How These 25+ Celebs Looked Like on ‘TRL’ vs. Today

The OG TRL host rocked a frosted tip hairstyle like nobody’s business. Back then, he was the king of MTV – the ultimate cool guy who got to hang out with all the biggest stars. These days, he’s still in the entertainment industry, but he’s toned down the hairdo – thank goodness.

Now, he’s the host of The Voice, which is basically the TRL of singing competitions. He’s also a dad, so he’s probably trading in his clubbing nights for early bedtimes and dad jokes.

Britney Spears, the princess of pop, gave us “…Baby One More Time” and more iconic dance moves than we can count. Back then, she was the epitome of teen pop royalty, with her pigtails and schoolgirl uniform making us all want to break out into song and dance.

But now? Well, she’s still slaying the game, even if she’s traded in the pigtails for a more mature look. She’s a mom of two, a fitness guru, and a queen of Instagram.

Ah, Christina Aguilera, the powerhouse vocalist! Back then, she was the bad girl of pop, with her edgy style and sultry voice making us all feel a little rebellious.

Well, she’s still a queen but with a more sophisticated vibe. She’s a mom, an advocate for body positivity, and has even been a judge on The Voice. And let’s not forget that time she transformed into a blonde bombshell on us – seriously, how does she look so fierce in every hair color?

Kelly Clarkson, the original American Idol, gave us “A Moment Like This” and the ultimate breakup anthem, “Since U Been Gone.” Back then, she was the girl next door with a big voice and even bigger dreams.

Since then, she’s received several Grammy awards, been appointed a judge on The Voice, and even launched her own talk show. Additionally, she’s a mother of two and always maintains a genuine online persona.

Mandy Moore, who made us all swoon in A Walk to Remember, epitomizes the girl next door. She embodied early 2000s adolescent pop culture back then, making us all wish we had her outfits with her crop tops and butterfly clips.

She was one of the show’s main women and is now a mother and even a successful businesswoman in the cosmetics industry. Not to mention when she transitioned from blonde to brunette and killed it. Even though Mandy is an adult, she still embodies the ideal best friend.

Pink, the ultimate rockstar, sang about their desire to “Get the Party Started.” Back then, she was the rebel queen of pop, with her pink hair and bad girl attitude, making us all feel slightly cooler. Nowadays, she’s still a boss but with a more mature edge.

She’s a mom of two, a political activist, and even a Michael Jackson Video Vanguard Award recipient. And let’s not forget that time she performed while suspended from the side of a building – seriously, how does she do it?

Lil’ Kim, the original queen of hip-hop, gave us many iconic fashion moments and some pretty sick rhymes too. Back then, she was the ultimate bad girl of rap, with her colorful wigs and barely-there outfits, making us all feel slightly naughty.

She’s still a legend but with a more refined look. She’s a mom, an activist, and a reality TV star. Lil’ Kim might have grown up, but she’s still the queen bee of hip-hop.

Jennifer Lopez is an awe-inspiring triple threat. Back then, she was the epitome of a pop star, with her abs of steel and hoop earrings, making us all want to hit the dance floor.

JLo is a mom, an actress, a singer, and even a fashion icon. JLo might have evolved, but she’s still that unstoppable force who always knows how to make us dance.

Hilary Duff is one of our childhood Disney Channel queens. Back in the day, she was the sweet girl next door, with her butterfly clips and low-rise jeans, making us all feel slightly cooler.

Hilary is now a mom of three, an actress, and even a pop star. And let’s not forget that time she got a ‘sup?’ tattoo – seriously, how does she make even the most basic tattoo look cute?

The ideal female group, Destiny’s Child, is responsible for “Say My Name” and far too many perfectly synchronized clothes. They were the reigning R&B queens back then, making us all feel like we could take on the world with their powerful attitude and harmonies.

Though they’ve parted ways, they’re still iconic. Beyoncé is a solo superstar and the epitome of multi-tasking, Kelly Rowland is a mother and a judge on The Voice Australia, and Michelle Williams is a Broadway actress and mental health champion.

The pop-rock princess Michelle Branch gave us more angsty lyrics than we could count. She was the queen of the early 2000s, with her guitar and middle part, making us feel like we could start our own band.

She’s a mom of two, a country singer, and even a Grammy winner. And let’s not forget that time she collaborated with Santana – seriously, how does she make that guitar sound like magic? Michelle might have grown up, but she’s still that cool girl who makes us want to pick up a guitar and start singing.

Nelly Furtado is the sassy Canadian pop star who gave us “I’m Like a Bird” and more songs with some pretty catchy hooks. She was the queen of the early 2000s, with her funky style and soulful voice, making us all feel like we were flying.

