From Oscar To Flop: When Award-Winning Movie Roles Are Followed By Duds

For some odd reason, well-respected Hollywood actors have a habit of taking mediocre and sometimes awful roles right on the heels of Oscar-nominated performances. Natalie Portman, the fox with bedhead in the movie poster above, is the latest example. Her role in the grating rom-com “No Strings Attached” follows her insanely intense performance in “Black Swan.” She’ll probably win an Oscar for “Black Swan,” while “NSA” will be lucky if it wins the box office. Maybe it’s your cup of tea, but I can think of about 47 better ways to spend a Friday night, a third of which end with an empty box of bagel bites.

Sometimes actors are lucky enough that theirs come out after they’ve won an Oscar. The unlucky ones have the poorly timed releases come out just before Academy Award nominations are announced. In both cases, the crappy films are typically “paycheck” movies, and while it’s hard to blame someone for trying to get paid, that’s exactly what we’re about to do.

2. Justin Timberlake

The Big Role: JT delivered a solid performance in one of 2010′s biggest films, “The Social Network,” and there’s some speculation that he might get an Oscar nod for best supporting actor.

The Follow-up: Were you able to spot him in the picture above? I think he’s the bear in the middle. Sure, it’s a nice kids movie that probably came with a fat paycheck…but probably not a role (he voiced Boo-Boo) that will endear him to stuffy Academy voters.

Flop-O-Meter: The film has a 15 percent Tomato rating. Hey, Boo-Boo!

3. Sandra Bullock

The Big Role: Sandra’s performance in “The Blind Side,” which came out in November 2009, earned her an Oscar for best actress.

The Follow-up: Not quite a follow-up because it came out at about the same time, but Sandra’s role as an umbrella-wielding happy person in “All About Steve” boasts (?) a shocking 6 percent Tomato rating and won her a Razzie award for worst actress.

Flop-O-MeterSandra accepted the Razzie award in person and later won the Oscar, making her the only person to win both a Razzie and an Oscar in the same year.

4. Cuba Gooding Jr.

The Big Role: Cuba won best supporting actor for his outstanding job as Rod Tidwell, an excitable wide receiver he played in “Jerry Maguire.”

The Follow-up: Granted, Cuba appears to be having an amazing time in “Boat Trip,” in which he and Horatio Sanz accidentally end up on a cruise for gay men, but the film was an abject disaster. He’s had some nice roles since (“American Gangster”), but Gooding Jr.’s career obviously peaked, to date, with “Jerry Maguire.”

Flop-O-Meter: Here’s the sad thing: Anyone born after 1996 would probably know Cuba best as the guy in awkward underwear commercials with Michael Jordan.

5. Anne Hathaway

The Big Role: Anne was nominated for best actress for her role in the family and wedding-themed drama “Rachel Getting Married.”

The Follow-up: Her first role following “Rachel Getting Married” was in another wedding-themed movie, “Bride Wars,” released in January 2009. It looks like a dressed-up extended of version of “Bridezillas,” which sounds like a horrible waste of $11.25, two hours and Anne’s talent.

Flop-O-Meter: The film nudged into double digits with an 11 percent Tomato rating. At the Oscars, Anne lost out to Meryl Streep, who won the statue for best actress for her performance in “Doubt.”

6. Robin Williams

The Big Role: Robin Williams was nominated for three Academy Awards for best actor (“Good Morning, Vietnam,” “Dead Poets Society” and “The Fisher King”) before finally winning for best supporting actor for his performance in “Good Will Hunting.”

The Follow-up: Williams has been in some good flicks in the years since “Good Will Hunting,” but he’s been in some pretty awful movies too. Including, “License To Wed,” “Man Of The Year” and “RV.”

Flop-O-Meter: Carrie Rickey of the Philadelphia Inquirer described “RV” as “[a]bout as funny as an explosion in a septic tank.” Ouch.

7. Alec Baldwin

The Big Role: Nominated for best supporting actor for his role in the old-school casino drama, “The Cooler.”

The Follow-up: Baldwin has had a long, illustrious career, so no one reasonable could really hold any bad film against him, but the timing of “The Cat In The Hat” was not ideal for someone wanting to win an Oscar.

Flop-O-Meter: The Dr. Seuss film was widely panned and Baldwin did not win the Oscar. Somewhere, Canteen Boy became disappointed.

8. Eddie Murphy

The Big Role: In 2007, Eddie was nominated for best supporting actor for his role in the based-on-a-Broadway-musical “Dreamgirls.”

The Follow-up: Eddie did his multicharacter dress-up routine (Semmi, look at this!) for this cinematic disaster about a dorky dude who falls in love with an extremely large woman. Incredibly, the actual tag line for the movie, which hit theaters in February before the Academy Awards ceremony, was “Have you ever made a really big mistake?”

Flop-O-Meter: A mistake indeed. Eddie did not win the Oscar.

9. Halle Berry

The Big Role: Halle won best actress for her performance in “Monster’s Ball.” The same film where she had uncomfortable onscreen sex with Billy Bob Thornton. The same Billy Bob Thorton who did this.

The Follow-up: Everything, and I repeat, everything was right with Halle’s Catwoman costume, it’s just that the movie stunk. Comic book fans also griped that “Catwoman” barely used the source material.

Flop-O-Meter: You keep looking back at the photo above, don’t you? Understandable. The role got Halle Berry a Razzie award for worst actress, which she accepted with her Oscar in hand.

10. Matt Damon

The Big Role: Damon was nominated for best actor and best screenplay for ”Good Will Hunting,” and he won for the writing along with Ben Affleck.

The Follow-up: Damon’s acting résumé is long and studded with hits (e.g., the Bourne trilogy), so he’s entitled to take some goofy roles. It’s just that “Stuck On You” was…bad. Or in other words, not good.

Flop-O-Meter: He’s done just fine for himself, but this one really stands out as the dud.

Photos: Universal Pictures, 20th Century Fox, Getty Images