“The Man” is the second of McCartney’s three collaborations with Michael Jackson, recorded in 1981 and released on Pipes of Peace (1983).
Jackson wrote the lyrics, about some wise dancing man who “plays the game of life so well.” McCartney wasn’t sure if Jackson was talking about Jesus or a Jehova’s Witness — or just a happy “fool on the hill” type guy who kicked up his heels like The Wiz — but went with it.
So it was the second song McCartney sang that seemed to be a merry ode to the general wisdom of “The Man” (the other being “Listen to What the Man Said”), apparently unaware that to many “The Man” was slang for an oppressive government/authoritarian figure. Jackson, too, was apparently unaware or unconcerned.
With two hit singles under their belt (“Say Say Say” and “The Girl Is Mine”), it seemed they had a good thing going. But then McCartney advised Michael Jackson to start buying song copyrights to make big money. Around that time, ATV Music Publishing went up for sale. It owned the copyrights to most of the Lennon/McCartney songs, and as a courtesy they offered McCartney the option to buy it for $40 million. McCartney tried to get Yoko Ono (who ran Lennon’s estate) to split it with him, but she thought they could get it for $20 million. When that deal didn’t happen, McCartney decided to drop it because it was “too pricey.”
So in 1985, Michael Jackson bought it for $47.5 million. Even though he had originally passed, McCartney was reputedly unhappy about it, and they never worked together again.