This picture is somewhat out of the left field for us. Though seemingly from completely different Hollywood branches, it isn’t completely out of the realm of possibility that the two young stars would have crossed paths.
When this picture was taken, Spears was at the height of popularity after smash hit “Hit Me Baby One More Time” and DiCaprio as teen heart-throb after “Titanic’s” release in 1998. We think this bizarre duo sums up the early 2000s pretty nicely.
28-year-old Angelina Jolie Slaying as Laura Croft
When you think of the early 2000s, there are a few celebrity faces that are bound to come to the forefront of your mind. Leonardo DiCaprio, Kate Winslet, Matt Damon, Brad Pitt, and of course, the incomparably beautiful Angelina Jolie. In 2003, the popular video game Tomb Raider was developed into a movie, and Jolie won the prize role of Laura Croft.
It’s become common practice in today’s movie landscape for an actor to physically prepare for a role. Intense training sessions, nutritionist, the whole shebang; however, Angelina was one of the first female early adopters of this practice. Let’s be real; it worked. She is absolutely slaying in the silver bodysuit.
From Braniston to Brangelina
We are surprised each year, time and time again, by the most unpredictable celebrity breakups. The ultimate early 2000s power couple is and forever will be Brad Pitt and Jennifer Aniston.
Pitt and Aniston were America’s Sweethearts, so the public was shocked when they announced their divorce following rumors of a fling between Pitt and "Mr. & Mrs. Smith" co-star Angelina Jolie. In 2005 the couple released an official divorce statement and thus commenced the saga that led to the moniker "Brangelina," Pitt, and Jolie marrying and consequently becoming parents to six, count ‘em, six children.
Tyson’s Brand Is Created - 2003
Boxing legend and wild card Mike Tyson made quite a comeback in the early 2000s after a several-year lull in his career. What can now be considered his most identifying mark, the idea behind Mike Tyson’s famous face tattoo actually stemmed from a self-destructive place.
In an attempt to destroy his own image by tattooing his entire face, Tyson was saved, in a sense, by an artistic vision. Tyson’s tattoo artist suggested the Maori tribal design, which can to this day be instantly associated with the boxer and his brand.
A Kardashian/Jenner Moment of Normalcy
In a world deeply saturated with the lives and doings of the Kardashian/Jenner clan, it’s hard to remember a time when the world’s most-watched and followed family was slightly less in the limelight.
Though nothing about their childhood compares to that of the average American, still we find moments of normalcy in an exceedingly less-than-normal life. The picture depicts Kendall and Kylie dressed for Halloween before becoming what we recognize today to two still very young yet extremely successful entrepreneurs and models.
Dicaprio and Spears: An Unlikely Duo - 2001
This picture is somewhat out of the left field for us. Though seemingly from completely different Hollywood branches, it isn’t completely out of the realm of possibility that the two young stars would have crossed paths.
When this picture was taken, Spears was at the height of popularity after smash hit “Hit Me Baby One More Time” and DiCaprio as teen heart-throb after "Titanic’s" release in 1998. We think this bizarre duo sums up the early 2000s pretty nicely.
Heath Ledger: A Talent Forever Missed - 2008
May we take a moment of silence for the incredible and incredibly handsome Heath Ledger, gone way too soon. We shockingly lost him in 2008 after the young star wowed audiences with his incredibly dark interpretation of the Joker in Christopher Nolan’s “The Dark Night.”
Ledger delved deep into the psyche of his character, making for an absolutely unforgettable performance. As much as we appreciate the work he did as the Joker, we’d like to remember him in our absolute favorite scene in “10 things I Hate About You,” where he sings “You’re Just Too Good To Be True” to Julia Styles on the bleachers.
The Office First Table Read - 2004
"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 during its truncated first season. Though based on a beloved British sitcom, the US version became an instant classic, to be quoted for years to come.
The show shot some of the actors to instant stardom (i.e., Steve Carell, John Krasinski, and Mindy Kaling) and created TV royalty from the cast. This kind of makes us want to rewatch the whole series; excuse us while we go binge all the seasons real quick!
