Which singer made the most successful transition to acting?

Bing Crosby. Not only was he the most successful recording artist of the th century, he also was the originator of the modern pop singing style which was only possible with the introduction of amplification and the microphone. Sinatra, who featured in only about movies, based his singing style on Crosby’s innovative style.

Crosby acted in over movies, was nominated for the Oscar three times and won for Best Actor once.

I’d guess that it’s Frank Sinatra.

Also some other interesting ones: most know Minnie Driver as an actress, not the singer she was before she started acting. Also, there’s Barbra Streisand.

I think in recent times Wil Smith has done a pretty good job with that transition.