Who Were the Most Fascinating People of 2006, According to Barbara Walters?

People are fascinating, although I think most of us would say we're not especially interesting. We don't have to be unless our jobs demand it, most of the time. But we're also nosey, and we want to know more about those who are that much more intriguing than the average human. For 22 years, Barbara Walters, one of the most prominent journalists and interviewers in American TV history, hosted an annual celebration of those she deemed to be the most fascinating people. From 1993 to 2015, she chose, typically, 10 people from across entertainment, politics, business, and elsewhere, and she interviewed each of them for an ABC News special.

Walters, who interviewed heads of states and reality stars alike with the same personality-focused approach, was someone who could get access to seemingly anyone. In November 1977, she landed the first joint interview with Egyptian president Anwar Al Sadat and Israeli prime minister Menachem Begin, while they were working out the terms of the eventual Egypt–Israel peace treaty. She landed the first-ever interview with Monica Lewinsky after the Clinton affair. But her process was also divisive. She was gung-ho pro-America when talking to world leaders. With celebrities, she often couldn't hide her disdain. She tried to force Ricky Martin out of the closet when she interviewed him for her 2000 special, something she later regretted. Her combative approach could get good answers out of reticent interviewees, but sometimes she was just awful to her subjects, like when she asked Celine Dion if she was anorexic.

The Fascinating People specials were an odd mixture of softballs and needlessly intrusive interrogation, leading to a mish-mash interview experience that is certainly intriguing if not necessarily revealing. The hook was seeing these big famous people agree to talk to Barbara, a rite of passage for any rising star. But how good were her picks for the most fascinating people of any given year? Let’s dive into 2006 to see the people we were apparently all talking about 20 years ago. I’ll also be a bitch and declare whether or not they were truly interesting enough to earn the label of “the most fascinating.”

Watch the 2006 episode here!

Andre Agassi 

2006 was the year that Andre Agassi retired from professional tennis. By that point in time, he had won 60 career titles, had completed the Golden Slam, and had been number one in the world on several occasions. He was a char

itable guy. He was one half of a sporting power couple alongside Steffi Graf. And he'd gone from having one of the best heads of hair in the business to a hot bald legend. Oh, and for a while, he had dated Barbra Streisand. Icon.

We all love a sports success story, and Agassi remains one of the most important Americans in tennis history. He had an incredible comeback story, going from number 141 in the world rankings to the top spot. He was a major celebrity too, and he got to end his career on something of a high, which isn’t all that common in a field where injuries and crash-outs see people forced into retirement by 30. And he’s a charming interview. I get this pick.

I wonder if Walters regretted not waiting a couple of years for when Agassi released his tell-all memoir, Open, in 2009. In it, he talks about his emotionally abusive father-slash-coach, being a garbage husband to Brooke Shields, and using crystal meth in the late-90s. That would have made for a very fun, bitchy interview. But this one is also fine!

FASCINATING? Yes. He’s no Andy Murray, of course.

Sacha Baron Cohen 

Remember when Borat took over the world? Remember when it got Oscar nominations? Sacha Baron Cohen’s all-consuming “satire” of America was seen as radical in its raunch. Not to be that person, but I never liked his work, and that was before his garbage politics were well known. I see the work behind it, and clearly the Borat character was effective in making Cohen’s rather rotten case, but the ways that being racist towards Kazakhstan was totally okay because ooh it’s satire always bothered me.

But it was 2006. George W. Bush was still in power. Shtick like this still worked, and most people outside of the UK didn’t know much about Cohen as a person. So I get the pick, and it does speak to the mystique around Cohen at this time that he does not sit down for an interview with Walters. I don’t think Cohen himself is as fascinating as the ideas behind his work, and all his attempts to be a “serious” actor make me laugh (shout out to the handful of us who watched Disclaimer despite it being aggravatingly pretentious.) As time has passed, I don’t think any of this has aged well. Comedy isn’t supposed to, in fairness. It’s the artform that dates itself the quickest. But jeez, if I never again have to hear a “my wiiiife” joke, I’ll be thankful.

FASCINATING? A bit.

