15 Awkward Interview Moments From The 2000s That Aged Like Fine Milk

Gaga’s early bops were full of sexually explicit references. This seemed to worry a reporter, who felt that people might take her less seriously because of her risqué lyrics.

“Are you scared that having sexual references can undermine your music?” he asked Gaga.

“I’m not scared, are you?” she replied.

The pop icon then said the biggest thrill of her career were her fans—more specifically, “the gay community”—because they didn’t ask her “stupid questions like that” and “love sexual, strong women who speak their mind.”

If she were a man, she told the interviewer, she’d be called a “rockstar” for singing about “fast cars and f***ing girls.”

“But when I do it in my music and in my videos, because I’m a female and make pop music, you’re judgemental.”

After all, she said, she is a rockstar, too.

In 2002, the then-16-year-old twin stars Mary-Kate and Ashley Olsen were interviewed by Connie Cheung, known for her rapid-fire sharp questions.

Unfortunately, one of them was related to the sisters’ virginity.

Speaking of Cheung’s question about whether they had already had intercourse, Ashley later told Rolling Stone she got “really angry and defensive.”

“That's personal. Why would you be asking a 16-year-old that question in the first place?”

Shortly after the uncomfortable interview, the teenagers were photographed in their bikinis during a trip to Hawaii. The intrusive paparazzi photos, which Ashley referred to as her “worst nightmare,” had her “crying hysterically.”

Anderson Cooper is arguably one of the most respected journalists on American television. Still, even the CNN star isn’t exempt from making a faux pas in his career.

During a 2009 interview on 60 Minutes Overtime, he asked Lady Gaga to clarify a very bizarre rumor that was circulating online at the time—that the popstar had a penis.

“Why the hell am I going to waste my time and give a press release about whether or not I have a penis?” the Million Reasons singer responded. “My fans don’t care, and neither do I.”

In recent years, Ellen DeGeneres has faced social media backlash after several clips resurfaced showing the host asking tactless questions to her celeb guests.

The online criticism, mounted on top of allegations of a toxic work environment, ushered in the finalization of the daytime talk show after nearly 20 years on air.

This unearthed 2008 clip of Mariah Carey sheds light on why that happened.

After Mariah refused to disclose whether or not she was pregnant, Ellen dared her to drink alcohol to prove that she was. “Let’s just toast champagne and decide…” the host said.

Recalling the incident, the singer told Vulture in 2020: “I was extremely uncomfortable with that moment is all I can say. And I really have had a hard time grappling with the aftermath."
"I wasn't ready to tell anyone because I had had a miscarriage...I didn't enjoy that moment."

But Chung’s isn’t the only out-of-place question that the child stars had to tolerate. In 2004, Oprah asked them to address the rumors referring to their alleged eating disorder.

“I know a new rumor [that’s] recently surfaced has really upset you, right?” the famous TV host told the sisters. “You know, the one about eating.”

The Olsen Twins responded: “You know, people are going to write what they want. We try not to read the good or the bad.”

The host of The Oprah Winfrey Show then insisted on the topic, asking them, “What size are you, by the way?” as a follow-up question.

When the sisters admitted that they didn’t know their size, Oprah looked jokingly at the live studio audience.

The clip resurfaced two years ago, with many fans pointing out that the interview made the sisters feel uneasy.

In 2004, Posh and Becks’ relationship spiraled into chaos—the football icon was accused of having an affair with Rebecca Loos, his former personal assistant, a story he dismissed as “ludicrous.”

The following year, Emma Bunton (a.k.a Baby Spice) went to The Howard Stern Show and was pressured to address her former bandmate’s situation.

After speaking about the cheating scandal, the host proceeded to sexually threaten her about not answering the question.

“If you don’t talk about this, you’re gonna have to take your pants off, and that’s going to be embarrassing,” he said.

When the Spice Girl refused to obey, Howard persisted in a creepy tone. “Oh, yes you are. Your dad isn’t here to protect you.”

In an incredibly creepy moment on The Howard Stern Show from 2002, the host and his colleagues tried to take bets to guess how much Anna Nicole Smith weighed and forced the star to step on a scale live.

“I’m saying 300,” Stern guessed.

“I’m not gonna get on a scale, but you’re way off,” the model replied, to which the radio personality said, “I’ll show you my penis if you do.”

The interview continued as if nothing had happened, with the broadcasters insisting on knowing her weight.

“Anna, just get on the scale, it’s no big deal!” Howard’s co-workers yelled.

Britney’s brand-new memoir proves that her private life has long been subject to intense media scrutiny. For her and other pop stars, being in the spotlight in the early 2000s meant exposition to some really nosy journalists.

When the pop icon sat down with Diane Sawyer in 2003 for a heart-to-heart interview, Diane asked her about losing her virginity before marriage and what advice she’d give her 12-year-old sister, Jamie Lynn, about premarital sex.

Britney was born in the Bible Belt, where socially conservative evangelical Protestantism has a strong influence.

