Release and Reception
In January 1979, "You Can't Win" was released as the second single from The Wiz: Original Motion Picture Soundtrack, a double album distributed by Motown Records in September 1978. The single was issued after the September 1978 release of "Ease on Down the Road", a duet between Jackson and Diana Ross, who played protagonist Dorothy Gale in The Wiz. "You Can't Win" was distributed under Epic Records, and was Jackson's first solo single issued by the company after Epic executives signed him and his brothers to the label in 1976. "You Can't Win" entered Billboard's R&B singles chart on January 20, 1979. It reached number 42 and remained in the chart for ten weeks. A month later, on February 24, 1979, it entered the Billboard Hot 100, where it peaked at number 81. The single stayed in the chart for three weeks. In May 1979, "You Can't Win" was released in Britain, as was a 7" picture disc of the song. The single failed to enter the British charts. When Jackson's Off the Wall was first released in August 1979, the picture disc supplemented the album.
Since its release, "You Can't Win" has received positive reviews from music critics. A journalist from the Kansas City Star said that the song was the best one from The Wiz. Kenny Mack of the Santa Monica Daily Press asserted that Jackson's "famous vulnerability and the power of his voice on 'You Can't Win' combined for perfect casting" in the film. The Boston Globe's Renée Graham stated in 2005, "Halfway through the, Jackson lets out a whoop, and the tune evolves from a pop-soul confection into a true R&B delight, spiced with barking horns and hand-claps as funky and loose as anything Jackson has ever done." Writer Geoff Brown wrote in his book Michael Jackson: A Life in Music that the singer's performance of "You Can't Win" in The Wiz was "one of the few bright moments in a drab remake of The Wizard of Oz". Margo Jefferson wrote in the biography On Michael Jackson that the entertainer sang the song in the film with "rough, gospel edges of desperation". She added, "The torment feels genuine. It's a painful scene." After Jackson's death in 2009, Edmund W. Lewis of The Louisiana Weekly said that he was "still amazed at the quality of 's performance in The Wiz". He added, "As the scarecrow, he sang the hell out of ."
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