[4] "You Can't Win" was originally written and performed during the pre-Broadway Baltimore run of the stage version of The Wiz in 1974, sung by the chorus of Winkies, the Wicked Witch's slaves.

William F. Brown, who wrote the book for the Broadway musical, stated that such verses made "You Can't Win" a "black message song".

[8] The scene that corresponds with "You Can't Win" in The Wiz begins with Dorothy Gale (played by Diana Ross) stumbling upon a scarecrow being heckled by crows while stuck in the air on a pole.

Elwood Watson, author of Pimps, Wimps, Studs, Thugs and Gentlemen: Essays on Media Images of Masculinity, states that The Wiz offers an "important allegorical treatment of ordinary African American men living in the wake of the Civil Rights Movement".

Watson writes that while the crows do not intend to cause physical harm to Scarecrow, the beginning of their scene recalls experiences of the ritual lynching of black men in the United States.

The author states that the crows' refusal to allow Scarecrow to read literature was reminiscent of laws that forbade black slaves from being educated.

The Crows reinforce Scarecrow's subjection at their hands through a song whose refrain "you can't win child, you can't get out of the game" that aims to disabuse Scarecrow of any aspirations toward freedom ... Their insistence that "reading is stupid" suggests that a Eurocentric education does not promise liberation from "the game" that race and racism create ...

[11] Watson continued his analysis, writing that despite the crows' attempts to erode Scarecrow's confidence, "[he] gives no indication that he intends to abort his efforts to liberate himself physically and intellectually."

"[11] 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.

[12][13] 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.

[19] 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.

"[7] 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".

[21] Margo Jefferson wrote in the biography On Michael Jackson that the entertainer sang the song in the film with "rough, gospel edges of desperation".

[24] In 2003, during the second season of American Idol, contestant Charles Grigsby sang "You Can't Win" for a movie theme night.

[27] Decades after the release of "You Can't Win", William F. Brown stated that the song had been dropped from his theater productions of The Wiz.