Renaissance man James Lipton, who died Monday at age 93, wore many hats as an actor, theater, film and television director and producer, choreographer, author, playwright, lyricist, screenwriter, author, academic and even a pimp.

But it was his remarkably in-depth interviews on Bravo’s “Inside the Actors Studio” that cemented him as a Hollywood icon. The talk show, which doubled as part of the master’s degree program at the Actors Studio Drama School at Pace University, saw several water-cooler moments throughout its 24 years, thanks to the host’s signature and oftentimes shocking insight into his guests’ craft and lives.

From the question that stumped Steven Spielberg to his tearful reunion with Bradley Cooper, here are some of Lipton’s greatest hits.

Steven Spielberg (1999)

While discussing his 1977 sci-fi epic “Close Encounters of the Third Kind,” Lipton stunned Spielberg with a thoughtful inquiry about the filmmaker’s parents. In the film, aliens and humans communicate via a sequence of musical tones, generated by a computer.


“Your father was a computer scientist; your mother was a musician,” Lipton ventured. “When the spaceship lands, how do they communicate?”

“That’s a very good question; I like that,” Spielberg said with a grin, before replying, “I’d love to say I intended that, and I realized that was my mother and father, but not until this moment. ... Thank you for that.”



Julianne Moore (2002)

One of Lipton’s most educational interviews was with Moore, who was happy to impart the most influential lessons she had learned from her various teachers and sweeping body of work.



Dave Chappelle (2006)

Comedian Chappelle got serious while speaking with Lipton about his complicated road to fame and then-recent headline-making decision to walk away from a $50-million deal with Comedy Central.


“The higher up I went, the less happy I was,” Chappelle said during the conversation. “Once you get famous, you can’t get unfamous. You can get infamous, but you can’t get unfamous.”



James Lipton (2008)

In celebration of the program’s 200th episode, Lipton put himself in the hot seat, inviting Chappelle back as his interviewer. Among other revelations, Lipton disclosed his favorite expletive — “Jesus Christ” — and that he once worked as a pimp in 1950s Paris.



Jack Lemmon (1998)

During a sit-down with Lemmon, Lipton referenced a scene from “Days of Wine and Roses,” in which Lemmon’s character, Clay, reveals he is an alcoholic. Another unexpected reveal followed when Lemmon interjected, “Which I am, incidentally.”

When Lipton asked the actor to clarify whether he was “talking as Clay now or as Jack Lemmon,” he responded, “No, as Jack Lemmon. I’m an alcoholic.”


The interview marked the first time the movie star spoke publicly about his addiction.

Robin Williams (2001)

Over the course of five hours, Lipton conducted a lively interview with Williams, during which the comedy legend showcased his signature quick wit and opened up about his personal struggles.

The extended segment also merited one of Williams’ most enduring improv performances, prompted by Lipton, involving an audience member’s pink scarf.


“For those of us who have not been blessed with your gift, how do you explain the mental reflexes that you deploy?” Lipton asked, inspiring Williams to launch into his routine. “Are you thinking faster than the rest of us? What the hell is going on?”



Amy Poehler (2009)

Another great masterclass in comedy came from Lipton’s conversation with “Saturday Night Live” alum Poehler, during which the host challenged his guest to perform a number of hilarious impressions, from Christopher Walken to Paula Abdul.



Paul Newman (1994)

In 1994, Lipton kicked off “Inside the Actors Studio” with none other than screen icon Newman, who served as president of the studio from 1982 to 1994. Together, the pair went behind the scenes of a number of Newman’s projects, including “Butch Cassidy and the Sundance Kid,” “The Long Hot Summer” and “The Left-handed Gun.”



Bradley Cooper (2011)

Lipton often said he most looked forward to interviewing one of his own students who had achieved enough success to come full circle on his show. That student ended up being Cooper, who could barely keep it together for his edition of “Inside the Actors Studio.”


The “A Star Is Born” mastermind had appeared on the program in the past as a curious pupil posing questions from the audience to his acting heroes.