9 Unforgettable TV Interviews

Public curiosity burns for shallow celebrity gossip, but television's most prolific interviewers know how to delve deeper. The right host can contextualize larger-than-life figures—from politicians to pop culture icons to fugitives from the American justice system—as multi-dimensional human beings, or, as is the case with some of the interviews below, can serve as a proxy for the audience's confusion at wild celebrity antics. Diane Sawyer's two-hour interview with Bruce Jenner airs Friday, April 24 at 9 p.m. EST on ABC. Here's a look back at nine of the TV interviews that have generated the most hype and have led to some of the most memorable moments. Will "Bruce Jenner: The Interview" make it 10?

David Frost Interviews Richard Nixon

David Frost's 1977 series of interviews with disgraced former president Richard Nixon is perhaps the highest-profile interview series ever produced for television. Since Frost had to pay to interview Nixon, there were concerns that his journalistic integrity had been compromised and the interviews would be meaningless, but Frost didn't hold back when he sat down with the former head of state.

Frost grilled Nixon on Watergate and the dubious legality of his activities in the White House with questions including his now famous interview opener, "Why didn't you burn the tapes?" In 2006, playwright and screenwriter Peter Morgan adapted the story behind the interviews into a stage play titled Frost/Nixon and into a film of the same name two years later. The success of both adaptations demonstrates the endurance of the legacy of Frost's Nixon interviews.

Jon Stewart Interviews Barack Obama

Throughout his Daily Show career, Jon Stewart has been no stranger to powerful world leaders, but his 2010 interview with President Barack Obama was the first time he got the chance to interview a sitting president of the United States.

Stewart, though admittedly liberal, has made a name for himself by both mocking and providing thoughtful commentary on figures from any political party. In this midterm-election interview, Stewart mixed in some comedy, but he didn't throw the president any softballs. He asked President Obama difficult questions about his expectations coming into office and his effectiveness as a leader and a change maker.

One particular moment that had people talking the next day was when Stewart referred to the most powerful man in the world as "dude." Clearly that slipup didn't upset the president too much, since he returned to the show in 2012 for what Press Secretary Jay Carney recently called one of the president's toughest interviews that year.

James Lipton Interviews Dave Chappelle

Inside the Actors Studio wasn't Dave Chappelle's first appearance after he walked off the set of Chappelle's Show and absconded to Africa to escape the stress of fame, but the extended interview with James Lipton in 2006 provided a great deal of insight that Chappelle's fans had been lacking. There are moments of poignancy and hilarity peppered throughout the interview, and the discussion places the outstanding sketch comedy of Chappelle's Show within the context of a complete, complex human being.

"Once you get famous, you can't get unfamous," Chappelle told Lipton and an audience of Pace University students. "You can get infamous, but you can't get unfamous."

Katie Couric Interviews Sarah Palin

Asking someone to name a few newspapers she has read doesn't seem like hardball, gotcha-journalism. When Katie Couric interviewed Sarah Palin, not only did Palin refuse to name a newspaper, she also seemed to interpret the question as an attack on her home state of Alaska.

Palin, who doesn't have a sterling interview reputation overall, was especially out of sorts during this entire CBS Evening News series, and the results were certainly not helpful to the McCain-Palin campaign. Couric, on the other hand, won both the Alfred I. duPont—Columbia University Award and the Walter Cronkite Award for Journalism Excellence for the series.

Barbara Walters Interviews Monica Lewinsky

Barbara Walters's interview with Monica Lewinsky in 1999 drew a record audience for a news interview. About 74 million people tuned in to ABC to watch Walters ask Lewinsky about her affair with President Bill Clinton. Lewinsky spoke candidly about the relationship, apologizing to Hilary and Chelsea Clinton, and to the nation as a whole. Since the end of his presidency, Bill Clinton has fairly successfully reinvented his image, but Lewinsky has had a much more difficult road to recovery. The Barbara Walters interview was one of the first opportunities she got to tell her side of the story in depth.

David Letterman Interviews Joaquin Phoenix

Even at the best of times, Joaquin Phoenix is a perplexing figure, and David Letterman certainly did not get him at the best of times. During the ramp-up to the 2010 release of the mockumentary I'm Still Here, Phoenix turned his public life into a performance. Phoenix feigned a mental breakdown, a retirement from acting, and the start of a career in hip hop music as part of the movie's marketing strategy. Despite some outrageous behavior, none of these things seemed entirely outside the realm of possibility, given Hollywood's track record of producing broken individuals.

Phoenix appeared on the Late Show as an unresponsive, haggard mess, and Letterman was left to salvage whatever he could from the uncooperative interviewee. There's some debate as to whether the encounter was scripted, but both parties deny that it was; either way, it's delightfully awkward to sit through.

Brian Williams Interviews Edward Snowden

Though it's now been largely overshadowed by the controversy caused by Brian Williams's fabrication of personal involvement in news events, there was quite a bit of hype surrounding his 2014 interview with NSA leaker Edward Snowden. This special was Snowden's first American interview after he had left the country and sought asylum in Russia.

Snowden is a polarizing figure, viewed alternately as a heroic whistle-blower and a traitor to the United States. This comprehensive interview gave people in both camps something to talk about.

Oprah Interviews Michael Jackson

When Oprah Winfrey interviewed Michael Jackson in 1993, people took notice. The record-breaking interview attracted an audience of about 90 million viewers, even before the infamous child molestation accusations forever changed the face of Jackson's career and public image.

Highly reclusive for 14 years prior to his talk with Oprah, Jackson revealed previously undisclosed information on topics ranging from his unhappy childhood to vitiligo, the disease he claimed was lightening his skin.

Jay Leno Interviews Hugh Grant

"What the hell were you thinking?"

This was question number one from Jay Leno to Hugh Grant in 1995. The Tonight Show was the first public interview Grant did following his arrest for public indecent conduct with prostitute Divine Brown.

That opening question from Leno set a new bar for future late-night TV interviews, and Grant's answer to it, though not enough to excuse his behavior, was a refreshing admission of error. He dismissed excuses that others had offered for him, offered none of his own, and stated flat out that he "did a bad thing."