If you want to go back in time, there are actually 6 actors who have accomplished this hallowed double award winning honor. Bing Crosby (1944) won for “Going My Way” and we all know Bing’s biggest selling Christmas song of all-time, but this was before the modern Billboard era. Then you have Frank Sinatra (1953) who won Best Supporting Actor for “From Here To Eternity”. Will Smith has been nominated for Best Actor (Ali and The Pursuit of Happyness) but has yet to win the Oscar. Mark Wahlberg hit #1 with the Funky Bunch and got a nod for “The Departed” in the Best Supporting Actor category. But in the last 25 years, who are the only 3 to WIN Best Actor or Actress and score a Top 5 hit? John Travolta and Richard Harris both got nominations and had a music hit but did not meet the criteria.
2004 JAMIE FOXX For “Ray”
1987 CHER For “Moonstruck”
1968 BARBRA STREISAND For “Funny Girl”