Patrick Dempsey

Is this a safe space to admit that I have never watched more than a couple of episodes of Grey’s Anatomy? I know people who are devoted to that show and I have just never been able to get on board (frankly, Shondaland in general, outside of Bridgerton, leaves me cold.) There is a reason it’s still on the air and Ellen Pompeo is cashing those cheques. It made stars of its core cast, but Patrick Dempsey was not an unknown when he signed on. He was an '80s teen heartthrob turned jobbing actor who was in everything from rom-coms like Sweet Home Alabama to a miniseries where he played JFK.

As Dr. Derek "McDreamy" Shepherd, however, he was probably the hottest man on TV at that time, or at least the hottest who was specifically positioned by the show as a sex object. His relationship with Meredith Grey was one of the show's few constants for a long time before he was killed off in 2015. Network still ruled the roost of the TV world and it was some solid corporate synergy for Barbara’s ABC special to include one of the channel’s buzziest figures. The following year, she’d include Katherine Heigl on the list.

Don't cry for Dreamy, though. He's done great since then: starring in Michael Mann movies, headlining at least four different shows, and being crowned People's Sexiest Man Alive! He seems much happier not being on Grey’s.

FASCINATING? Eh, not really, but the branding makes sense.

Joel Osteen 

And now for the Yikes portion of the episode. Did you ever look at religion and think its biggest problem was that it wasn't a big enough scam? Step forward Joel Osteen, televangelist supreme and king of the prosperity gospel. That's the notion that God spreads his love through economic blessings. The 2000s were a big time for Osteen and his ilk, who the Bush administration had latched onto hard to kickstart a new culture war and ensure eight years of Patriot Act-enforcing, anti-abortion, anti-queer rights Republican rule. 2006 saw him sign a book deal that The New York Times reported was worth around $10 million, which is a staggering advance for a non-fiction title not written by a former President or Pope.

Osteen seemed like the perfect face of Bush era bastardised Christianity: money-driven, always shilling a product, very personality-forward, and not-so-subtly bigoted as all hell. But he was also charming enough to hook the likes of Oprah and Barbara. He didn’t seem quite as fire and brimstone as some of his contemporaries, and he wasn’t a bitter-looking old guy claiming that the earthquake in Haiti was the work of the devil, like Pat Robertson. If you want to mainstream this kind of evangelism, as was the case in the Bush era (and is very much in play in 2026 under Trump’s second term), then you get a guy like Osteen. And let’s be honest: “God wants you to be rich” is a very enticing message. I bet Barbara was intrigued by that.

Nowadays, Osteen is still a big deal in evangelical circles. He’s a big Netanyahu fan but he was also willing to break away from the herd to support George Floyd and his family. He’s also, of course, very rich. I mostly think of him through other people’s parodies of evangelical preachers, like Daveed Diggs’ character on The Boys.

FASCINATING? Yes, but probably not for the reasons Walters chose him.

Steve Irwin and Terri Irwin

On 4th September 2006, Steve Irwin died while filming a documentary on the Great Barrier Reef, after the barb of a stingray pierced his heart. He was 44. The memorial service for his passing was watched by over 300 million people worldwide.

The legendary Australian zoologist and TV host known to the world as the Crocodile Hunter was kind of iconic. I have incredibly clear memories of watching his shows before school, and of the day he died and my religious studies class spent an hour in pure shock. His legacy remains mighty, both in terms of animal conservation and as one of the most beloved figures in Australian pop culture. There was even a campaign to get his face on the money instead of King Charles III after Queen Elizabeth's death. His widow Terri and kids Bindi and Robert are still prominent figures continuing his work, running Australia Zoo and headlining conservation efforts worldwide. Steve was a big-hearted, larger-than-life guy who seemed to love what he did (even if it attracted some controversy over his methods), and his passing left a real hole in the world that his family helped to fill. His death was still pretty raw by the time of this special, making this the real emotional peak of the show.

FASCINATING? Of course! Also, remember when there were rumours that Terri was dating Russell Crowe?

Jay-Z

Look, we all know that Jay-Z is never going to be as interesting as his wife, even if his rags-to-riches story is undoubtedly fascinating. But it's 2006, and Beyoncé hasn't become BEYONCE yet. She's still willingly doing interviews in this period! And Jay's just released his "comeback" album, Kingdom Come, which was a major seller. 2006 was also the year he took over the Rocawear clothing brand (he sold the rights the following year for $204 million.) Time listed him and Beyoncé as the most powerful couple in their 100 most influential people issue. This felt like the beginning of Jay-Z becoming a full-on businessman, and, frankly, a mainstream figure that white media could no longer claim was scary or a threat to society.

The coverage of Jay’s early rap days was, as with the glut of “concerned” coverage of the genre in the ‘90s, a lot of scaremongering and racism. By 2006, rap was a multi-billion-dollar industry, and a chart-topping sound well beyond niche. Jay wasn’t the only figure leading that but he was certainly one of the savviest. You could make the case that 2006 was the year he fully began his evolution into CEO Mode, for better or worse (for worse, really, because some of his dealings are just outright awful.)

Walters doesn't really seem to know much about Jay or care about his work. I doubt she was listening to The Black Album before recording. At one point, she asked if Beyoncé was bootylicious. I hope to never hear that clip again for as long as I live.

FASCINATING? Yes, but Walters doesn’t seem to really know why.

Nancy Pelosi

Being the Democratic Speaker of the House in the middle of Bush’s second term made Nancy Pelosi a fascinating figure. In the 2006 midterm elections, Pelosi led the Democrats to a majority in the House for the first time in 12 years, becoming the first woman to ever hold that position. She was a major fundraising force and perhaps the most prominent woman in US politics at that time next to Condoleezza Rice. And she was the GOP's boogeyman. The midterms of 2006 were dominated by ads that treated Pelosi like she was going to steal your Social Security and make your kids gay. Frankly, it made her seem way more progressive than she was. Just look at the current state of the Democratic Party for proof of Pelosi’s legacy.

Pelosi was the only politician on the list this year. Condoleezza Rice was on the previous year's special, and Bill Clinton would be there for 2007. Walters never seemed to favour one party over the other, and her choices for what would be fascinating for each candidate are erratic. Sarah Palin made sense as fascinating for 2008, but why was she on the list again in 2009 AND 2010?! You get the feeling that Walters was easily swayed by buzz or whatever ABC wanted her to do. It's not like any of her interviews with these politicians were especially hard-hitting, at least not in this format. That or some people were just easier to book than others. She had Donald Trump on so many of these specials, guys.

FASCINATING? Yes.

Brad Pitt and Angelina Jolie

Well, we all know what happened with this pair in 2006, right?

The previous year, Mr. & Mrs. Smith had been released, and Brad Pitt and Jennifer Aniston announced their divorce. Everyone took sides in the great Brangelina scandal, with the lion's share of the press deeming Jolie to be a husband-stealing manipulator. You remember the headlines. At the beginning of 2006, Angelina confirmed she was pregnant with Shiloh, and she gave birth in May. The first images of the baby were sold for a record high price.

It’s tough to talk about Brad and Angelina given what we know now. It cannot help but make you worry about what we don’t know, about what Jolie and her kids experienced behind closed doors during the pair’s relationship. Pitt is still trying to hurt Jolie, and to keep the press in his corner even as all his children go out of their way to legally drop Pitt from their names. But at the time, in 2006, everyone was OBSESSED with this pair, and they knew how to play the game.

Jolie made Pitt more interesting. He went from a perfectly nice himbo to an enigmatic figure when he met Angelina. The chemistry was undeniable but she was also the one-time bad girl turned humanitarian who went out of her way to walk the walk with her philanthropy. She’s still doing that, forever consistent and staunch in her beliefs. You can’t fake sheer magnetism. Angelina has it in spades, and Brad, who was always one of those guys who took on whatever image or aura his girlfriend at the time had, embraced her brand of purposeful mystique. The power couple force was off the charts, but it was largely her doing. Yes, I’m biased, but come on, you know Brad can’t do it alone. That’s why he needs publicists and lawyers and a new angle as a dog dad to clean up his mess (hey, dogs can’t file FBI reports.)

Always and forever, fuck Brad Pitt. If Brad Pitt has no haters, I am dead. But yes, in 2006, no power couple was more fascinating than Brad and Angelina. They didn’t sit down for a joint interview with Barbara, although we do get a brief clip of an interview Jolie did with Walters from years before. Indeed, they wouldn’t do that for many years. It speaks to how major they were that Walters included them in the special without securing a sit-down. The segment is also pretty positive about the pair's love story, never positioning Jolie as The Other Woman but instead having their union be almost an act of fate. Brad and Angelina were a big enough deal that they could bypass the rules, and the formation of Brangelina was even mightier.

FASCINATING? Yes, 100%.

John Ramsey

By 2006, it had been a decade since the murder of JonBenét Ramsey, and America hadn't grown any less obsessed with the horrifying case. It was a melting pot of true crime ghoulishness: the child beauty pageant winner and all those images of her in make-up and frills, the brutality of her death, the oddness surrounding the supposed ransom note, and the lack of closure around the whole thing. JonBenét's parents, John and Patsy Ramsey, had been indicted by a grand jury for child abuse resulting in her death. Then-district attorney Alex Hunter declined to sign the indictment, saying there was insufficient evidence. Patsy died in 2006, with the cloud of suspicion still around her.

So, why was John chosen for this otherwise pretty fluffy programme? Well, Walters had interviewed the Ramseys before. That year, John Mark Karr, a 41-year-old school teacher, was arrested in Bangkok and made a false confession of having killed JonBenét. When asked about that, John Ramsey admitted that he "started feeling sorry for the guy" who clearly didn't do it. He also talked about missing his wife, hoping to see her and their daughter in heaven, but still having things to do in this life before that. From what I can ascertain, this interview just made the armchair detectives who believed the Ramseys killed their daughter more convinced that he did it. They didn't believe he was sad or penitent enough in his answers. He dared to smile at a couple of points. Have I mentioned before that I really hate how the true crime industrial complex has ruined all of our minds?

FASCINATING? Dude, how do I even answer that about the father of a child murder victim? Barbara, you could be weird.

Anna Wintour

In 2006, The Devil Wears Prada was released. The film was a huge hit and drew further attention to the source material, a novel by Lauren Weisberger, a one-time assistant to Vogue editor-in-chief Anna Wintour. In the film, Miranda Priestly, the thinly veiled Wintour stand-in, is aloof and with a withering glare who doesn’t have to raise her voice to strike fear into her staff. Weisberger’s version is more traditionally gorgon-esque. But both made it impossible for Wintour to avoid the stories people had been spreading about her for decades. Of course Walters would have wanted to know if she was really that bad.

It took Wintour a good few years to embrace The Devil Wears Prada. With this year’s sequel, Vogue went all out in helping to promote it but they acted as though the first movie didn’t exist for the longest time. One wonders if the press-shy Wintour decided to talk to Walters because she was keen to diffuse the rumours of her tyrant reputation. She is very complimentary of the film and Streep’s performance in it during their sit-down but is also keen to stress that it’s fiction. Nobody believed her, shockingly.

I also wonder if she was hesitant to do press like this lest it impact the mystique of Nuclear Wintour, bob and all. The documentary The September Issue saw her be similarly cagey, but in her natural habitat. Nowadays, Wintour has savvily embraced the jokes about her brand while maintaining an iron grip over it (sorry, Chloe Malle, but we all know who really runs the show.) But in 2006, she was still a closed book.

FASCINATING? Yeah, I’ll give Barbara this one.

WHO WAS MISSING?

2006 was the year we got Daniel Craig’s first role as James Bond. Martin Scorsese would finally win Best Director the following year for The Departed. High School Musical became a mega-hit and one of the year’s best-selling albums. Taylor Swift released her debut. The console wars entered a new generation with the Xbox 360, the Wii and PlayStation 3. Twitter was launched, but it would take until at least 2008 for it to be noticed. Saddam Hussein was executed. Wikileaks was founded. Pluto was downgraded to a dwarf planet.

Shows like this are meant to be reasonably fluffy, albeit with the illusion of heft. Like a VH1 list show or edition of the VMAs, they're meant to be a weird little time capsule of the moment as it's happening. Fads often overshadow moments that had a bigger long-term impact. That sure-fire success may not have seemed so obvious in the moment. And the monoculture meant that there was a greater effort to have shows like this appeal to as many people as possible. If this show happened now, it would almost entirely be clips of the featured people without a sit-down interview, unless they were more niche. Like, you wouldn't get Jay-Z now, but I'm sure some podcast bro would do it. Not that those losers need more attention.

Who do you think would be on the 2026 list? Curry Barker? Ella Langley? Abdul Al-Sayed? Someone from the Spanish football team, maybe? Probably Taylor Swift, let's be honest.