She’s a mom, a feminist, and still a singer. She likes to switch up her styles and is still active, though not in the traditional limelight like she was in the 2000s.

Shakira, our Colombian queen, taught us that our “Hips Don’t Lie” and was the hottest import in the 2000s. She was the ultimate belly dancer, with her signature blonde hair and sassy attitude, making us all want to learn how to move like her.

She’s a mom, a philanthropist, and even a soccer mom. And she just recently released a hot track that had the world talking about her personal life in a pretty epic way.

Mya gave tons of sultry vocals that made her an R&B queen. With her crop tops and choreography, we all feel like we could be her backup dancers.

Now, she’s a vegan, a health and wellness guru, and an actress. Plus, she won Dancing With the Stars. Seriously, how does she make those moves look so graceful?

Avril Lavigne, the ultimate punk rock princess, gave us more angsty lyrics than we can count. Back then, she was the queen of the early 2000s, with her ties and eyeliner, making us all feel like we could be rebels too.

She’s a Lyme disease survivor, a philanthropist, and a mom. On top of all that, she’s still giving us rocking anthems and having some pretty epic collaborations – like the one she did with Nicki Minaj.

Coming from rock and roll royalty, Kelly Osbourne offered us a glimpse inside her family through The Osbournes and made us all want to dress a bit more punk rock. She ruled the early 2000s back then, inspiring us all to try out new styles, with her purple hair and black eyeliner.

And now? She still has a bossy attitude, but it’s a more sophisticated one. She’s a TV personality, a singer, and a fashion star. And let’s not forget the time she completely changed her look. How did she do it, exactly?

Ashlee Simpson brought us “Pieces of Me” and countless more rock classics. She was Jessica Simpson’s cool younger sister back then, and we all wanted to be her best friend, and we envied her black hair and skater outfits.

She’s now a fashion designer, a mother, and a reality TV judge. Not to mention when she was exposed lip-syncing on SNL. How does she still make us laugh about that?

Jessica Simpson gave us “Irresistible” and countless more moments that will live in infamy. She was the blonde bombshell of the early 2000s, and with her high notes and cowboy boots, she gave us all the impression that we could be country ladies.

She’s not just a best-selling novelist but also a fashion icon and mother. Jessica may have altered her look, but she’s still the girl who can make us feel beautiful and secure.

The ideal boy band, N’SYNC, is responsible for “Bye Bye Bye” and several more perfectly timed dance routines. These guys were maybe the most popular heartthrobs of the early 2000s, and their matching costumes and frosted tips made us all shout like crazed fans.

The boys (men?) are now solo performers, actors, and some even host game shows. They reunited at the famous festival Coachella, and they still looked good.

Backstreet Boys were the ultimate boy band who gave us “Everybody” and more swoon-worthy ballads. They were the dreamy boys of the late ’90s. Their frosted tips and coordinated dance moves made us all fall in love.

They’re still making music, touring the world, and one is even hosting their own cruise. And let’s not forget that time they brought N’SYNC on stage with them. Seriously, did the world stop for a second? Backstreet Boys might have changed their hairstyles, but they’re still those guys who know how to make us feel like we’re living in a dream.

Missy Elliott, one of the most iconic queens, was the funky diva of the early 2000s. Her futuristic outfits and unique sound inspired us all to feel like we could dance like her.

She’s a Grammy-winning artist, a producer, and a mentor to many young talents. Missy Elliott might have changed her style, but she’s still that woman who knows how to make us feel like we’re on top of the world.

Gwen Stefani ruled the ’90s punk scene, making us all aspire to have platinum blonde hair and daring style. She’s a TV personality, a fashion icon, and even a coach on The Voice.

She also reunited with No Doubt, and she could still rock that plaid and get into that punk rock state of mind. Although Gwen Stefani may have undergone a physical transformation, she’s still that cool girl that shows how to be invincible and stand her ground in a man’s world.

Eminem, the king of rap, was the angry young man of the ’90s, with his controversial lyrics and rebellious persona making him a lightning rod for criticism.

He’s a Grammy-winning artist, an actor, and a father. On top of all that, he can still deliver a controversial rhyme that makes us all think about the world.

Brandy, the R&B diva who gave us “The Boy Is Mine,” was the queen of the ’90s soul scene, with her signature braids and sultry vocals making us all want to be like her.

She’s an actress, a mother, and a reality TV star. Plus, she has been a contestant on Dancing With the Stars, like many of our ’90s heroes.