Lady in Red: Pamela Anderson on Jay Leno - 2002
Pamela Anderson is primarily known as the busty broad from "Baywatch," who would run in slow motion in that iconic red suit. The early 2000s for Anderson was a time to slow down and focus on raising her kids after having had huge success in the 90s as a centerfold and very popular TV star.
Slowing things down and taking a step back from her career was ideal for Anderson, who wanted to be a present parent and not constantly hopping around between gigs. An extremely admirable move for the well-known star.
A Grinch on and off Screen: Jim Carrey
If you’re a 90s kid, you had the privilege of growing up with both the original cartoon version of “How The Grinch Stole Christmas” and were there for the release of the wacky Jim Carrey live-action version in 2000.
The wild makeup for The Grinch was hyper-realistic and took several hours to be applied. Carrey’s makeup artist Kazuhiro Tsuji described the labored process as taking quite a toll, having several disputes with the agitated actor. In the end, though, the final product was quite impressive.
Girl Power and Girly Power: Charlie’s Angles - 2003
Though many may remember the original "Charlie’s Angels" (we’re still trying to understand how Farrah Fawcett got her hair to stay like that), '90s babes will always picture Drew, Cameron, and Lucy. The quality of the movie indeed left a little bit to be desired, though certainly holding large sentimental value, there is somewhat of a breakthrough here.
The movie, produced by Barrymore herself, highlighted the dichotomy of strong female empowerment in conjunction with the girly side. The two, it seems, are not mutually exclusive. It’s funny, action-packed, chock full of A-list actors, and just an all-around classic.
Young in Hollywood, Cruz, and Depp on Set - 2001
The movie "Blow" came out in 2001, starring a young and dashing Johnny Depp as a small-town kid to big-time dealer George Jung. Depp acted alongside newcomer Penelope Cruz who had only emigrated from Spain, having already gained quite a bit of success there.
The movie was extremely well received, and Cruz got her first real taste of Hollywood. Cruz would become quite a household name in the 2000s and continue acting amongst A-list stars until she became one herself.
Blondes Do Have More Fun: 2004
We can only imagine what it might have been like to party in Hollywood in the early 2000s. No Instagram stories, no live updates, no 1,000 photos documenting every second. This pic was taken in 2004 at the World Music Awards after-party in Las Vegas.
Avril Lavigne, at the height of her career, was celebrating her wins for World's Best Pop/Rock Artist and World's Best-Selling Artist: Canada. The three blondes (Anna Nicole Smith, Courtney Love, and Avril Lavigne) are the epitome of early-aughts style….who didn’t love a middle part back then?
Neo Takes a Break: Keanu Reeves in Paris - 2003
From “Bill and Ted’s Excellent Adventure” to the "Matrix," Keanu Reeves had a supremely successful start to his career. The young actor filmed three high-intensity action films from 1998 to 2003, resulting in a much-needed break from Hollywood after an excessive amount of physical work.
Reeves was put on a training regimen similar to that of Jackie Chan or Bruce Lee. Reeves, just after the release of the final "Matrix" film, is seen relaxing in Paris before starting season two of his career, keeping him an A-lister through the years.
Even Queen B. Wore Valore - Beyoncé 2004
Grew up in the late 90s? Destiny’s Child (but mostly Beyoncé). Grew up in the 2000s? Beyoncé. Grew up in the 2010s? STILL BEYONCE. A pop star of absolutely inconceivable status, Beyoncé grabbed the attention of fans right from the start as the standout star in the well-known girl group Destiny’s Child.
In 2003, she released her first solo single with now-husband Jay-Z, “Dangerously In Love.” The song was and remained a massive success. When Queen B. finally broke out as a solo star, her career completely took off, making her the pop/R&B icon we know her as today.
Basketball Star Turned Wrestling Fan: Lebron 2003
Though Lebron James is well known as a basketball star (physically and metaphorically speaking), he himself is a huge wrestling fan. In the early 2000s, the sport’s popularity was up and up after several years with diminished ratings.
