Has it ever happened? It’s plausible “Lone Ranger” could win the Makeup/Hairstyling Oscars, and it has a bunch of nominations at the Razzies. I know several Razzie films have been nominated for technical Oscars, but how many (if any) films have won something at both awards?
I believe “Barry Lyndon” won worst picture from the pre-cursor to the Razzie Awards ,I believe it was called the National Lampoon Award, while being an Oscar nominee for best pcture and winning awards for cinematography, art direction, score and costume design.
Other films have been nominated for both in the past although in different categories: Robin Hood, Armageddon, Norbit. But I think Wall Street is the only film to have won both a Razzie and an Oscar. Douglas won the Oscar, Darryl Hannah won a richly deserved Razzie.
The Razzies now go after a lot of low hanging fruit (Sandler, Stallone). They used to attack more prestigious pictures that were critical bombs. I think two actors were nominated for both the Razzie and the Oscar for their performances, Amy Irving and James Coco. Irving is terrible in Yentl, but I actually quite liked Coco in Only When I Laugh, which also contains Marsha Mason’s best performance. Too bad it is never seen nowadays.