“If you can wait ‘till you're married, I think you should definitely do that. But, in reality, if you really know in your heart that you are going to be with that person forever, and you’re four or five years into the relationship…” Britney gracefully responded.

Referring to her younger sister, she said she could only “give her unconditional love and trust.”

If wardrobe malfunctions are incredibly embarrassing at any public event, imagine what it’d be like to have that incident captured on camera.

Imagine going on a red carpet event and being all glammed up, only to have your dress accidentally reveal your underwear for hundreds of paparazzi to photograph.

And then having David Letterman humiliate you for it on TV in front of millions of viewers.

Though she laughed off the cringe moment back in 2009, it’s safe to say that Emma Watson has more than a few reasons to not speak to the late-night host ever again.

Some celebrities make it extremely clear that they don’t wish to address a specific topic, whether it be a recent breakup, family loss, or, in Leighton Meester’s case, a troubled childhood.

“I lived in NYC for about three years as a preteen, which I don’t want to remember. The worst years,” the Gossip Girl actress shared during a 2009 interview on The Ellen Show.

Still, Ellen insisted on having Leighton speak about her childhood. “Tell people the situation that you were in,” the host said.

At this point, it was really evident that Leighton didn’t want to speak about her parents, as she vaguely said that they had been “part of an interesting lifestyle.”

At that point, Ellen directly asked her, “They were in prison, right?”, which the interviewee confirmed.

"One, that's none of my business or your business to even ask that question, and it's completely out of line."

That was Anne Heche’s answer to being asked if her then-husband, Coleman Laffoon, had ever had "a same-sex experience in his past that would have left him open to a broader worldview.”

When the Advocate interviewer offered an apology, Heche insisted that she should be the main focus of the interview.

“This is not an article about Coley...I'm finished with this conversation,” she said. 

“You have got to be kidding me, after everything I have given you, you are now asking me about my husband's sexuality? That is flooring to me."

When they attended the 2007 Virgin Festival, the lead singer and the guitarist of the Arctic Monkeys were asked who they wished was a virgin among their famous peers.

Both rockstars were left speechless and refused to give an answer.

Not sensing how awkward the interaction was becoming, the MUCH music reporter stood for a minute waiting for the stars to give out a name while Turner and Cook stared at each other, laughing uncomfortably.

Surprisingly, the interview carried on for three more minutes following the uncomfortable silence, with the American interviewer struggling to make out what the two Brits were saying.

In 2007, Paris Hilton was invited to the David Letterman show to promote her brand-new perfume, Can Can. Or so she thought.

“How’d you like being in jail?” the late-night host randomly asked.

“Umm… not so much,” answered the businesswoman.

The previous year, Hilton had her license suspended after being caught driving under the influence. A few months later, while on probation, she was pulled over for driving 70 mph in a 35-mph zone without headlights at night, and a judge sentenced her to 75 days in jail.

The magnate referred to the interview–and her feeling of being back-stabbed by Letterman—in a 2021 episode of her podcast, This Is Paris.

As she explained, the famous host had promised that he wouldn’t bring up the arrest but kept “pushing and pushing” her to address it once she got in front of the camera.

“I felt like it was a safe place because I'd been going on Letterman for so many years. He'd always have fun with me and joke around, but I thought he would keep his word on this and I was wrong,” she said.

Back in 2009, Justin Bieber’s hair flip and catchy pop tunes were all the rage. Girls wanted to be picked to go onstage for his special One Less Lonely Girl live performance, and One Time played at every radio station to the point of exhaustion.

That year, the Canadian star did an interview that showed he never cared about the doubters, not even when he was 15 years old.

“Critics will say that you are basically a product of marketing,” the CTV News interviewer, Sandie Rinaldo, told the then-teenager.

Bieber said in response that his success “happened organically” and that his record label didn’t “push” anything.
“Coming from Stratford, Ontario, it basically gave others hope, because nothing really comes from there.”
 
Rinaldo insisted that other famous people had come from the small town, such as Canadian news anchor Lloyd Robertson, a comeback that didn’t exactly sit well with the world-famous Sorry singer.

What would have been one of the most critical performances in Janet’s music career—performing at the Super Bowl halftime show—turned into a living nightmare after a wardrobe malfunction exposed her breast while performing with Justin Timberlake.

Three years after the incident, labeled “nipple gate” by the media, a journalist thought it’d be wise to bring up the traumatizing event during a press junket for Janet’s comedy-drama film, Why Did I Get Married?

“Hey Janet, anything happened to you at the Superbowl?” one reporter asked.

Another one inquired, “How often do you consider that you singlehandedly rocked the broadcast world?”

Fortunately, her co-star Tyler Perry intervened to shift the conversation towards their movie. “When it opens on the 12th here, I think people will see how great of an actress she is,” he said.

Plus, the actor ignored the accident by speaking about his love for his favorite football team: “I absolutely am hoping that the Jets go to the Super Bowl this year. I really am!”