James even paired up with Nike to create a limited-edition sneaker inspired by Ric Flair's robes. The basketball star can be seen in this pic holding what we’re sure must have been the latest cell phone technology at the time, the sturly ‘ole flip phone.
Who Said Hello Kitty Was for Kids?
Mariah Carey, whistle tone sensation and singer of the world’s most beloved Christmas song. The young singer shot to stardom in the late 90s/early 2000s. Who doesn’t remember that classic movie "Glitter"? We’re surprised it wasn’t nominated for an Academy Award!
The wildly successful pop star bought a triplex penthouse apartment with a gold and pink theme. One might think from the picture that this was her child’s Hello Kitty-themed bathroom. However, we’re here to set the record straight. This picture was taken well before the twins were born, meaning this was a design decision she made for herself as a woman in her early 30s….but who are we to judge?
Heartthrobs in Hollywood - DiCaprio, Depp, and Pitt
This photo is the OG "it-guys." These 2000s heartthrobs were all the rage in the 2000s (though we’d venture to say Brad Pitt aged like fine wine and is still top of the list). Johnny Depp was rocking his adorable Benny and Joon look while Leonardo DiCaprio was still enjoying the massive success of "Titanic."
This picture has too many chiseled jawlines and shiny, floppy hair for us to handle. We might as well be looking at a Calvin Klein ad here….excuse us while we leave to grab a drink of water...
Wonder Woman or Beyoncé Selling Pepsi? - 2003
In the early 2000s, Pepsi made a big move to surpass Coca-Cola as the most popular soda. The strategy was taking the biggest stars at the time and sponsoring them. The group was called “The Pepsi Gladiators” and consisted of Britney Spears, Pink, and Queen B herself, Beyoncé.
The commercial cost a small fortune ($3 million to be exact) and absolutely helped boost Pepsi’s popularity. Truthfully, if we didn’t have the lovely Gal Gadot as Wonder Woman today, we could certainly see a reboot with Bey.
Britney at Her Prime
In 2000, Britney Spears showed that she stayed power beyond her bubble gum pop fantasy, “Hit Me Baby One More Time.” Proving she had more hits in her arsenal, the pop princess subsequently released “Oops!...I Did It Again” with her iconic school-girl outfit and tight pleather jumpsuit.
The album and its four singles cemented her spot as a pop icon. Let’s be honest, who else could crush a look that consists of an American flag crop top and red bell bottoms?
A Beautiful Moment: Heath Ledger and Matilda 2007
An absolutely heartbreaking snapshot of Heath Ledger and daughter Matilda. The young 27-year-old was just beginning the height of his career and starting a family before the tragedy.
Ledger was an intensely private actor who did his best to separate his public persona from his young family. According to everyone who knew him, he was a great dad. We have no doubt about this. At least Matilda has all of the movies he managed to make to get a sense of just how talented her dad was.
Britney Spears on TRL 2001
What could be more 2000s than TRL? When stars came through the MTV stage in downtown Manhattan, it was a ritual to go through the screaming fans and sign whatever merch was there. Oh, and check out the people holding fan signs out the window.
MTV audiences lived for these appearances and for the chance to get a closer look at stars who for only a moment almost made them seem like just regular people. They are regular people but let’s be real; the average plebeian couldn’t possibly understand that level of fame.
From Amsterdam to Fashion Week - Doutzen Kroes 2003
An undeniably natural beauty, Doutzen Kroes took the modeling world by storm after paparazzi shots of her were sent to Modeling Management in Amsterdam. Although Kroes had never dreamed of starting a career in modeling, quickly made a name for herself, becoming a Victoria’s Secret Angel by the age of 18.
Kroes continues to work in the fashion industry and has even dabbled in acting. That being said, the high-profile model makes a point to instill in her children the importance of academia.
Sassy, Spanish and Slaying the red carpet - Hayak 2001
Our favorite Spanish actress, Salma Hayak, has been active in Hollywood for over 20 years. From "Frida" to "Once Upon a Time" in Mexico, the Spanish actress made her mark both on-screen and on the red carpet.
