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Remembering 5 of James Lipton's greatest moments from 'Inside the Actors Studio'

Bradley Cooper, Robin Williams and Sally Field were among the host's memorable guests.

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/ Source: TODAY
By Randee Dawn

Anyone can ask interview questions, but few really know how to listen, which made James Lipton and his show "Inside the Actors Studio" such great television for nearly 25 years.

Lipton died on Monday at his home at the age of 93, having retired from the show in 2018. He was almost as fascinating as the scores of actors he interviewed over the years.

So in honor of the great interviewer, who never shied away from a question and never failed to listen thoughtfully to an answer, we tracked down some of the greatest moments in "Inside the Actors Studio" history.

Bradley Cooper

Bradley Cooper appeared multiple times on "Inside the Actors Studio," including a few appearances while a student.NBC

You don't usually get a student in the audience who not only gets to ask a question ... but goes on to ultimately be a guest, but Cooper did exactly that. While studying at Pace University's Actors Studio Drama School in the 1990s, he popped up to ask questions of Robert De Niro and Sean Penn, and showed up in the front row when Steven Spielberg sat in the chair. Cooper got his own moment in the spotlight in 2011 and again in 2013, for the show's 250th episode.

What did we learn about him? "I'm a loud crier," he admitted. "It's ugly, so I apologized."

Amy Adams

Lipton with Amy Adams at a post-"American Hustle" premiere party in 2013 in New York City. Monica Schipper / Getty Images

Adams joined Lipton three weeks after Philip Seymour Hoffman's death in 2014, and she spoke emotionally about her admiration for the man she co-starred with in three separate films ("Charlie Wilson's War," "Doubt" and "The Master").

"He was beautiful," Adams said, according to IndieWire. "He had this unique ability to see people, to really see them — not look through them — he just really saw people. And he will be missed. Sorry, I really… I just really loved him and I know so many people did."

Robin Williams

James Lipton and Robin Williams at the opening night party for "Bengal Tiger at the Baghdad Zoo" on Broadway in New York City in 2011.Bruce Glikas / FilmMagic

The entire interview with the late comedian (who died in 2014) is five hours long and of course studded with hilarious moments and explorations of Williams' darker moments. During the 2001 interview, Lipton did his best to find out how Williams could riff the way he did: "Are you thinking faster than the rest of us?" the Observer reported him asking. "What the hell is going on?"

And the answer ended up being a seven-minute take on an audience member's scarf that had everyone in stitches.

Dave Chappelle

In 2006, Chappelle had a new project (the documentary "Dave Chappelle's Block Party") but everyone really wanted to know why he'd abandoned a $50 million Comedy Central contact, walking away from the third season of "Chappelle's Show" and hiding out in South Africa. Lipton knew when to hold back and let his guest go on, and eventually Chappelle did, noting he hated that people called him "crazy."

"The worst thing to call somebody is crazy," Chappelle said. "It's dismissive — 'I don't understand this person, so they’re crazy.' That’s bulls---. People are not crazy, they're strong people. Maybe their environment is a little sick."

For the 200th episode of the show in 2008, the tables turned: Chappelle was the interviewer and Lipton the guest, where he first revealed he worked as a pimp in his previous life. "I did a roaring business," Lipton said.

Sally Field

Revelations were not unheard of in the welcoming space of the show; in 1998 Jack Lemmon revealed he was an alcoholic, something his wife later told Lipton that he'd never shared with anyone other than her. But in 1994 the Oscar-winning Field startled the audience with her own frank admission.

"I personally don't know what the big deal is about taking your clothes off," Field told the audience, after being asked about nude scenes in films. "I wish somebody would ask me to take my clothes off."