Tara Reid is the actress who gave us American Pie and more than a few cringe-worthy moments. Back then, she was the ‘it’ girl of the early 2000s, with her blonde locks and carefree attitude making her the envy of every party scene.

She’s a reality TV star, a Sharknado survivor, and even a self-proclaimed Instagram influencer. And let’s not forget that time she tried to start a fashion line. Seriously, what was she thinking? Tara Reid might have changed her style, but she still knows how to party – or at least tries to.

Ryan Reynolds is now best known for his sarcastic humor and determination, which is why we even got a big-screen rendition of Deadpool. But back then, he was the fresh-faced heartthrob of the early 2000s, with his charming smile and boyish good looks making him the object of every teenage girl’s affection.

Well, he’s still as handsome as ever but with a more seasoned and confident vibe. He’s a father, husband to Blake Lively, and even a successful entrepreneur and cellphone mogul – though he just sold that company for a pretty penny. Plus, who can forget that time he trolled Hugh Jackman on Twitter? Classic!

Ah, Jewel, the folk singer who stole our hearts with her angelic voice and folksy guitar back in the ’90s. Back then, she was all about the flannel shirts and rustic aesthetic, singing about heartbreak and the simple life.

Jewel still has the voice of an angel but with a little more glam and sophistication. She’s branched into other genres, including country music and acting. And let’s not forget her stint as a judge on The Sing-Off.

The Fresh Prince himself, Will Smith, was all about those colorful outfits, the high-top fade, and some seriously funky beats. He was the king of rap, the Fresh Prince of Bel-Air, and the man we all wanted to be.

He’s gone from rapping to acting, from comedy to drama, and he’s done it all with style and grace. He’s even managed to raise successful kids in the process. Will Smith might not be the Fresh Prince anymore, but he’s still the king of our hearts.

Angelina Jolie has come a long way since her days of battling in ancient tombs in Lara Croft: Tomb Raider. Back then, she was all about those thrilling action scenes, that signature ponytail, and those luscious lips.

She’s traded her weapons in, though, for a director’s chair and her ponytail for a chic bob. Angelina Jolie may not be a Tomb Raider anymore, but she’s still a force to be reckoned with.

Ah, Su-Chin Pak, the former queen of MTV News. Remember when she was on our screens daily, bringing us the latest and greatest music news? Those were the days.

These days, Su-Chin is still working in the media but in a more behind-the-scenes capacity. But don’t worry, she hasn’t lost her cool factor. She’s still got that edgy style and that irreverent sense of humor. Su-Chin Pak may not be reporting on the latest music trends anymore, but she’s still a total rockstar in our eyes.

Sway Calloway, the man, the myth, the legend. Remember when he hosted MTV’s RapFix Live and Total Request Live? He was always the coolest guy in the room, with his smooth voice and effortless style.

Nowadays, Sway is still killing it in the media world, hosting his show on SiriusXM and continuing to be an authority on all things hip-hop. Sway may be a little older now, but he’s still got that same charm and swagger that made us all fall in love with him back in the day.

Quddus, the former host of MTV’s Total Request Live, was a beloved face in the early 2000s. With his charming smile and infectious energy, he made every interview feel like a fun conversation. And let’s not forget his unique name, which sounds like a superhero from a distant land.

Today, Quddus is still as charismatic as ever, and his social media is filled with inspiring posts about mindfulness and wellness. Who knew the guy who introduced us to the Backstreet Boys and Britney Spears would turn out to be such a zen master?

Damien Fahey, the former host of MTV’s TRL, was a staple on our TV screens during the early 2000s. From his spiky hair to his funky wardrobe, he was the epitome of cool. Fast forward to today, and Fahey’s style has definitely evolved.

He’s now sporting a more sophisticated look with a neatly trimmed beard and stylish suits. But one thing hasn’t changed – his wit and charm. Whether he’s hosting a show or cracking jokes on social media, Fahey’s still as entertaining as ever.

La La Anthony, the former VJ of TRL, has come a long way since her hosting days. Back then, she was known for her bubbly personality and killer fashion sense.

But now, she’s a full-blown media mogul, actress, and producer. Her style has evolved, too, from wearing crop tops and cargo pants to rocking designer outfits on the red carpet. It’s safe to say La La has leveled up since her TRL days, and we can’t wait to see what she does next.

Oh, Miley Cyrus! Who could forget her Hannah Montana days? She rocked that blonde wig and sang about the “Best of Both Worlds.” But now, she’s all grown up and twerking her way across stages. She’s even got a few scandals under her belt. But hey, who doesn’t?

Miley is still making music but with a new edge. And let’s not forget her love of animals, tattoos, and tongue-out poses. She’s certainly not afraid to be herself, and we can’t help but love her for it.

