TV

A Look Back at 10 of Larry King’s Most Memorable Interviews

From politicians to comedians, King could coax a revealing conversation out of anyone

Larry King in 2010

By Tobias Carroll

When revisiting the indelible broadcast legacy of the late Larry King, one thing quickly becomes apparent: King interviewed everybody. Not literally, but consider this: there are interviewers who specialize in politicians and world leaders, and interviewers who work well with artists and entertainers. Not too many seem equally at home talking with both groups. To his credit, King was — and any attempt to compile a list of his most memorable on-screen moments should reflect that.

Some of the best interviewers create a sense of comfort for their subject; others seem to vanish from the conversation entirely, making the person being interviewed snap into prominence. That wasn’t the case with King; in a 2015 profile, Mark Leibovich observed that “King let his guests talk until he became bored, which tended to happen quickly.” This could lead to unexpected shifts mid-conversation — but it also kept things fresh throughout. 

Over the course of his long and illustrious career, King conducted countless interviews — some of them revelatory, some of them candid and some of them flat-out weird. Here’s a look at 10 that strike us as especially noteworthy.

Nelson Mandela (2000)

King was best known for his work interviewing celebrities, but he also had a penchant for speaking warmly with global leaders. In this clip from a 2000 interview with Nelson Mandela, King walks Mandela through one of the most critical moments of his life, offering viewers an intimate view of history being made.

Jerry Seinfeld (2007)

What happens when an interviewer with an outsized personality meets a subject with an equally heightened persona? Larry King’s 2007 conversation with Jerry Seinfeld took a turn for the strange in the clip above, when Seinfeld took umbrage to the phrasing of one of King’s questions. It might have been awkward at the time, but it’s also more than a little entertaining.

Bill Clinton (1994)

When a sitting president does an extensive interview, it’s news in and of itself. This conversation between King and Bill Clinton from 1994 certainly serves that purpose. But it’s also a testament to how prominent King was in his prime — at around 22 minutes in, Clinton speaks of King’s program as a way to “break through to ordinary Americans.” Sometimes, the monoculture is best personified by a dapper man in suspenders.

Norm MacDonald (2016)

Pair a candid enough guest with King’s penchant for wide-ranging questions and you might end up with something genuinely memorable. This interview with Norm MacDonald, from around the time of the 2016 presidential election, finds King leading MacDonald through a variety of topics. MacDonald’s never been one to avoid oversharing; here, that candor turns into something approaching insight here.

Faye Resnick (1994)

King spent 25 years working for CNN, and as the network’s profile grew, so did his. The O.J. Simpson murder trial was a seismic moment for cable news in America, and it’s a moment in media history in which King played a significant part. King’s interview with Faye Resnick, a friend of Nicole Brown Simpson’s, was later adapted on the first season of American Crime Story, with Connie Britton playing Resnick. Playing the role of Larry King was … Larry King

Paul Newman (1998)

The many celebrity interviews King conducted over his career could reveal the innermost thoughts of ubiquitous screen presences. King’s 1998 conversation with Paul Newman finds Newman revealing a reticent side before revealing his secret for maintaining a long marriage while working in the film industry. (“Probably some combination of lust and respect and patience and determination.”)

Donald Trump (1987)

Larry King interviewed politicians and celebrities, and every once in a while he interviewed a celebrity who’d later become a politician. In this 1987 interview with Donald Trump, King quizzes him on some political matters. Trump’s answers eerily anticipate some of the same rhetoric he’d later use in his time in office. 

Eric Andre (2017)

Eric Andre’s own foray into the talk show format is the polar opposite of King’s: surreal and bizarre. Put the two men in conversation, however, and the result is absolutely brilliant. Andre fields King’s panoply of questions and topics with sincerity and enthusiasm, and King demonstrates his own talent for deadpan, absurdist comedy. Andre later described working with King as “One of my favorite interviews of my humble career and one of the sweetest guys i ever worked with.”

Frank Sinatra (1988)

Given the blunt discussion of mortality in this interview, it feels more than a little bittersweet now that both interviewer and interviewee are gone. But it’s also a great example of what happens when the two are in sync: King knows precisely the right tone to take with Sinatra, and Sinatra responds — both verbally and with some revealing facial expressions — in abundance.

Forest Whitaker (2013)

What’s notable about this 2013 interview with Forest Whitaker isn’t the interview itself — it’s what happens during it. King mentions to Whitaker that, early in his career, he’d covered Dr. Martin Luther King. Whitaker asks if he has any stories to share. King initially demurs, not wanting to shift the spotlight off Whitaker, but Whitaker insists. What follows is a moving tale from King’s early career — and a testament to just how well Larry King could tell a story.