Top 10 Iconic 2000s Interview Moments

“Late Night with Conan O’Brien” (1993-2009)

Years before Jay Leno and Conan O’Brien’s late-night feud, Howard Stern showed up on the latter’s program to dish out some knowledge. The “King of All Media” arrives seemingly from the future to deliver the “Late Night” host a dire warning. Stern doesn’t mince words about Leno, saying that the “Tonight Show” presenter won’t leave his job quietly. It’s quite an insightful comment considering the 2010 scandal. Whether you like him or not, the radio personality predicts some of the ensuing conflicts with both humor and honesty. It wasn’t the first or last time that he’d air out his opinions about the subject either. The interview might have seemed normal in 2006, but it later became an unexpected look at the future of talk shows.

“Primetime Glick” (2001-03)

From the mind of Martin Short, Jiminy Glick exists to mock the worst aspects of celebrity interviewers. The character welcomes comedy icon Mel Brooks for this “Primetime Glick” segment. Rather than suck up to the comedian, Glick gets personal with hilarious and condescending questions. Short’s performance underneath the suit couldn’t be funnier in one of his greatest roles. Even the filmmaker gets to crack a joke that almost breaks the host. With a straight face, the performer asks Brooks outrageous things about controversial topics. Both men come together with tremendous improvisation skills, elevating the press junket concept into an art form.

“The Ellen DeGeneres Show” (2003-22)

During her tenure as a talk show host, Ellen DeGeneres had trouble getting an interview from George Clooney. His nearby offices became the target of a series of pranks to lure him to the studio. After several attempts, DeGeneres finally pulled out all of the stops. She enlisted two legendary Cincinnati Reds players to entice Clooney out of hiding. At the very least, her dedication to the bit has to be admired. The result was an amusing adventure and a fun showcase of the guest’s sense of humor. With all of his charms, the actor makes the wait well worth it. The star shares memories of his childhood and keeps the segment light with his likable demeanor.

“The Late Late Show with Craig Ferguson” (2005-14)

Despite having one of the silliest talk shows around, Craig Ferguson still invited Archbishop Desmond Tutu for an interview. The result was one of the host’s finest moments. Tutu referred to the comedian as “crazy,” but in a positive way that opened the door for their incredible discussion. The two injected humor into a serious discussion about activism, injustice, and the state of the world. Ferguson’s incisive questions prompted the guest to unleash his wisdom about forgiveness. It’s no wonder that the presenter won a Peabody for this segment, highlighting his ability to draw laughs and deep thoughts. This underrated program elevated itself to legendary status with this unlikely appearance.

“Late Show with David Letterman” (1993-2015)

With her famous friends and reality shows, Paris Hilton was seemingly everywhere in the 2000s. This also included a stint in jail that overshadowed this David Letterman interview. While the celebrity wanted to talk about her other ventures, the comedian turned the appearance into an embarrassing interrogation. Hilton was an easy target for jokes given her high-profile status and wealth. She later stated her discomfort with the segment, but it’s clear she wanted to escape the topic right away. We’re not surprised considering the host’s fixation on her legal troubles. Whether you laughed or were left feeling awkward, this interview perfectly captured the hotel heiress’s hold on the media.

“Today” (1952-)

On his press tour for “War of the Worlds,” Tom Cruise was more vocal than ever about his love life and personal beliefs. This included his views on everything from Scientology to his thoughts about Brooke Shields’ handling of her postpartum depression. The actor got aggressive with “Today” host Matt Lauer about psychiatry and prescription drugs, sharing his strong stances with viewers. It’s completely strange to see a movie star arguing about Ritalin on a morning show. The segment might be one of the more uncomfortable moments in Cruise’s career, showing him in a more hostile light. It certainly didn’t help his reputation during one of his most controversial years of his fame.

“Primetime” (1989-2012)

During the early 2000s, Britney Spears was one of the most famous singers in the world. This also made her fodder for tabloid coverage regarding her relationship with Justin Timberlake. Diane Sawyer questions the pop star about her personal life and cultural influence, painting the vocalist in a negative light. The performer does her best to push back against questions regarding her status as a role model. You could easily point to this as one of many times the media was unfair to her. In hindsight, the segment looks even worse given everything that Spears went through. It’s both infamous and iconic in its own way as it charts one of the peaks of the singer’s career.

“Late Show with David Letterman” (1993-2015)

Sporting long hair and sunglasses, Joaquin Phoenix shocked audiences with this appearance on the “Late Show with David Letterman.” He also appeared to be somewhat aloof during the experience. With the host both amused and confused, Phoenix said he was going to be stepping away from acting. The entire segment was surreal when it first went viral in 2009. When the actor later explained it was all made up for a film, the whole thing morphed into a bizarre piece of sketch comedy. The actor managed to fool everyone in an entertaining and strange chapter of 2000s pop culture.

“Primetime” (1989-2012)

Whitney Houston sat down with Diane Sawyer to talk about her career, but it was far from a puff piece. The interviewer delved into Houston’s life, health, and personal demons. With the singer on the defensive, Sawyer pressed the star about her weight. It’s clear throughout that Houston was taken aback by the intense questioning. When the conversation turns to drugs, the vocalist famously says one quote that helped to immortalize the segment. This appearance highlighted the many personal demons that likely followed her until her untimely death. While the interview could be considered intrusive, it also reiterated that even the most successful people suffer behind the scenes.

“The Oprah Winfrey Show” (1986-2011)

Few talk show appearances have taken on a life of their own quite like this one. Tom Cruise appeared on “The Oprah Winfrey Show” with more energy than ever, showing excitement about his love life. The actor was hyperactive in an interview that included jumping on the couch. This particular move came to epitomize Cruise’s over-exposure in the media, with his relationship and behavior taking center stage. Some thought it was a bizarre display of emotion while others just turned the moment into a meme. It arguably became Winfrey’s most decade-defining interview, with even her Whitney Houston and James Frey talks taking a backseat to this segment.