When you’re dressing for a very public event, you want to make sure you look eye-catching. For celebrities, drawing attention is a part of the gig. These stars definitely knew how to draw the camera’s attention. As awards season rolled around, these stars wore their weirdest and wildest outfits to different music award shows.
Madonna — 1990 VMAs
In 1990, when Madonna attended the VMAs, she rocked a look that no one really saw coming from the pop queen at the time. It’s one few could forget.
When Madonna came on stage to perform “Vogue”, the singer had chosen one of the wildest ensembles of the night that better resembled the French Revolution than the ’90s pop scene. Like many performances, Madonna and her coordinated dancers somehow pulled the look off.
Pamela Anderson — 1999 VMAs
Pamela Anderson is well-versed in catching the camera’s eye when she hits the red carpet. The 1999 VMAs were no different.
One of her wildest looks from the awards show season relied on a variety of textures and patterns that definitely falls under the “maximalist” approach to fashion. The star wore sequined, patterned pants paired with a white corset and — perhaps the real focal point — an oversized, pink, fluffy hat.
Jennifer Lopez — 2000 Grammys
Awards shows are a great chance to show off the best designer looks on the red carpet. Jennifer Lopez really changed things with this green dress. The star wore the plunging green dress to the 200 Grammys.
If the executive chairman of Google Eric Schmidt is to be believed, we can even thank this dress in part for the existence of Google Images. As for J.Lo herself, she said, “It was a nice dress. I had no idea it was going to become such a big deal.”
Pink — 2000 VMAs
Pink has long been noted for her distinct style. Back in 2000, at the VMAs, she went for a colorful look that we’re still talking about more than 20 years later.
The star went for an eye-catching hairstyle that lived up to their name and from there, it was all gold and denim. In real early 2000s fashion, she opted for a crop top and a pair of jeans — with the waistband cut off, of course.
Toni Braxton — 2001 Grammys
There are some dresses that are ultimately rather simple but they still stand out for years to follow their appearance. That’s what happened with this 2001 Toni Braxton dress.
Attending the Grammys, the singer wore a long white gown designed by Richard Tyler that left little to the imagination. When asked about the iconic dress, Braxton told US Magazine, “I’ve always gone a little risque with all my other awards [show outfits]. I decided that before I got married and had babies, I’d wear this.”
Macy Gray — 2001 VMAs
Musicians release new albums much to their fan’s delight all the time. However, the ways they might announce them might be different.
Macy Gray fans following the 2001 VMAs had the chance to see the release date of her then-new album — and all thanks to the dress she wore! The front read “My new album drops Sept. 18th, 2001” while the back demanded fans to “Buy it!” Who could say no to that order?
Britney Spears and Justin Timberlake — 2001 AMAs
Sometimes, our favorite celebrities can take current trends and really make them larger than life. Everyone loved denim in the early 2000s, right?
Still, one of the wildest and most unforgettable outfits is hands-down Justin Timberlake and Britney Spears’ matching ensemble — which they wore to the 2001 AMAs. A full-length denim gown alongside a denim suit with a matching Stetson is a look that no one forgot.
Britney Spears — 2001 VMAs
Of course, you don’t become an icon like Britney Spears on one outfit alone. She’d attend the VMAs that same year with an iconic accessory.
Stepping on stage to perform her song “Slave 4 U”. The outfit was already a great look for Spears but what really made it memorable was the giant snake draped across her shoulders for the duration of the performance! It seems like this is an accessory that would take a lot of upper body strength.
Jonathan Arndt — 2004 CMAs
This snapshot of Martina McBride and Jonathan Arndt really shows how he went with the wildest options in his wardrobe to attend the 2004 CMAs.
The outfit here is made up of pastels but the colors are only part of what makes it so shocking. The brocade jacket and fur collar really tie it all together to shock everyone seeing it. Plus, with all the jewelry and props, who could forget this look?
Eddie Montgomery — 2005 CMAs
Still, we’re not so sure that Big Kenny had the wildest outfit at the 2005 CMAs. It seems like Eddie Montgomery was ready to give him a run for his money. At an awards show where we’ve seen a lot of jeans and suits, this outfit definitely takes the cake.
The long, embroidered coat already stands out for its silhouette but the musical notes, roses, and especially the bold letters reading “Broadway” across the front of the jacket undeniably make a statement.
OK Go — 2007 Grammys
The band OK Go definitely made a visual splash at the 2007 Grammys with some of the wildest outfits of the night. The band kept their faces covered with red fabric and donned matching body suits of red and gold brocade.