Hayak notes the movie "Frida" as her crowning achievement, not just as an actress but also has produced the film and worked tirelessly to push the project through to completion. A petite 5’ 2”, Hayak absolutely crushes in this tight halter, showing us that real women really do have curves.
Winslet and Carrey Break Their Stereotypes - 2003
In 2004 the iconic movie “Eternal Sunshine of a Spotless Mind” was released starring Jim Carrey and Kate Winslet. Carrey, having done mostly comedies, got to show his dramatic chops while Winslet was able to break out of her typecast as Rose from “Titanic.”
The movie was a massive hit being simultaneously relatable and surreal. Winslet claims the opportunity to do "Eternal Sunshine' ultimately opened the door to some of her more dramatic films, such as “The Reader,” by really spotlighting her versatility as an actress.
A Young Adriana Lima - Rising in Ranks
Though you may not know the name, you most certainly would recognize the face. Brazilian beauty Adriana Lima has made her mark on the modeling world throughout the years, now a veteran as a Victoria’s Secret Angel.
and quickly became one of the most recognizable faces amongst the top girls in the industry. In 2008, the striking model made a name for herself by setting the record for most appearances on the cover of "GQ."
Look No Further for 2000s Fashion Inspo
Let’s talk for a moment about the absolute cinematic masterpiece that is the movie “10 Things I Hate About You." An instant classic based on the Shakespeare play “The Taming of the Shrew,” the movie follows Julia Stiles as Kat, a smart yet standoff-ish high schooler who is ultimately charmed (and rightfully so) by the handsome bad boy Patrick played by Heath Ledger.
This was our first introduction to Ledger, and boy, what an entrance. In general, the whole movie is chock full of 2000s gems, like a young Joseph Gordon Levitt who finally made his move from TV to film. The pic is Larisa Oleynik sporting what can only be described as the latest 90s/early 2000s we could imagine.
Brangelina at the Height of Coupledom - 2008
Brangelina. Everyone knows the term. Everyone knows the couple. The early 2000s was a wild ride, from Brad Pitt and Jennifer Aniston’s split to him marrying Angelina Jolie and subsequently having/adopting six children together.
Though the superstars are known for their standout looks, the couple decided to help children in need was a calling they shared. While vacationing in Nice, France, the couple allegedly sold photos of their twins Knox and Vivienne for $14 million to "People" magazine and used the money to create a foundation that helps children in need worldwide.
Britney and the Tiger King - 2001
In 2001, Britney Spears performed her new single “I’m a Slave 4 U” at the VMAs. The performance was bombastic and big, as we know the pop star to be. As part of the whole shebang, Spears had live tigers on stage with her during the number.
The tigers were handled by Doc Antle, who, for those of you that might recognize the name, was a tiger seller in the hit Netflix series “The Tiger King.” We’re still waiting for Britney’s next single, but we have this wild performance to hold us over in the meantime.
Keep Smiling Brittany
Though her career was tragically cut short, Brittney Murphy made a name for herself in several standout roles. We remember her first and foremost as Ty, the bright-eyed and bushy-tailed newcomer in “Clueless.”
Post clueless gave us “Riding in Cars with Boys” and the Eminem classic “8 Mile.” There’s no doubt we all would have liked to see where her career headed. Since we can’t, however, this is how we want to remember her. Young, beautiful, and smiling.
Gryffindor and Slytherin Unite - 2002
The first Harry Potter movie was released in 2001. It’s sometimes easy to forget that the actors, now well into adulthood, were just 11 or 12 years old when the first film was made.
Though with fame comes a great deal of red carpet events and exciting premieres, it also brings with it a loss of anonymity. The beloved films were almost a decade in the making, and though certainly significant in our childhoods, they would shape the rest of the lives of the young stars forever.
Oh, the Charlie's Angels DRAMA - 2000
If you’re a 90s kid and think about "Charlie’s Angels," it’s Drew Barrymore, Cameron Diaz, and Lucy Liu that come straight to mind. The movie, produced by Barrymore, was action-packed and though some might disagree, we’d argue, didn’t take itself too seriously.
