The best interviews are rarely, if ever, brief. With a tight window, the interviewer is never able to establish a rapport with their subject. They are never able to coax their guest into believing, if only for just a moment, that there conversation is private, amongst friends. There is no breadth, no backstory, and the topic of the day is lost in staged soundbites and niceties.
Of the interviewers who have earned a broadcasting format with the necessary time and structure to achieve great interviews, three standout to me for their excellence: Terry Gross, Howard Stern (if you have never listened to one of his interview, check out this one with film mogul Harvey Weinstein), and of course, Charlie Rose.
Charlie Rose's interviews span film, current events, and science to dive deep into the world around us with guests at the apex of their fields. Using an all black backdrop that elicits the desired seriousness and intimacy with guests, Charlie Rose has the gravitas to almost always deliver the right questions. With that said, these are my top 5 favorite Charlie Rose interviews:
Steven Pinker is a prolific psychologist and linguist whose research into the origins of the human language, the mind, and evolution have made him both revered, and in some small-minded circles, reviled. His book The Blank Slate—named for the theory, which he duly strikes down, that the human mind is blank at birth and programmed in its entirety by exogenous culture—is brilliant and I highly recommend it. In this interview, Professor Pinker discusses his book The Better Angels of Our Nature in which he argues that we are living in the most peaceful period of human existence. Pinker is a genius and he doesn't disappoint here.
As he begins this clip proclaiming, DiCaprio is loathe to give long form interviews because he believes it detracts from the audience's ability to detach the actor from the character. That he steps away from this reluctance is what makes this interview such a treat. I have seen virtually all of his films, but other than the tabloids about his understandable taste for supermodels, felt like I had never really heard him speak. You get a bit of it here and he is surprisingly eloquent.
David Foster Wallace
Several years after his suicide, Wallace is back in the news this summer with a new film depicting a few esoteric days in his life—I have yet to see it but the reviews have been quite good. This interview dates from 1997 and follows Wallace's ascent into the, relative, mainstream of literary culture with the success of Infinite Jest. In this interview, Wallace is visibly (and admittedly) uncomfortable, but also painfully himself, while he spouts his brilliant observations across literature, films, and life. Knowing how his life ends makes this interview all the more dramatic and tragic.
Christopher Hitchens was one of the fortunate few to speak his mind and maintain his mantel as a public intellectual. Even when taking positions I wholeheartedly disagreed with—like initially supporting the Iraq war—his wit, intellect, and charm prevented me from thinking worse of him. His later book God Is Not Great is, for lack of a better word, holy to the secular movement and a must read for anyone (religious or not) that is interested in religious history or dogmatic implications. I could have picked any of Hitchens interviews on Charlie Rose, he did many and was it seems a good friend of Rose's, but landed on this timecapsule from 2001.
Lee Kuan Yew
Sitting like a weigh station in the Strait of Malacca, Singapore has long been of strategic importance to global commerce despite being geographically baron of any vital resources. Following an acrimonious rift with Malaysia, Lee Kuan Yew almost singlehandedly turned the Singaporean island into a prosperous city state that rivals only the Venice of yore. Forgiving his benevolent autocratic tendencies, Lee Kuan Yew—who passed away in March of this year—was one of the most brilliant political thinkers of the 20th century. This interview, even in his old age, gives you a brief taste of his wisdom.
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