Cuba Gooding, Jr., Best Supporting Actor for “Jerry Maguire” (1996)
Remember “Show me the money?” So charming, so loud. That was Cuba Gooding, Jr., as a hotshot football player in Cameron Crowe’s amiable comedy/drama “Jerry Maguire.” Unfortunately for Gooding, Jr., he followed his win with a slew of box office duds, including “What Dreams May Come,” “Instinct,” “Chill Factor,” “Rat Race,” Snow Dogs,” “Boat Trip,” and “The Land Before Time XIII: The Wisdom of Friends,” playing a dinosaur named Loofah.
Adrien Brody, Best Actor for “The Pianist” (2003)
Adrien Brody gave a genuinely brilliant, devastating performance in Roman Polanski’s autobiographical World War II tearjerker “The Pianist.” But since then? Well, he’s been saddled in increasingly lowbrow fare. Some of his post-Oscar-win decisions probably seemed like good ideas at the time (a “King Kong” remake from Peter Jackson; the new film by then-unstoppable M. Night Shyamalan; some movie with Wes Anderson and a train) but all turned out to be duds.
Jennifer Connelly, Best Supporting Actress for “A Beautiful Mind” (2002)
Up until her Oscar win, Jennifer Connelly had a solid and somewhat varied career, appearing in Jim Henson’s nightmare puppet show “Labyrinth,” the pulpy throwback “The Rocketeer,” and druggy drama “Requiem for a Dream.” But after her Oscar win, her career has been a mixed bag. Her first big role post-Academy Award was in Ang Lee’s misunderstood “Hulk,” which led to her veering back towards more prestige fare like the overwrought melodrama of “House of Sand and Fog,” “Reservation Road,” and “Blood Diamond.” Her attempts at mainstream success resulted in equally iffy product, including the “Ring” rip-off “Dark Water” and the disastrous “Day the Earth Stood Still” remake.
Brenda Fricker, Best Supporting Actress for “My Left Foot” (1990)
This is a testament to how much of a blip Fricker’s Best Supporting Actress win for “My Left Foot” was: less than three years later she would have a supporting role as the misunderstood woman covered in pigeons in “Home Alone 2: Lost In New York.” Fricker still works steadily, though without much fanfare. Additional roles include inglorious turns in “Angels in the Outfield,” “So I Married An Axe Murderer,” that strange Robin Wright version of “Moll Flanders,” and an after-the-fact 2004 TV movie about Heidi Fleiss entitled “Call Me: The Rise and Fall of Heidi Fleiss.”
Bruce Joel Rubin, Best Original Screenplay for “Ghost” (1991)
Sure, “Ghost” was a great screenplay. (And, yes, the same year as “Ghost,” Rubin wrote the even-more-brilliant “Jacob’s Ladder.”) But afterwards his career more or less stalled, as he turned in workmanlike scripts for “Stuart Little 2,” “Deep Impact,” the maudlin “My Life” (which he also directed), and “The Last Mimzy.” By 2011, he was writing the book and lyrics to the musical version of “Ghost.”
Roberto Benigni, Best Actor for “Life is Beautiful” (1999)
Oh, Roberto Benigni! He was so charming! He wanted every member of the Oscar audience to love him! And then … very little. Afterward he appeared in an adaptation of a European comic book that still hasn’t seen stateside distribution, and then decided, at the tender age of 50, to star in an adaptation of “Pinocchio,” playing the title character. The movie, one of the costliest in the history of European cinema, was such a box-office disaster in America that his following film, “The Tiger and the Snow,” which tried to put a tragic-comic spin on the Iraq War, was barely released here. Benigni did show up, charmingly, in last year’s Woody Allen trifle “To Rome With Love,” but it was fleeting, not enough to remind anyone why he was so beloved in the first place.
Mercedes Ruehl, Best Supporting Actress for “The Fisher King” (1992)
This might be the best example of winning an Oscar and then disappearing completely. Her first two post-win roles were in a poorly received adaptation of Neil Simon’s “Lost in Yonkers” and “Last Action Hero,” the notorious action-comedy hybrid starring Arnold Schwarzenegger that opened up against “Jurassic Park” and turned out to be one of the biggest flops of all-time. Since then, she’s been quiet, appearing in only three movies since 2004.
Timothy Hutton, Best Supporting Actor for “Ordinary People” (1981)
Although “Ordinary People” managed to trump Martin Scorsese’s groundbreaking “Raging Bull” in the Best Picture category, Hutton’s win holds a special distinction: He remains the youngest ever actor to win a Supporting Oscar. It’s pretty amazing, considering that earlier in the year he was starring in an episode of “Disney’s Wonderful World” entitled “The Sultan and the Rock Star.” Since then, he’s mainly stuck to bit parts in small feature films and made-for-TV movies.
Joel Grey, Best Supporting Actor for “Cabaret” (1972)
This Oscar win sticks out, mainly for who Grey won Best Supporting Actor over: James Caan, Robert Duvall, <em>and</em> Al Pacino for “The Godfather.” While Grey remains active on Broadway, he has had only a couple of additional noteworthy roles since then. He directly followed his Academy Award win with twin disasters, Robert Altman’s indescribably odd “Buffalo Bill and the Indians, or Sitting Bull’s History Lesson” and “Remo Williams: The Adventure Begins,” which also sputtered.
Michael Cimino, Best Director for “The Deer Hunter” (1979)
Few falls from grace are more tragic than Michael Cimino, a universally acclaimed auteur for his Best Picture/Best Director-winning “The Deer Hunter,” who would quickly become a punch-line and pariah within the industry. The reason? He took all his cache and decided to funnel it into a single passion project: a three-hour-plus epic loosely based on the Johnson County War. “Heaven’s Gate” would become an infamous example of a wildly creative talent-turned-tyrant, and a financial flop so massive that nearly caused United Artists to close down its doors for good. Cimino’s output following the initial release proved even more dire, with things like the half-hearted Mario Puzo adaptation “The Sicilian” and “Sunchaser.”