Kim Kardashian, the reality TV star turned beauty mogul turned law student, has come a long way since her early days as Paris Hilton’s sidekick. Back then, she was all about low-rise jeans and oversized sunglasses.

But now, she’s all about body positivity, inclusivity, and contouring. Kim’s empire has expanded to include everything from shapewear to mobile games, and she’s always breaking the internet with her bold fashion choices and headline-grabbing relationships. Love or hate her, there’s no denying that Kim K has cemented herself as a pop culture icon.

Benji Madden, the rocker who once dated Paris Hilton, has undergone quite the transformation since his Good Charlotte days. Back then, he was all about the spiky hair and angsty lyrics, but now he’s a family man with a wife – Cameron Diaz – and two kids.

He’s also sporting a sleeker, more refined look, with his tattoos now hidden under sharp suits. Who knew the guy who once sang “Lifestyles of the Rich and Famous” would end up settling down and blending in with the rest of us common folk?

Lauren Conrad, or LC as we knew her from the early days of Laguna Beach, has come a long way since her days of high school drama. From reality TV star to fashion designer, she’s been busy building her empire.

Now, as a mother of two and successful businesswoman, she’s definitely got her hands full. But let’s be real, we’re all still hoping for a Hills reboot where we can see her fabulous fashion and hear her iconic “I want to forgive you, and I want to forget you” line again.

Oh, JT, how we love thee. From boyband and heartthrob to solo artist, actor, and everything in between, Justin Timberlake has been a force in the entertainment industry for decades. Remember those frosted tips? How about that denim suit?

Thankfully, he’s ditched those fashion faux pas and graduated to a more refined style. He’s also gone from “Cry Me a River” to “Can’t Stop the Feeling” and repeatedly proven his versatility. And let’s not forget his acting chops, like his roles in The Social Network and Trolls. Please, keep it coming, JT!

Katy Perry, the colorful pop sensation, has had quite the journey from “I Kissed a Girl” to “Roar,” and beyond. Remember when she rocked blue wigs and cupcake tops? Now she’s a mom, sporting a shorter ‘do and crooning ballads about resilience.

She’s also been a judge on American Idol, which is kind of like if your high school crush suddenly became your teacher. But one thing remains constant, her quirky style and love for everything whimsical. Keep being you, Katy, we wouldn’t want it any other way!

Taylor Swift, the queen of breakup songs, has come a long way from her country music days. Back then, she was all about cowboy boots and guitars, but now she’s more likely to be found strutting around in high heels and a sparkly dress.

Of course, she’s still singing about her love life, but now she’s more likely to be dating Hollywood hunks rather than small-town boys. Regardless of the changes, one thing remains the same – her ability to write catchy tunes that get stuck in your head for days.

Ah, Rihanna! From “Pon de Replay” to “Umbrella,” she’s always been a boss. But let’s talk about her life now. She’s a billionaire now! Talk about a glow-up! Do you know what else has changed? Her music. Rihanna went from “Disturbia” to “Work.”

She’s also taken over the fashion world with Fenty Beauty and Savage X Fenty. Who knew one person could have so many talents? Along with being a fashion mogul, she’s a new mom and has another child on the way. That big reveal at the Super Bowl Halftime Show was amazing!

Mariah Carey, the ultimate queen of Christmas songs, has ruled the music industry since the ’90s. Back then, she rocked the stage with her iconic high-pitched vocals and larger-than-life personality.

Nowadays, she’s still slaying but with a more relaxed and glamorous vibe. She dominates the charts and our hearts with her impressive vocal range and impressive diva attitude. Plus, her holiday tunes are a must-listen every December, making her the unofficial queen of Christmas. It’s safe to say that Mariah Carey is still one of our time’s most influential and talented singers.

Dr. Dre, the man who helped put the West Coast rap scene on the map, has certainly come a long way since his days with N.W.A. Back then, he was rapping about “Straight Outta Compton,” but now he’s more focused on his business ventures and producing for other artists.

With his success in the music industry, he’s also been able to branch out into other areas like film, and even selling headphones. We guess you could say he’s gone from rap artist to corporate mogul – and he’s still making beats that make you wanna bop your head!

Oh boy, Lindsay Lohan! She was the wild child of Hollywood back in the day, always getting into trouble and causing a scene. But hey, that’s just what made her so entertaining, right?

Nowadays, she’s been laying low and focusing on her career, but we still can’t forget those good old days of her partying it up and getting into all sorts of shenanigans. Maybe we’ll see her return and she’ll give us something to discuss again!