They were detailed, just like a regular suit, but also included a hood and matching accessories. One band member later said, “We’re dressed in the future — the future dressed us. This is actually us in an hour.”
Lady Gaga — 2009 VMAs
If there’s one musician that’s known for rocking some of the wildest outfits that Hollywood has seen, it’s Lady Gaga. She didn’t disappoint at the 2009 VMAs. The star started out in what seemed like a rather tame white outfit.
That was until she took to the stage to perform her song “Paparazzi”. In a real moment of music meets performance art, Gaga committed to an intense number that left her stumbling on stage soaked in fake blood to finish the song off.
Nicki Minaj — 2010 AMAs
Nicki Minaj has sported some wild looks over the years. However, the outfit she wore to the 2010 VMAs might just be one of the wildest to date.
The coral-colored dress wouldn’t stand out too much on its own but Minaj knew exactly what details it needed. Who could look away from a dress with a golden exoskeleton like this? It definitely made for an unforgettable outfit.
Lady Gaga — 2010 Grammys
One of the outfits that Gaga debuted on her 2010 trip to the Grammys was this purple number that looks like it came straight from the future.
The dress was made by designer Armani Privé and it even came with a sharp accessory. Lady Gaga actually wore this dress before she performed at the show for the very first time. It’s not a bad look for a debut at such a massive awards show!
Lady Gaga — 2011 Grammys
If you really want an outfit to stand out, you might want something really wild about it to draw people’s attention. Alone, the neutral outfit that Gaga wore isn’t too shocking.
The shocking part was how she entered the event. Photographers waiting on the red carpet were greeted with a giant egg carried by a group of people, not the singer. Well, actually, she was just inside the egg, waiting for her chance to emerge. Did you know that she was actually in the egg for about 72 hours?!
Nicki Minaj — 2011 VMAs
To make an outfit the wildest one at an awards show, you really have to think outside of the box. What can you do that hasn’t been done before? Nicki Minaj definitely got wild with this silhouette and these fabric choices.
Her upper half is decked out in geometric patterns while the bottom half seems to take inspiration from some more comfortable clothes. Of course, you can’t leave home without your stuffed accessories either.
Grace Jones — 1983 VMAs
If there’s one thing that model, singer, and actress Grace Jones knows how to do, it’s to draw attention when she walks into a room.
At the 1983 VMAs, she brought her signature Avant-garde approach to fashion with this look. The most eye-catching thing about this look — aside from the space-age outline of the outfit — is the ultra-wide hat brim. Rick James even stopped to pose under it at one point!
Katy Perry – 2011 VMAs
Forthe 2011 VMAs, Katy Perry went for a very geometric look. While Katy’s no stranger to eccentric outfits, this one was definitely surprising. The dress and top are fun but aren’t too shocking on their own.
What really made this look stand out was the choice of headwear for the look. We all know the right hat can bring a look together but we probably wouldn’t have thought of this accessory.
Miley Cyrus — 2013 VMAs
After her years at Disney ended, Miley Cyrus really started to take her looks up a notch at awards shows. Some of them have been really shocking!
The bejeweled outfit that she wore at the start of the show was great but didn’t necessarily stand out as weird or wild. That came later when she took to the stage in a bear leotard to perform “We Can’t Stop”. Of course, the giant dancing bears helped with the overall weirdness factor.
Frankie Grande — 2014 AMAs
Ariana Grande has stolen the show at many musical events. At the 2014 AMAs, though, it was brother Frankie Grande that stood out.
This is one outfit that really highlights that sometimes it’s what you don’t wear that will make you stand out. It doesn’t take an eagle eye to see that Grande opted for a painted-on shirt. Like many others on YouTube at the time, Grande didn’t skip out on the neon hair either.
Katy Perry and Riff Raff — 2014 VMAs
Earlier, we took a look at Justin Timberlake and Britney Spears’ iconic matching denim outfits in the early 2000s. It seems like they weren’t the only ones who wanted to rock it either.
For the 2014 VMAs, Katy Perry and Riff Raff decided to pay homage to the famous red carpet look. All in all, they recreated it rather well. It’s definitely reworked for their particular styles, though.
Miley Cyrus — 2015 VMAs
Of course, Miley Cyrus wasn’t going to get on this list for only one of her VMA looks. She pulled out another creative option for the 2015 VMAs.
She showed up decked out in a pink latex dress complete with balloon accessories reading “Do It” across the front — a nod to one of Cyrus’ own songs. Of course, she needed the perfect hair accessories and with so much pink, it seemed a pig bow was appropriate.
Baddie Winkle — 2016 VMAs
Who says that you have to stop donning your wildest looks as you age? That’s one myth that it seems that Baddie Winkle has been determined to make.
