Eminem: Eminem starred in his seminal biopic '8 Mile' released in 2002. The rapper produced and sang the rap 'Lose Yourself' with Jeff Bass and Luis Resto. During the 75th Academy awards, the song won the trophy.
Billie Eilish and Finneas O'Connell: If you are creating the soundtrack for 007, those are the tough shoes to fill. But, Billie Eilish and Finneas not only created a ballad for 'No Time To Die'. they also won an Oscar for that.
Elton John: The Oscar maverick Elton John got his second Oscar in 2020 for '(I'm Gonna) Love Me Again' for his biopic 'Rocketman'. He won the award along with his longtime associate Bernie Taupin. He won his first Academy for 'The Lion King' in 1995
Bob Dylan: For 'Things Have Changed' from 'Wonder Boys', Bob Dylan won his first Oscar in 2001. It was the most unexpected win of the night.
Lady Gaga: The singer got her first Oscar nomination as an actress for 'A Star Is Born' starring Bradley Cooper. However, Lady Gaga took the trophy during the 2019 Academy Awards for the love ballad 'Shallow'.
Bruce Springsteen: The rock 'n' roll artist won the award for Tom Hanks starrer 'Philadelphia'. He rendered his vocals for the song 'Streets of Philadelphia'. He became the first rock 'n' roll artist to won an award in 'Best Original Song' category.
Stevie Wonder: At the 57th Academy Awards, Stevie Wonder took the trophy for his heartbreak song from the movie 'The Woman In Red' titled 'I Just Came To Say I Love You'.
Prince: In 1985, Prince, in his signature flamboyant look donning a purple, sequinned dress arrived at the Oscars. He released in 1984 a musical and album titled 'Purple Rain'. He wanted to dabble into the rock 'n' roll space. In a rare scenario, he won the award in 'Best Original Song Score' category.