Notorious box-office bomb Heaven’s Gate was nominated for an Oscar and won Worst Director in the Razzies, but I don’t know of any movie that was won at least one of each.
My corporate filter blocks the Razzies site. Weird. Anyway, I’d bet some special-effects extravaganza has won technical Oscars while still getting a Razzie. Did any of the stars of Star Wars I-III win a Razzie?
Some actors have: Lawrence Olivier, Roberto Benigni, Liza Minnelli, Halle Berry
It’s less likely that a film wins both, or is even nominated by both, since anything that might be considered for an Oscar is probably not so obviously awful that it would get a Razzie.
Norbit is up for something in the Razzies this year and is also up for a makeup award at the Oscars, so this could be the year!
There are definitely some of your more over the top acting performances that walk a fine line between Oscar worthy and Razzie worthy- I personally felt Halle Berry’s acting in Monsters Ball was hilarious (make me feel good, especially), and razzie worthy, but Oscar voters felt different. Heath Ledger was great in that though.
Screenwriter Brian Helgeland had the distinction of winning an Oscar (L.A. Confidential) and a Razzie (The Postman) in the same year.
Other Razzie winners with Oscar nominations: The Addams Family (and its sequel), Annie, Armageddon, Beverly Hills Cop II, The Blue Lagoon, Con Air, Gloria, The Godfather Part III, Harlem Nights, Honeysuckle Rose, Interview with the Vampire, Poetic Justice, Rambo: First Blood Part II, Robin Hood: Prince of Thieves, Sunset, Twister, Waterworld, Wyatt Earp, and Star Wars Episodes I-III (all 3 installments). Plus, Norbit has a very good chance of joining that group this year.
But you’d have to go back to 1986 to find the only film that answers the OP: Wall Street won an Oscar for Michael Douglas (Best Actor) and a Razzie for Daryl Hannah (Worst Supporting Actress).
It might have happened this year. Razzies release longlists prior to their nominations, to indicate their semi-final results. In this year’s Worst Actress longlist, Cate Blanchett was up for Elizabeth: The Golden Age, which also got an Oscar nomination. But when the Razzie nominations were announced the day before the Oscar nominations, Cate wasn’t one of the final five. She’s not going to win the Oscar anyway, but still it was funny to see the same performance on both lists.
Razzies had a bunch of former Oscar winners in their longlists this year. Halle Berry, Cate Blanchett, Nicole Kidman, Hilary Swank and Diane Keaton. Diane was the only one who made it to the finals. Here are the nominations, including the longlists.