At the 2016 VMAs, she showed up in a body suit reminiscent of the look Britney Spears wore for part of her music video for “Toxic”. Naturally, Baddie Winkle wasn’t about to skip out on her accessories either. Even her cane is bedazzled to match the look!
CeeLo Green — 2017 Grammys
CeeLo Green is no stranger to attending awards shows. So, it makes sense that he knew just how to stand out when he donned this look.
The star showed up to the 2017 Grammys in an outfit that was impossible to miss. He wore gold from head to toe, complete with gold gloves and a gold helmet, so nothing but gold was showing. The memorable look definitely got fans talking.
Cardi B — 2019 Grammys
Cardi B looked her best in this dress that really brings to mind Botecelli’s Venus emerging from the sea. There’s more than just a silhouette here, though.
The dress was made by Mugler and it has no shortage of pearls and silk to pull the look together. She even has a tower of pearls in her hair! She was dressed to impress — and that she did. In fact, later that night, she became the first woman to win the Grammy for Best Rap Album.
Sophie Turner — 2019 Billboard Music Awards
Sophie Turner skipped the usual gown for a bodysuit at the 2019 Billboard Music Awards. The look was bold and it definitely caught people’s eyes.
The getup brought a variety of opinions from critics but a few things made the outfit stand out. For one, the pattern of the silver bodysuit stood out. The silhouette also stood out, thanks to the sharp shoulders hanging a little lower than shoulder pads would.
Billy Porter — 2020 Grammys
Billy Porter knows exactly how to stop the paparazzi with his red carpet looks. The American Horror Story alum had one of his wildest looks for the 2020 Grammys.
For this look, Porter was head to toe in sequins, adding silver tassels on his hat and pants legs. The fringe on the hat was more than just decorative, though. At Porter’s command — or his stylist’s — the fringe opened to reveal the actor’s face.
The Weeknd — 2020 VMAs
There are some looks at the VMAs that really stand out for the effects that go with them. The suit The Weeknd wore to the 2020 VMAs wasn’t too shocking.
His makeup, on the other hand, caught people’s eyes. After all, it was a pretty realistic rendering of what he might look like after a fight. The look ended up being promotional for his new video and he’d don it again a few more times the next year.
Doja Cat — 2021 VMAs
Doja Cat has often challenged expectations when it comes to fashion. This look really is no different but it surprised many viewers. In 2021, the singer attended the VMAs in this number.
Well, she wore a few different outfits throughout the night but this one was by far the most memorable. She donned this getup onstage while accepting a VMA award, admitting that “I look like a worm. That’s done. I never thought I’d be dressed as a worm while accepting an award.”
Machine Gun Kelly — 2022 AMAs
More than once, Machine Gun Kelly has made headlines for some outrageous outfits at various events. This one really turned some heads, though.
A purple suit really isn’t that shocking at the AMAs. In 2022, Machine Gun Kelly wore this purple suit to the AMAs and it’s easy to see why it stood out. If nothing else, it would definitely keep people from getting into your personal space.
Lizzo – 2023 Grammys
Lizzo has skyrocketed to fame and it’s easy to see why! The star makes great music and has a charming personality that draws fans in. She made an impression in florals at the 2023 Grammys.
The singer had a two-layered look. The base of the look is an orange gown that’s gorgeous in its own right. However, it was the cloak of roses that really made this outfit as memorable as possible.
Harry Styles — 2023 Grammys
There are some stars that need no introduction. At this point, it seems like Harry Styles definitely qualifies as one of these superstars.
The star opted for a multi-colored jumpsuit. It could almost look like a patchwork pattern if all the pieces weren’t given a sequined effect to make sure this wild look still catches the light.
Alisha Gaddis — 2023 Grammys
Lizzo wasn’t the only one to bring florals to the red carpet at the 2023 Grammys. It was a trend Alisha Gaddis decided to play into as well. Still, the two gowns have a lot of differences.
Compared to Lizzo’s more monochromatic look, this colorful piece gives us a variety of flowers. It’s a gown that almost brings to mind Florence Pugh’s flower-covered look in Midsommar.
Sam Smith — 2023 Grammys
Sam Smith stood out on the red carpet at the 2023 Grammys but they were ready with an entire ensemble look with a few other stars.
In all, they showed up with Kim Petras, Violet Chacki, Gottmik, and more. They led the crew in a red cloak and gloves, complete with a cane and top hat. If that wasn’t interesting enough, the top hat featured a veil too.