Audiences could enjoy silly jokes, inspiring female leads, and Sam Rockwell as a very cute villain. Let’s also not forget the incomparable Bill Murray as Bosley. Absolutely A+ casting. To be honest, it’s been a while since we’ve seen this one….maybe a movie night is in order.
Paris Hilton Channeling Twiggy
Serving us Twiggy circa 1966, Paris Hilton, heiress to the Hilton hotels fortune, was a prominent public figure throughout the 2000s. Love her or hate her, she built a personal brand and stuck to it.
The socialite was the epitome of young fashion at the time, no doubt making a name for herself in Hollywood….somehow without having any discerning talents… It’s not easy to know what to make of it, but if you want to get a glimpse into the early days of reality TV, we highly recommend watching just one episode of “The Simple Life.” Absolutely wild.
Kanye West Serving Face in the Early 2000s
From his breakout album “The College Dropout” and furthered by the critically acclaimed album “Graduation,” Kanye West made a permanent mark on the genre of rap. The young rapper had rhymes, beats, business savvy, and an ego that wouldn’t let him fail.
Though many know him now as an integral part of the Kardashian clan, the dare we say, very talented West started as a force to be reckoned with what we wouldn’t give to have another album from those early days. Pure genius.
When McAdams and Gosling Were the Dream Couple - 2008
We ask. What comes to mind when you think of romance movies? If the first movie isn’t “The Notebook,” we politely ask that you drop everything you’re doing and make yourself a bowl of popcorn.
Not only was this movie beautiful and absolutely heartbreaking, but co-stars Rachel McAdams and Ryan Gosling, who had an intense on-screen love affair, brought their relationship to real life. The couple quickly became one of the most beloved couples of the aughts. Though their relationship didn’t last, the breakup was amicable, and you can rest easy knowing each has since married and built families.
Classic Michael Scott (Carell) 2009
Name a more iconic TV boss…..we’ll wait. The hilarious Steve Carell showed his comedic genius through his last season on “The Office.”
Carrell’s nuanced acting somehow managed to turn a dim-witted character who was often out-to-lunch into an endearing one audiences were rooting for. Though Carell didn’t continue on through the final seasons of the show because of a dispute with the network, we can still enjoy full seasons of hilarity.
The Wayans Taken on Hollywood - 2000
After a slew of terrible (but also kind of amazing?) slasher movies like “Scream” and “I Know What You Did Last Summer,” it was only natural a parody would be made, and so happened “Scary Movie.”
The cult classic starred several newcomers who would go on to be supremely successful in Hollywood, such as Anna Faris, David Cross, and of course, the Wayans Brothers. The comedy duo is undeniably funny; however, we’d like to talk to their stylists, please. We absolutely require an explanation about that mesh turtleneck!
Trash Bags But Make it Fashion
Missy Elliot has been serving us groundbreaking hits from the late 90s and hasn’t stopped since. With each song came a look that only Elliot, being the true queen she is, could pull off.
The four-time Grammy winner brought music and style to a pique every single time. We’d argue that one of her most standout looks would be that of her trash bag suit from “The Rain (Supa Dupa Fly).” She is crushing the look even though we’re fairly certain she might have grabbed a few Glad bags right before she left to perform...
Pink Perfection - Halle Berry 2000
The MTV music awards gave musicians and Hollywood stars alike the opportunity to dress a bit outside the box. The red carpet style was slightly more casual, allowing this killer pink look from bombshell Halle Berry.
A LOT is going on here, from the bralette to the beaded fringe, to the sequins; there’s no doubt in our mind that very few could pull off this look. But hey, if anyone can do it, it’s gotta be our girl, Halle.
Kylie and Kendall: Tweens to Tycoons - 2007
It can’t be easy to grow up under such an intense magnifying lens. Though Kendall and Kylie weren’t initially the focus of “Keeping up With The Kardashians,” they certainly became central as the world watched them grow.
