Prince always maintained a cautious eye towards the media. He rarely gave interviews and generally tried to distance himself from any attention he deemed unnecessary.

So, when Prince agreed to appear on The Oprah Winfrey Show on Nov. 21, 1996, it marked a rare chance for fans to get a behind-the-scenes glance at his life. Looking back through more than two decades of hindsight, the appearance is both historic and heartbreaking.

The majority of Prince’s interview with Oprah was pre-recorded, shot several weeks prior when the talk show host visited Paisley Park. Initially, their conversation focused on the singer’s name change, one of the most discussed pop-culture topics of the time.

“What do I call you?,” Oprah asked, alluding to the unpronounceable symbol that was now Prince’s moniker. “Friend, I hope,” the singer answered, flashing a sly smile after giving his response.

“Just like Muhammad Ali and Malcolm X, people like that change their name,” Prince went on to explain. “And some people take names that are hard to pronounce. It just so happened that I took one that you can’t pronounce.”

Later, Paisley Park staff admitted they called him anything from “Sir” to “Boss” and even “Bro.”

As the interview continued, Prince’s wife Mayte Garcia joined the conversation. The two had married earlier that year at a private ceremony on Valentine’s Day. Oprah spoke to the couple about their relationship, their courtship and how love has affected Prince’s life. “I’ve come closer to who I aspire to be by being with her,” Prince said to Garcia.

The topic then turned to the couple’s child, who had been born just a few weeks prior. Oprah noted that rumors of health problems had fans concerned, but Prince insisted that things were “all good.” “Our family exists," he added. "We’re just beginning it. And we’ve got many kids to have and a long way to go.”

Watch Prince on 'The Oprah Winfrey Show'

Sadly, fans later discovered that Prince was putting on a tough facade. Their son Amiir had been born with a rare genetic disorder, and died weeks before the taping with Oprah. Prince, however, was determined to keep this awful news under wraps.

“I sat on the sofa, smiling a pretty ballerina smile. I’d been instructed by my husband, ‘Say nothing about Amiir,’” Garcia recalled many years later in her memoir, The Most Beautiful: My Life With Prince.

Whether keeping up the charade, or simply dealing with his own state of denial, Prince later showed Oprah the nursery he’d had built at Paisley Park. Its existence surprised Garcia, who was unaware of the room’s creation.

“Oprah saw it before I did,” Garcia wrote in her book. “I have to wonder why he took her in there. They stood in the middle of this colorful paradise of toys. It had everything a perfect nursery needs, except for the only thing a perfect nursery needs.”

Prince’s conversation with Oprah continued one-on-one from there, delving further into his fascinating life. He was candid discussing his childhood, admitting he was bullied for his small stature and even created an internal second persona to deal with the abuse. “That’s probably when that person got created,” Prince explained. “Somebody to care about you, love you and be your friend, and not ridicule you.” Throughout the conversation, he displayed a vulnerability rarely seen by the public.

Though the majority of the program’s material was filmed at Paisley Park, Prince did appear in Oprah’s television studio to deliver several emphatic live performances. The first set of the day featured a soaring, sultry rendition of "Do Me, Baby," followed by the funked-out beats of "If I Was Your Girlfriend." Toward the end of the show, Prince returned to deliver the high-energy dance track "Sleep Around."

As the episode was coming to a close, Oprah asked Prince one final question – the only one delivered live in front of the studio audience. “How many more songs do you think you have inside yourself?,” she inquired. Prince, perhaps caught a little off guard, smiled and responded: “One a day... until I die.”
 
 

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