Frank Sinatra had some frank words for a young, fame-weary George Michael back in 1990: “Loosen up. Swing, man.”

Known more for his quips on the joys of drinking than salient career advice, Sinatra’s input on Michael’s nascent celebrity was equal parts pep-talk and fatherly chiding. “Dust off those gossamer wings and fly yourself to the moon of your choice,” he wrote, “and be grateful to carry the baggage we’ve all had to carry since those lean nights of sleeping on buses and helping the driver unload the instruments.”

At the time, Michael was suffering from sophomore-album cold feet. In the lead up to the release of the Wham! singer’s sophomore album, “Listen Without Prejudice Vol. 1,” he had become media shy, perhaps because he had a lot to live up to: His 1987 solo debut three years earlier, “Faith,” had won a Grammy, spawned six top-five singles, and went on to sell more than 25 million records.

In comparison, his second record was a comparative flop in the US, selling only 2 million copies. (It had a better reception in his native UK, but total sales were less than a third of “Faith.”) During this time, Michael eschewed the spotlight, gave very few interviews, and didn’t tour the album—all equivalents of PR suicide.

In Sept. 1990, the LA Times’ Calendar Magazine published an article, “George Michael’s Case Against Fame,” which didn’t cast the singer in a particularly glowing light. ”To a cynical pop world that has heard everyone from Frank Sinatra to David Bowie threaten to say goodby [sic] to the microphone,” reads the article, “the latest vows of George Michael may seem like little more than a calculated publicity move. After all, he’s obviously still doing interviews.”

Likely stirred by the reference to his own moments of professional introversion—Sinatra had his own bouts of self-doubt, announcing his retirement in 1971 before going on to play a further 1,000 shows—he published an open letter to Michael in the same magazine the following week, imploring him to pull his head out:

In it, he instructs Michael to understand the importance of heeding the audience’s wishes, telling him that to have such an ability is a curse that must be shared, not squandered: “Talent must not be wasted… those who have talent must hug it, embrace it, nurture it and share it lest it be taken away from you as fast as it was loaned to you.”

“Trust me. I’ve been there.”

The full transcript follows: