Rare Photos From The 2000s No One Talks About
By | January 9, 2023
Leo, Johnny and Brad. Who’s your favorite?
The aughts were a decade where everything happened at once. A clash of styles occurred as civilization moved into the new millennium, while many people looked forward to a new era, others drew inspiration from the past.
These rarely seen snapshots from the 2000s show the enthusiasm and excitement that came with greeting a new decade, even if everyone was unsure of what exactly was going to happen. The excitement and sensuality of the decade spills over from each photo, so make sure you have plenty of time to spend on each shot.
If you’re ready to have your concept of the 2000s challenged then start scrolling through these fascinating photos from the first decade of the new millennium.
This article first appeared on our sister site: Historydaily.org
It’s weird to think about these three heart throbs hanging out, but when you’re young and famous in Hollywood there must be some kind of magnetic pull bringing you towards people who are just like you.
While Leonardo DiCaprio may be about 10 years younger than Depp and Pitt, he’s always had a sense that he’s an old soul - whether it’s in his film choices or the way he handles himself as a star.
In the 2000s, DiCaprio did his best to separate himself from the teeny bopper roles that he’d been saddled with in the ‘90s. He took some left turns and had some flops along the way, but things definitely worked out.
This is truly a photo of young love. Vanessa Laine, was only 18 years old attending Marina High School when Kobe proposed and then a month later took home the first of his five championship rings in June of 2000 (pictured).
Bryant met Laine when he stopped by the filming of a hip hop video where his future fiancé was acting as a background model. The two hit it off and were inseparable from then on out.
After winning his first NBA championship, Bryant and his fiancé skipped her prom and instead went to Italy to celebrate. That's not a bad way to start off the decade.
After tying the knot at St. Edward Roman Catholic Church in 2001, Kobe and Vanessa began a long, and tumultuous journey as a couple. Kobe’s parents didn’t attend the wedding, and neither did his agent, which made it look like the union was off to a less than auspicious start.
Even so, in 2002 the couple moved into a $4 million home in Newport Beach while Kobe continued to dominate with the Lakers. His estrangement from his family ended just a year later when the couple’s first child was born on January 19, 2003.
The couple was one of the most revered of the 2000s, even if they had their ups and downs. Sadly, just as Kobe started growing into an all-star dad and husband, tragedy struck on January 26, 2020, when his helicopter crashed killing him, his daughter, and several others. Impromptu memorials to Bryant went up around the world shortly after the news was announced.
General consensus says that a decade tends to stretch out for a few years past its welcome. The early ‘90s look like the late ‘80s, and the early aughts look like the late ‘90s. So it makes sense that the final coffin nail in the ‘90s was hammered in 2005 when Brad Pitt and Jennifer Aniston officially announced their break up.
The star crossed celebrities got together in the late ‘90s, and rumors of their break up began in 2004 after reports that Brad was hooking up with Mr. And Mrs. Smith co-star Angelina Jolie. In January 2005 the couple released a joint statement announcing their divorce. It read in part:
For those who follow these sorts of things, we would like to explain that our separation is not the result of any of the speculation reported by the tabloid media. This decision is the result of much thoughtful consideration. We happily remain committed and caring friends with great love and admiration for one another.
The divorce would not be finalized until October of that year, by then Pitt was reportedly already dating Jolie.
The events of September 11, 2001, were some of the worst moments in American history. When the Twin Towers were brought down by terrorists no one knew what was happening for what felt like an eternity, it was just clear that our way of life was changing forever.
Professional skateboarder Jason Dill was in Manhattan on the day of the attacks on New York and according to his friend Mike Piscitelli the two of them were just waking up and walking outside when the planes hit the building. They were hungover and in a state of shock, there was no way to know the magnitude of the moment in which they were living.
Today, there’s really only a couple of cell phone styles, but in the 2000s consumers were inundated with all different types of designs - from flip phones, to sliders, Blackberries, and Sidekicks. It was the Wild West of cell phone technology basically.
When this Forbes cover was released it makes sense that Nokia was seen as the leader in cell phone technology. Apple had only released their first iPhone in 2007, and Nokia had at least a decade on them in terms of market saturation.
It’s fascinating to see how off base this magazine cover was, but we totally get why they put it out.
Kylie and Kendall Jenner show off their fashion status on Halloween, 2000
Growing up as a Kardashian can’t be easy, especially when you’re a Jenner, but for Kendall Jenner things were tough because she felt like she didn’t stack up to her sister - especially in middle and high school but she didn’t have as many friends as Kylie.
In an interview with ZAZA WORLD RADIO, on Beats 1, Kendall explained that while she has a vast social life now, that she spent much of her teens at home moping around because she was so unpopular:
I was sitting in my room a lot of days crying because Kylie had so many friends, and I didn’t know what to do, and it’s gonna make me emotional right now. I really was like, ‘I’m never gonna have friends.’
Britney Spears and Leonardo DiCaprio flash gang signs, 2001
In what crazy world were Leonardo DiCaprio and Britney Spears hanging out? They’re from two entirely different universes of celebrity - He’s a star of the big screen who pretty much only does important films and she’s a pop star who’s famous for wearing a school girl uniform and a giant snake.
The only time something like this was the 2000s, an era when pop culture was thrown into a blender and mixed up until everything was happening at once. That being said, of course these two huge stars were in each other’s orbit. They’re both attractive and popular (and super famous).
It’s not entirely clear when this photo was taken, but if anything sums up the first decade of the millennium, it’s this one.
It’s unfortunate that we lost so many stars in the 2000s, but one of the most startling deaths occurred following Heath Ledger’s turn as the Joker in Christopher Nolan’s The Dark Knight.
Ledger is absolutely electric onscreen, and according to his co-star, Christian Bale, Ledger pushed him to the edge while filming. But Bale is quick to note that when Ledger was out of his makeup he was just a regular guy. He explained:
Our first scene was in an interrogation room together, and I saw that he’s a helluva actor who’s completely committed to it and totally gets the tone that Chris [Nolan] is trying to create with this. We’re not going for actors revealing their enjoyment of playing a wacky caricature. We’re treating this as serious drama. You go into character and you stay in the character. I love that. I find that so ridiculous that I love it, and I take that very seriously. Heath was definitely embracing that. When he was in the makeup and the garb he was in character the whole time; and when he took it off he was absolutely fantastic company to be around.
The Office is easily one of the most beloved sitcoms of the 2000s, but no one knew how popular it would be during pre-production or even in its truncated first season. Based on a beloved British sitcom, the series shows the mundanity of office life, which isn’t exactly what you think of when you think “hit TV show,” but the cast and crew proved viewers wrong.
Everyone on The Office is essentially beloved television royalty at this point, and to make sure that they hired actors who the audience could connect with the producers did something unique during casting - there was no script.
Instead, prospective cast members were asked to answer questions in character. Jenna Fischer says that in order to nab the role of Pam she made sure that she was as boring as possible.
After an extremely successful run as a centerfold and TV star throughout the ‘90s, Pamela Anderson slowed things down in the 2000s. At the time she was dealing with the fallout of her divorce from Tommy Lee and raising her kids, something that she was really looking forward to:
I needed to take a break. Nothing I attempted to do while the boys were growing could get my full attention. I did a lot of short runs. And always wanted to be at home. I wouldn’t miss a baseball game. My kids schedules were in my contracts.
Even while she was laying low in the 2000s Anderson was still extremely popular. Why wouldn’t she be? She’s Pamela Anderson.
Jim Carrey's 'Grinch' transformation took hours to complete every day, and it put the film's head makeup artist into therapy
Ron Howard’s How The Grinch Stole Christmas has become a holiday classic for people who grew up in the 2000s, but the set was anything but cheerful. Carrey had to sit in makeup for hours every day to become the Grinch. He was covered head to toe in green fur and wear elongated contact lenses. It was hell, and he made sure everyone on set suffered with him, but no one suffered more than makeup artist Kazuhiro Tsuji.
At one point in filming Carrey destroyed a day’s worth of work when he got tired of wearing his costume. Tsuji explained:
On set, [Carrey] was really mean to everybody and at the beginning of the production they couldn’t finish. After two weeks we only could finish three days’ worth of shooting schedule, because suddenly he would just disappear and when he came back, everything was ripped apart. We couldn’t shoot anything.
Tsuji finally had to step away from the project for a few weeks while Carrey was told to keep his temper in check. The experience was so grating that Tsuji ended up entering therapy after returning to finish the film.
Cameron Diaz and Drew Barrymore before the premiere of 'Charlie’s Angels: Full Throttle' in New York June 2003
There’s no franchise from the 2000s that’s quite like the duology of Charlie’s Angels. Initially thought of as a lark, the series starring Drew Barrymore, Cameron Diaz, and Lucy Liu, wasn’t just capitalizing on the girl power of the ‘90s, but it showed that action movies didn’t just have to be about gruff guys with chips on their shoulders.
The films were produced by Drew Barrymore, who after decades of ups and downs in the film industry was finally showing that she was a talent not to be ignored. She told W:
It’s not often that a girl gets the chance to produce an amazing high octane franchise. That’s a lot of pressure, because there’s a lot of money, but you also get to make stories where girls get to kick butt yet support each other, and love each other, and want to laugh with each other, and want to go on dates at night and then talk about the dates while they’re in the middle of everything else. They’re just girls with a great capacity for fun and a wicked sense of humor. And to live in that world for five years straight was really a blessed thing for me.
Anna Nicole Smith, Courtney Love and Avril Lavigne in Las Vegas, September 2004
The 2004 World Music Awards after party in Las Vegas must have been off the chain. Lavigne was riding high after taking home awards for World's Best Pop/ Rock Artist and World's Best-Selling Artist: Canada, as well as her then-recent hit single “My Happy Ending,” while Love was cutting loose after the release of her first solo album.
To be a fly on this table, you know? We honestly can’t think of three people who have less to do with one another. At least Lavigne and Love can chat about the music business, but what would Smith have to add to the conversation.
Unfortunately, Smith passed away in 2007 so we’ll never really know what was going on here.
Keanu Reeves in Paris, 2003
After a legitimately stunning career turn in the ‘90s where he went from playing a dumb metalhead, to an action star, and then starring in one of the most groundbreaking films ever made, Keanu’s 2000s were a little more quiet, but that’s not accidental.
After spending a year and a half filming two Matrix sequels in the early 2000s Keanu just shut down for a while. He told Rolling Stone that the physical demands of the sequels were much greater than the original and the experience drained him:
Before, we fought one at a time, and I know that they want me to do five. Which is master. That’s the real deal. If you can fight five people, that’s Jackie Chan, Bruce Lee stuff. So you need a whole other technique for that. You need a whole other level of proficiency, to be able to film close to real time and to be consistent and to have power on blows and to sell the punches.
Wouldn’t you go to Paris to relax after a work schedule like that?
Beyoncé in Juicy Couture with her bodyguard Teen Vogue, 2004
For many people growing up in the late ‘90s and the 2000s there is no world without Beyonce. With Destiny’s Child, she helped changed the way that music fans thought about girl groups, but with her solo debut in 2003 she ascended to the vaulted stage of a true pop star.
With “Dangerously In Love” the world was introduced to a new kind of pop star, a woman who was ready to take the world by storm while creating music that everyone could enjoy, not just teenagers. Beyonce explained that the thing that made her so popular was her consistent songwriting. She told Rolling Stone:
This is not something anybody planned for me. I had the help of my family, I don’t do it all by myself, but I write my songs, I write my treatments, I help with my clothes. Anybody who, every time they’re seen they’re right — it’s not other people. You can’t be that consistent without the artist being involved.
Lebron James at Monday Night Raw, 2003
Two things exploded in the 2000s, Lebron James and professional wrestling. Sure, wrestling’s popularity comes in waves but after slowing down a bit in the late ‘90s it made a come back in the early 2000s. One of wrestling’s biggest fans is none other than Lebron James, an inarguable giant in the world of basketball.
James is such a big fan of wrestling that he’s posed with a championship belt, released a pair of Nikes that were inspired by Ric Flair’s robes, and actually reached out to the Nature Boy to let him know that he’s the “inventor of swag.”
Mariah Carey shows off her Hello Kitty themed bathroom
In the 2000s, Mariah Carey went from glamorous pop star to sort of a modern day Howard Hughes. She never lost the pipes that made her a star, but the rigors of the music business weighed on her, making less interested in going out into the world to deal with its myriad stresses.
If you were dealing with entertainment industry based trauma wouldn’t you want to set up your home to be exactly what you want it to be, Hello Kitty bathroom and all?
The heavily decorated bathroom is just one section of a triplex penthouse apartment that’s covered in gold and pink. Aside from the color scheme Glamour reported at the time that Carey’s home was also covered in family photographs.
One of the most iconic moments of the 2000s occurred at the 2003 VMAs when Britney Spears kissed Madonna onstage at the end of their live performance. When people think about this infamous moment they focus on the kiss, obviously, but there was a lot more happening than just a smooch.
Not only was Christina Aguilera on stage with the women, but she kissed Madonna as well. MTV in’t show that and instead cut to Britney’s ex, Justin Timberlake who was… less than enthused about the whole thing.
Even though the entire moment was built to foster drama, it pretty much defined the 2000s and the way pop stars handled themselves. If they weren’t getting attention then what was the point?
Scarlett Johansson has been tantalizing audiences for decades, and even though she’s one of the most famous actors on the planet today thanks to the MCU, she spent the early 2000s as a kind of twee heart throb, this is mostly thanks to Lost in Translation and Ghost World.
When Sophia Coppola was putting together the cast for Lost In Translation the first actor she reached out to was Johansson, then she built the film around her. She explained:
She had that husky voice even then and seemed mature beyond her years. There was some quality about her that stood out and I connected with. She’s able to convey a lot without saying anything. I had a feeling about her. I wasn’t surprised she went on to do lots of different things after but I’m surprised when I look back at how young she was.
An iconic red, white, and blue Rolling Stone cover featuring Britney Spears
In 2000, Britney Spears showed that she had staying power beyond her bubble gum pop fantasy “Hit Me Baby One More Time.” Rather than take a severe left turn or become a “serious artist,” Spears grew up just enough and carved out her spot on the pop version of Mount Rushmore with “Oops!… I Did It Again.”
Weird punctuation aside, the album and its four singles cemented Spears as the pop princess to reckon with, and it turned her from teen dream into a legitimate pop star.
Spears knew that this follow-up was important, and that’s why she went into the studio to record the album six days after getting off tour for her first album.
Heath Ledger with daughter Matilda in Brooklyn, 2007
Audiences really only know Heath Ledger from his roles in films like The Dark Knight and Brokeback Mountain. He was an intensely private actor who did his best to separate his public persona from his young family.
According to everyone who knew him, Ledger was a great dad. When Michelle Williams was pregnant he made sure that she didn’t feel bad about herself by chomping down on pizza and ice cream with her and putting on 20 pounds.
Ledger and Williams went back to eating healthy after Matilda was born, it’s too bad that he wasn’t able to see her grow up.
Lil Kim, Britney Spears, and Mariah Carey in the TRL photo booth, 2001
Aside from chumming it up with Carson and waving to fans from the TRL Live studios in downtown Manhattan, the one thing that stars were expected to do was sit down in the photo booth and strike a pose. If you were a pop star coming through the building you had to sit down and show your best sides for the MTV audience.
Pretty much every star that sat down in the booth took as many goofy photos as possible. They were playful and excited - it’s clear that most of them were enjoying their first 15 minutes of fame, and not even thinking about whether or not the next 15 minutes were on their way.
A rare casting Polaroid of Doutzen Kroes from 2003
It’s rare to see such an off the cuff photo of a model. They’re so often posed and well lit that they don’t seem like real people, they’re more like constructs. By the 2000s the era of the super model had crested, but Kroes took the world of Victoria’s Secret by storm when she was only 18 years old.
Kroes says she never wanted to be a model, but after some shots of her were sent over to Paparazzi Model Management in Amsterdam her career was jumpstarted in a major way.
Before that twist of fate she was a country girl, biking 15 miles a day to school and back from her home and hanging out with horses. It’s a long way from that to fashion week.
After spending the ‘90s as one of the most desired women in genre films, Salma Hayek took the 2000s by storm with massive roles in films like Frida and Once Upon a Time in Mexico, but aside from these beloved roles she was a constant on red carpets across the world.
Hayek’s 2000s filmography may be light, but that’s because she spent much of her time trying to get Frida off of the ground, something that she’s extremely proud of, as well she should be. She explained to In Style:
I was nominated for an Oscar for my performance in Frida at the time. I had to fight for eight years to get Frida off the ground. Nobody wanted to make a story about a Mexican Communist artist with one eyebrow. It was really hard. But I had a vision for it. And I’m proud that I produced it too. There was no ‘Oh, can I please have a credit?’ No, no, no. I made that happen.
Jim Carrey and Kate Winslet on the set of ‘Eternal Sunshine of the Spotless Mind’, 2003
There’s no movie that took hold of the 2000s quite like Eternal Sunshine of the Spotless Mind, the film about a man who decides to erase his ex girlfriend from his brain. With a heartbreaking story and amazing direction by Michel Gondrey, this is one of the few films from the twee era of the 2000s that still holds up.
Winslet believes that Eternal Sunshine is the reason that she was offered serious roles after her turn as a teen star in films like Titanic:
I think creatively it opened people’s eyes to other sides of myself as a performer. I think that perhaps if it hadn’t been for that, maybe I wouldn’t necessarily have been considered for something like The Reader. I was able to show my versatility in Eternal Sunshine, and versatility obviously expands in all kinds of different directions.
Adriana Lima in the middle of setting a record for most appearances on the cover of GQ
Considered to one of the most beautiful women on the planet, Adriana Lima got her start with Victoria’s Secret in 1999, and throughout the decade she earned the vaulted title as one of the “new supers,” a rare group of young women who rose out of the dregs of the models of the 2000s to take over the world.
Even if you don’t keep up with the world of fashion you’ve seen Lima in one aspect of your life or another. She’s modeled for everyone from Maybelline, H&M, Fendi, and so on and so forth.
By 2008 she set a record for the amount of times a woman has appeared on the cover of GQ and ranked as the world's fourth highest paid supermodel by Forbes Magazine.
'10 Things I Hate About You' style icon Bianca Stratford
10 Things I Hate About You is kind of the Rosetta Stone for millennials when it comes to fashion, music, and weirdly enough Shakespeare. The film is basically a remake of The Taming of the Shrew but with a 2000s edge that introduced young audiences to Heath Ledger, Julia Stiles, and a young Jospeh Gordon Levitt.
Sure, he was in Third Rock From the Sun, but this is the movie that made him viable as a big screen actor.
Most of the actors in the film went on to be big names, but Larisa Oleynik who plays Bianca Stratford took a circuitous route to cult status. She went on to appear in Mad Men as well as a ton of independent productions.
Angelina Jolie and Brad Pitt with their children, March 2008
One of the most important stories of the 2000s was relationship between Angelina Jolie and Brad Pitt. After meeting on the set of Mr. And Mrs. Smith, the two formed a partnership that destroyed one of America’s most beloved couples and introduced the world to the concept of stars adopting A LOT of kids.
Aside from adopting multiple children, in 2008 Jolie gave birth to twins Knox Leon and Vivienne while the couple was staying in Nice, France.
Photos of the twins allegedly sold for $14 million to People magazine, which the family used to fund the foundation that they created to help children in need across the globe.
A young Brittany Murphy cheeses for the camera
Seeing the adorable face of Brittany Murphy from the ‘90s really makes you think about what happened to her in the 2000s. She was riding high on the success of Clueless, Riding In Cars With Boys, and 8 Mile, but as the 2000s wore on her career dipped.
It’s not that she stopped working, it was the opposite. Murphy appeared in at least one movie a year until she passed away in 2009 from a combination of pneumonia and anemia and a toxic cocktail of prescription drugs.
The loss of Murphy was a huge hit not only to Hollywood, but to movie lovers everywhere.
Emma Watson & Tom Felton at the 'Scooby Doo' premiere, 2002
The kids of the Harry Potter series grew up in the public eye. Locked into a solid eight films, Daniel Radcliffe, Emma Watson, Rupert Grint, Tom Felton and the rest of them were the talk of millions of fans, but Felton says that the fame game wasn’t as great as it was chalked up to be:
One thing that people keep on saying to me is that the wealth and the fame must have made up for missing out on my childhood. But the idea of money — putting a price on your childhood — is ridiculous. You will never get those years back and you can’t put a price on them. And to me, fame is not a positive thing. The idea of being famous is a lot better than the reality. It’s fantastic when you go to premieres and people cheer you, but it’s not real. And it’s totally not my approach to get my name on a club door just because I can.
All of the kids from the Harry Potter series dipped out of the spotlight after finishing the films, even the actors who weren’t as famous as Radcliffe and Watson must have felt that they needed a break.
Drew Barrymore, Lucy Liu and Cameron Diaz ‘Charlie’s Angels’, October 2000
One of the greatest films of the aughts was Charlie’s Angels - the maximalist, over the top action film that didn’t have much of a plot but that didn’t really need one.
The film is excessive, but it’s not like it’s trying to be a little indie movie or anything. Rather than try to pretend that it was something that it’s not, 2000’s Charlie’s Angels takes everything about the original series and blows it out, makes it bigger, and gives the audience what it wants.
Charlie’s Angels is relentlessly positive, which makes sense because it’s produced by Drew Barrymore and she doesn’t have a frowny bone in her body. If you haven’t this movie in a while you’ve got to find a VHS of it right now.
Paris takes her flip phone and makes it fashion
Paris Hilton holds a unique place in the hearts of millennials. Not only did she coin the much quoted phrase, “that’s hot,” but she created a character based on the belief that she was, like, a totally vapid rich girl. Or maybe she was just being herself.
In the 2000s she was the one socialite who everyone knew. She was flashy and in your face and she didn’t care who she ticked off. Her style can be described as “bad taste,” but that was kind of her thing. She essentially created having a personal brand before having a personal brand was important to social media stars.
Looking back at Paris' style from the 2000s, it's clear that she formed the entire basis of the in your face, mish-mash style of the decade.
Kanye West showing off the Roc, 2000s
The world of hip hop changed completely in the aughts thanks to Kanye West. He single handedly changed the sound and vision of rap music with a series of albums that dragged hip hop from the streets to the suburbs with albums like “The College Drop Out” and “Graduation.”
Aside from making pink polos and vocoders cool to use in hip hop, he also embodied the duality of rap music. He was both obsessed with bling and he wanted to give back to society. He rapped about having ice on his wrist and worried about where the ice came from.
No one had a more bombastic 2000s than Kanye. He had insanely popular hits, he interrupted Taylor Swift at the 2009 VMAs, and he single handedly made Jamie Foxx into a beloved guest verse singer - and that was before the 2010s got underway.
Ryan Gosling and Rachel McAdams in Toronto, August 2008
If you were around in the 2000s, chances are you’ve had to sit down and watch The Notebook at one point in time, whether it was on a date or you just didn’t have anything else to do for a couple of hours. The biggest takeaway from that movie is the insane chemistry between Ryan Gosling and his co-star Rachel McAdams.
The couple actually met on the set of the film, but they were initially at odds with one another. It didn’t take long for the two to begin seeing one another after spending all day falling in love in front of the cameras, but in spite of their status as one of the most beloved couples of the aughts, their love was not to last.
While speaking with The Times in 2011, Gosling says that there was no horrific fight and no big breakup, they were just incredibly busy. He said:
Show business is the bad guy. When both people are in show business it’s too much show business. It takes all of the light, so nothing else can grow.
