Larry King, a giant in the broadcast journalism world, died on Saturday, January 23rd at the age of 87 after having been hospitalized for COVID-19 in December.

A nightly staple on CNN for decades, the ever-earnest King, in his trademark suspenders and thick-rimmed glasses, became a singular voice in the broadcast world known both for convincing the most interesting and influential figures from every corner of society—oftentimes, those who typically shied away from interviews—to appear on television and getting them to open up on camera.

As The Associated Press noted in its obituary for Larry King, “King conducted an estimated 50,000 on-air interviews. In 1995 he presided over a Middle East peace summit with PLO Chairman Yasser Arafat, King Hussein of Jordan and Israeli Prime Minister Yitzhak Rabin. He welcomed everyone from the Dalai Lama to Elizabeth Taylor, from Mikhail Gorbachev to Barack Obama, Bill Gates to Lady Gaga.”

Explained Associated Press Institute executive director Tom Rosenstiel, “King was one of the few people in broadcast history who basically created his own phenomenon. He didn’t need a network. The network needed him … He coaxed, rather than challenged, and the result, while not always groundbreaking, was always interesting and smart. His dirty little secret was he was a much more intelligent guy than he let on, and a much better listener than most people in television. But he really believed that his guest was the star, and his job was to help reveal that.”

One of King’s more memorable interviews took place at the end of 1999, when the Artist Formerly Known as Prince appeared on Larry King Live following the release of his first conventional album in three years, Rave Un2 the Joy Fantastic. While the “1999” tie-in made Prince an easy choice as a subject in December ’99, there was plenty of more timely subject matter to cover for the Artist than cute, chronological connections to the titular hit from his 1982 album. Over the course of the 35-minute interview, King cajoled the famously esoteric pop star into earnest considerations of his many against-the-grain decisions in the music industry and his personal life.

King’s earnest questions and the Artist Formerly Known as Prince’s constant self-reflection, complex self-image, and soft-spoken repudiations gave the interview an unusual cadence. While Prince demurred many of King’s broad, “of the people” question premises, even the questions he declined to directly answer wound up providing unique insights into his complex persona.

Early in the conversation, for example, King attempted to push Prince down one road (King: “You consider yourself an unusual personality…”; Prince, chuckling: “Depends…”) only to find himself in the middle of an even heavier topic, the thought process behind a global superstar changing their name mid-career, citing Cassius Clay (Muhammad Ali) as the only other example that came to mind.

“That was one of the things that I dealt with,” Prince noted about the prospect of a famous person dropping the name that made them famous. “I really searched deep within to find out the answer to whether fame was most important to me or my spiritual well-being, and I chose the latter.”

Prying on the notion of the “Artist Formerly Known as Prince” moniker as a media creation, King inquired, “How do you promote a symbol?” As Prince replied, “What we’ve found is, throughout the world, if you hold this [the symbol] and ask what they think of, they will say ‘Prince.'”

While Prince once again brushed off King’s follow-up premise (King: “Could you tell us what it signifies?; Prince, chuckling: “Well, me”), Larry adjusted, goading him into an explanation of the origins of the symbol that had at that point replaced his name and the advantages and pitfalls of this highly unusual but attention-grabbing decision.

This exchange, all of which took place before the program’s first commercial break, encapsulates what made King such a successful interviewer. He would go for the big topics but not apply too much pressure, instead remaining nimble to meet his subject where they were and converse on their level. In this short segment, using genuine interest and candor, King guided the rejections of the initial premises by his subject into genuine reflection on the topic he had been attempting to approach to begin with.

The full 1999 Larry King interview with Prince moved forward in the same fashion. The interviewer continued to goad his subject into honest reflection on a range of topics, from his word-of-mouth rise to prominence in Minnesota to reconciling his sex-forward image with his religious faith to his long, fraught battles over publishing copyrights to why he started writing “slave” on his face to the inherent entropy of our world to his own classification of his music (“The only thing I could think of is ‘inspirational'”). All the while, viewers were treated to a rare look inside one of the most nuanced yet guarded minds in music history.

Then, at the tail end, a surprise came in the form of a guests appearance by bassist Larry Graham (Sly & The Family Stone), who spoke about joining up with Prince to go on tour, adding an insider’s perspective to this rounded snapshot of the Artist at a notable point in his history.

Revisit the full 1999 Larry King interview with the late Prince Rogers Nelson below:

Larry King Interviews Prince Rogers Nelson – December 10th, 1999

[Video: CNN]