Life in front of the camera is really all the girls have known. The young entrepreneurs have continued growing their brand ever since the series has ended, becoming some of the youngest billionaires on the planet.
An Up and Coming Lil Bow Wow
Lil Bow Wow was on track to become a massive star when he released his debut album “Beware of Dog” in 2000. The album, produced by Jermaine Dupri, was double platinum, and the young rapper subsequently worked with Snoop Dogg and was tapped to star in “Like Mike” and “The Fast and the Furious: Tokyo Drift.”
After releasing his second album, which also went platinum, he decided to drop the “Lil” from his name. Now, who’s to say if this actually had any effect on his career? But, curiously, he dropped off pretty hard after that...
Sweet and Wholesome Miley at 16
Though we may recognize Miley Cyrus as the rebellious, tatted singer who stirs up the media, we should remember she began as a wholesome Disney star. Cyrus was familiar with the industry from a young age, exposed by her father, singer Billy Ray Cyrus.
The young Disney actress approached her work as a job early on, something not typical for child stars. We may be just venturing a guess, but this could be the reason her adult years brought with it the childlike rebelliousness she’s come to be known for.
Walker and Alba Serving Full 2000s Realness
The fast-paced action movie is never out of style but rather shifts with the time. The 2000s were a prime decade for extreme sports movies, such as the "Fast and Furious" franchise and a slew of surfing movies. Paul Walker was at the height of his career and was the one to cast for films in this genre.
The handsome actor had the perfect rugged/pretty boy look audiences were looking for. “Into The Blue” starred Walker and Jessica Alba, also one to watch at the time. The surf-film film didn’t receive the best reviews but honestly, who cares about the script when the actors look like that….
A Decadent Penelope Cruz - 2009
Inception on set, the movie “In Broken Embraces” focuses on the making of a movie within a movie. Spanish actress Penelope Cruz plays Lena, stuck in a relationship with former employer Ernesto Martel.
Martel, a wealthy tycoon, and control freak turn the former secretary into a successful actress. Cruz described the making of a movie within a movie as confusing at first, often mistaking cast members as crew members and vice versa.
True Love at Its Finest: Kobe and Vanessa Bryant 2000
At just 18 years old, Vanessa Laine snagged a young Kobe Bryant, who was one of the most successful and respected players in the NBA. The couple met on the set of a hip hop video in 2000, immediately becoming inseparable, and were married a year later.
Just a month after their initial meeting, Kobe took home the first of what was to be five championship rings. The couple had four children together before tragedy struck in 2020, resulting in the deaths of Kobe and his daughter Gianna. His legacy lives on, and we can revel in this picture that proves young love can last.
Classic Cuddling - Ray J and Lil Kim
Although often recognized as Brandy’s brother, Ray J had 15 minutes of fame (maybe a bit more) in the early 2000s. The rapper and reality star was slated to hit it big with the Lil Kim duet “Wait a Minute,” which was produced by The Neptunes.
Ray J was super impressed by Lil Kim’s work ethic. Although the song was ultimately his single, the rapper pegged Lil Kim as focused, determined, and someone to learn from.
The Start of Hollywood's Purest Couple - 2000
One of the most 2000s couples ever, Sarah Michelle Gellar and Freddie Prinze, are still together, more than 20 years later. They fell in love while on the set of "I Know What You Did Last Summer," and the rest, well, the rest is history.
While most Hollywood couples have called it quits, Gellar and Prinze managed to stay together. Their secret? Staying out of the public eye. They don't want to flaunt their love, but here we caught a glimpse of one of Hollywood's most successful couples.
A Surreal Moment Captured in Time - 2001
Jason Dill, a professional skateboarder, happened to be in New York City on September 11th, 2001, when the Twin Towers were hit. The shocked border is pictured here in front of the terrifying scene, almost in a dazed state, as can be said for much of the city and even word on that unexpected day.
Friend of Dill Mike Piscitelli captured the surreal moment, not yet fully understanding the magnitude of what had just happened. The two were just waking up when the planes hit, causing shock and dismay throughout the city.