Michael Gary Scott ‘Stress Relief’ The Office, February 2009
There may not be a better character on 2000s television than Michael Scott from The Office. Not only was he the anchor of the show’s comedic sensibilities, but he was just so much fun to watch, which is why it was heart breaking when he left the show for good in 2011.
At the time it felt like it was time for him to say goodbye, but behind the scenes Steve Carrell was essentially forced to leave the show when NBC refused to make him an offer to stay. Casting director Allison Jones explained:
As I recall, he was going to do another season and then NBC, for whatever reason, wouldn’t make a deal with him. Somebody didn’t pay him enough. It was absolutely asinine. I don’t know what else to say about that. Just asinine.
Just think how amazing it would be if Michael Scott had been able to last until the very end. That's what she said.
Shawn and Marlon Wayans at the 'Scary Movie' Premiere, 2000
After the meta-slasher heyday of the late ‘90s there had to be a reckoning, a change of the guard, something to cult slasher films like Scream and I Know What You Did Last Summer down to size, and it came in the form of Scary Movie.
Starring Keenan Ivory and Marlon Wayans, Anna Faris, and David Cross, this horror movie spoof was a watershed events for comedy-horror fans, or just kids who were a little too afraid to watch, well, scary movies.
Released in the summer of 2000, Scary Movie destroyed box office records and created a franchise that people still love. While the Wayans family was more than ready to get ridiculous for this franchise, star Anna Paris says that she was incredibly nervous to be in the movie. She told Entertainment Weekly:
Keenen told me two amazing bits of advice. One was that there’s no vanity in comedy, and two, don’t wink at the audience. You have to be willing to embrace the idea that the audience is going to think you’re an idiot. That was an important lesson to me.
Missy Elliot rocks her trash bag outfit onstage
There’s no one that’s as groundbreaking in terms of musical endeavors or fashion as Missy Elliott, the Virginia born rapper and producer. The public first came to know her in the late ‘90s, but this four time Grammy winner continued to deliver game changing music throughout the 2000s and into the 2010s.
Elliot is a low key style queen, but her most iconic outfit has to be the trash bag suit from “The Rain (Supra Dupa Fly), something that the rapper says that she wore to hide her shyness while remaining the center of a conversation:
To me, the outfit was a way to mask my shyness behind all the chaos of the look. Although I am shy, I was never afraid to be a provocative woman. The outfit was a symbol of power. I loved the idea of feeling like a hip-hop Michelin woman. I knew I could have on a blow-up suit and still have people talking. It was bold and different. I've always seen myself as an innovator and a creative unlike any other.
Kendall and Kylie Jenner ‘Keeping Up With the Kardashians’ viewing party in Los Angeles, October 2007
It can’t be easy to be a pre-teen and watch as your life goes from semi-normal to TV fantasy essentially over night. Kendall and Kylie Jenner weren’t the stars of Keeping Up with the Kardashians when the series premiered, but audiences have watched them grow up since its debut.
While speaking with Vogue in 2015, the sisters say that life in front of the cameras is all they really know, even if it’s kept them from being normal teenagers. Kylie and Kendall are very business forward, which just comes with the territory when you’re some of the youngest billionaires on the planet.
Lil Bow Wow, a decade before he dropped the "Lil"
It’s strange to think about how stars who felt like they were everywhere in the 2000s fell by the wayside as the decade went on. Bow Wow, then going by Lil Bow Wow, was posed to be a massive star when he released his debut “Beware of Dog,” in 2000.
Produced by Jermaine Dupri, Lil Bow Wow had everything he needed to become a long lasting hip hop sensation. The album went double platinum, he rubbed elbows with hip hop luminaries like Snoop Dogg, and he was tapped to star in the films Like Mike and The Fast and The Furious: Tokyo Drift. So why did he drop off?
After his second album (which also went platinum) he dropped the “Lil” from his name in an attempt to be taken more seriously. That didn’t really work the way he hoped and his musical career went the way of the Milli Vanillis of the world.
If you’re taken aback by seeing the “Wrecking Ball” singer look downright wholesome then you’re not the only one. Cyrus spent her 2010s bleaching her hair and getting tatted up but in the 2000s she was a sweet Disney star. Or at least that’s how it seems.
