For a man typically of few words, Prince had something to say when he appeared on CNN's Larry King Live on Dec. 10, 1999.
In an interview that spanned an hour's worth of programming, The Artist (then-known by his unpronounceable symbol) met with the suspender-clad broadcaster to discuss everything from creative freedom and spiritual beliefs to his artistic approach and a planned concert at his Paisley Park recording studio, where - just weeks before the end of the millennium - he planned to retire his prophetic hit single "1999."
"I never felt like this was going to be a rough time for me," he told King amid anxieties over Y2K. "I just wanted to write something that gave hope, and what I find is people listen to it. And no matter where we are in the world, I always get the same type of response from them."
The Artist, who had just released the album Rave Un2 The Joy Fantastic, was also joined by friend Larry Graham, bassist for Sly & The Family Stone. "I've worked with other musicians that were great, but they didn't allow me to really have the freedom that I needed to be able to give them all that I could give them," Graham said warmly of Prince. "With baby brother, he allows me the freedom...and as a result, what we're doing now, when you hear it, you can see that it's coming from the heart."
After Prince's passing in 2016, King recalled his kindness during their time together. "He had a sensitivity next to no one," King told NBC. "I never saw anyone as warm, tender and sweet as he was."