “I was in Children of the Corn IV or V, and got paid $5,000 to do that whole film, but so what?” Watts told The Daily Beast. “In retrospect, I would have loved to have had more time in my 20s playing different roles, but maybe I would’ve gone off course or got seduced into doing things I wasn’t good at. It was the right way.”
Tommy Lee Jones, Man of the House (2005)
Oscar Nomination: Best Supporting Actor, Lincoln
Despite his memed stone-faced expression at this year’s Golden Globes, Tommy Lee Jones is a gifted comedic actor, with his dry turns in the Men in Black flicks and his sassy, motormouth FBI agent in The Fugitive. But the crime comedy Man of the House, released in 2005, was a major misfire. Jones stars as a lonely Texas Ranger who goes undercover as a cheerleading coach to protect a group of college cheerleaders who witnessed a murder. In the film, Jones tackles a water-gun-wielding mascot, goes skating, and delivers an impassioned speech about cheerleading. Plus, one of the college girls he’s protecting even develops a crush on him, and to make matters worse, the movie features a cameo by Texas Gov. Rick Perry. Ugh.
Robert De Niro, Red Lights (2012)
Oscar Nomination: Best Supporting Actor, Silver Linings Playbook
Screen legend Robert De Niro scored his first Oscar nomination in 21 years—since 1991’s Cape Fear—for his role as an OCD football nut and loving father in Silver Linings Playbook. In the 21st century, De Niro, one of the greatest actors ever, has made many puzzling film choices, from 2000’s The Adventures of Rocky and Bullwinkle to 2011’s ensemble calamity New Year’s Eve. But it’s last year’s truly awful thriller Red Lights that provides the platform for arguably his most regrettable turn. De Niro plays Simon Silver, a blind psychic who’s being tracked by paranormal investigators who believe he’s a fraud. But the investigators, led by Cillian Murphy, start to believe that maybe he’s the real deal when strange things start happening to them—dead birds appearing, loud explosions, etc. De Niro’s psychic “performances,” meanwhile, are truly a sight to behold ... and not in a good way.