Cyrus has said that when she was starring in Hannah Montana she was just clocking in and clocking out. Not because she didn’t enjoy the work, but because she was born into the industry and realized it was a job very early on. She explained:
I was an adult when I was supposed to be a kid. So now I'm an adult and I'm acting like a kid… My parents always had money, and I've always been around this industry, so I didn't have my mind blown or become obsessed with being famous.
Paul Walker and Jessica Alba ‘Into the Blue’, September 2005
The 2000s were all about bring the X-Treme sensibilities of the ‘90s to the mainstream, that’s how we ended up with the Fast and Furious and xXx franchises, but audiences were inundated with a ton of movies about surfing, skateboarding, and yeah, X-TREME SALVAGING.
Into The Blue stars a bevy of 2000s actors who are trying to make something out of nothing, including Paul Walker, Jessica Alba, Scott Caan, and Josh Brolin, and even if the movie doesn’t totally hold up it’s a lot of fun to watch these actors work with one another.
While speaking about the film shortly after its release, Alba explained that she helped shaped the end of the film with her action chops:
In the original script, at the end of the movie, Paul comes and rescues me. I do nothing for the last quarter of the movie. I told the director and said you know I can do action. I'm the most experienced person here. I mean girls don't really want to see girls get rescued all the time. I came up with all the action scenes at the end and got an action coordinator to cut them together.
Ray J & Lil Kim chilling after recording "Wait A Minute"
Most people know Ray J as Brandy’s brother and as the star of a very prominent private tape, but he’s also a rapper and reality TV star. In the 2000s he was poised to hit it big with the Lil Kim duet “Wait a Minute” which was produced by The Neptunes. Ray J says that even though the song was his single, Kim worked harder on the track than he did:
Lil Kim she really works hard, and you know I watch and I learned… She was in there six, five in the morning getting ready, and you know I was still asleep, getting out of my car at like 11. She was focused, determined, and she just wanted to make it high for herself.
Sarah Michelle Gellar and Freddie Prinze Jr. at the Knicks vs Miami Heat NBA Playoffs game in New York, May 2000
This may be the most 2000s couple ever, and weirdly the most successful. After working together on I Know What You Did Last Summer, Gellar and Prinze became one of the decades it couples, starring in two Scooby Doo movies together and then starting a family.
While other 2000s couples fell by the wayside, Gellar and Prinze managed to stay together by keeping out of the public eye. Gellar explained:
The number one specific thing is keeping our relationship to ourselves and having a relationship that is not out in the public. And because we don’t put it out there, because we don’t flaunt it, people respect that privacy and we’re given that. And that has given time for our relationship to grow and it gives us a life that we feel is separate from what we do for a living.
One of the biggest stories of the 2000s was the rumor that Paris Hilton went to a party at the Palms Hotel in Las Vegas on April 15, 2005, wearing a shirt that read “Stop Being Poor.” It was the perfect 2000s story and proof that Paris Hilton was as vapid as people had assumed, but it wasn’t true.
In reality, Hilton’s shirt read “Stop Being Desperate,” which is right in line with her brand, but after a Photoshopped version of the tank top leaked it was nearly impossible to dispel the rumor.
Hilton may have been the biggest villain of the 2000s simply because people wanted to hate her. Millennials and Gen Z have come to appreciate Hilton, but at the time she was public enemy number 1.
Young Jake Gyllenhaal❤️
Has Jake Gyllenhaal ever looked so young? Today we know him as an actor who takes on roles that scratch his dual itches of artistry and transformation, but when he was a young, hungry model/actor were the same things important to him? Apparently so, he told W:
I’ve been offered a lot of different things like this, but none of them felt genuine and authentic to me. And Calvin Klein allowed me to do something creatively.
Gyllenhaal’s big break was the cult classic Donny Darko, but he made the 2000s his own with stand out performances in Brokeback Mountain, Zodiac, and Jarhead, and he’s still making interesting choices today. Still, we can’t get over his baby face in this shot.