Shania Twain — 2023 Grammys
There are some stars who just know how to get the camera’s attention. Shania Twain definitely did that for the 2023 Grammys.
The singer went for a head-to-toe cow print look. With a massive printed hat and bell-bottom pants, we literally mean from head to toe. Now, would it really be a glam red carpet look if those cow spots weren’t sequined?
Blac Chyna — 2023 Grammys
Blac Chyna knows how to work the spotlight but even this look was surprising to many fans. Who could have expected it? The short dress brings to mind images of the Black Swan.
Of course, it seems like Blac Chyna took things to the extreme. Wouldn’t it be pretty hard to do ballet in an outfit like this? One thing is for certain — this dress had no shortage of different textures to experiment with.
Dencia — 2023 Grammys
Dencia had another iconic look to bring to the 2023 Grammys. It seems like everyone really brought out their best at this event! Dencia’s look was almost the classic black gown.
Instead of a plunging neckline like J.Lo, though, she opted for a high collar encrusted with blue and green jewels. If you look closely, her dress also has black jewels nestled into the fabric as well. The cobra-like dress really captured everyone’s attention as she made her way across the red carpet.
Lucky Daye — 2023 Grammys
If you want to wear a black suit to the Grammys, you have to think a bit outside of the box if you want to stand out. Lucky Daye accomplished that. To start, it’s not just a black suit.
To catch the lights, there are sequins all over the outfit to make it shine. What really sets it apart, though, is the melting metallic piece to the puzzle that honestly looks a little hard to move around in.
Lil’ Kim — 2002 Grammys
Lil’ Kim owned the 2002 Grammy Awards with a bold moto-vibe in her red Chanel leather getup. Complete with a “CC” helmet, low-rise pants, and a cropped leather jacket, she showcased her fearless fashion sense.
Mixing high fashion with biker elements at such a high-profile event highlighted Lil’ Kim’s groundbreaking style, making a lasting impact on the red carpet and cementing her status as a trendsetting icon.
Missy Elliot — 1999 Grammys
Unsurprisingly, the iconic Missy Elliott turned heads when she showed up to the 1999 Grammy Awards in this bold white jacket and hat combo. You may be thinking — there’s nothing better than a classic white suit.
Well, that is unless you’ve got some feathers to complete the look! It may be unconventional, but we honestly love the look. Let’s bring feathers back! Who’s with us?
Avril Lavigne — 2003 Grammys
From her iconic anthems to rebellious ways, this punk queen had every millennial in the early 2000s — boys and girls — swooning. Naturally, Lavigne arrived at the 2003 Grammy Awards with a message to share with her fans… and the world.
Unlike the glitz and glam that most female celebs endure before a red carpet appearance, Lavigne decided to skip all of that and rocked on! We love her for it.
Alicia Keys — 2002 Grammys
Alicia Keys made a bold fashion statement at the 2002 Grammy Awards, opting for a memorable ensemble that blended elegance with urban cool. She turned heads in a see-through veil paired with a white tank top, jeans, and a pair of sandals — seamlessly merging sophistication and street style.
Not only is she one of the most talented singers of our generation, but she’s also a total style icon. Don’t believe us? Check out her collection with Athleta activewear. You can thank us later!
Lil Nas X — 2020 Grammys
Lil Nas X rocked the 2020 Grammy Awards in a sharp pink suit with a matching hat, turning heads and showing off his signature style. The hot pink ensemble effortlessly blended boldness with sophistication, proving that the “Old Town Road” sensation knows how to make a statement on the red carpet.
Lil Nas X’s choice of a standout outfit showcased his individuality and fashion-forward approach, marking the event as yet another moment where he stood out in both music and style.
Billy Dean — 2003 CMAs
The CMAs aren’t often known for having some of the wildest outfits of the awards season, as you might expect at the Grammys or VMAs. Still, that doesn’t mean that there aren’t any outfits to write home about.
In 2003, Billy Dean took to the carpet in an embroidered suit that no one was going to forget anytime soon. The back featured an embroidered American flag and the rest was decorated with stars and eagles. Very patriotic!
Jeff Bates — 2003 CMAs
It seems like Billy Dean wasn’t the only one interested in embroidered jackets when the CMAs rolled around in 2003. Jeff Bates jumped on the bandwagon too, although the design he opted for wasn’t quite as patriotic.
Instead, it was an eclectic mix of skulls, vines, roses, dice, cards, and more. From the looks of it, this jacket was definitely an eye-catcher. This is one trend that it seems like everyone loved at the 2003 CMAs.
Big Kenny — 2005 CMAs
In 2005, the CMAs hosted some eccentric looks and outfits. Take a look at this photo, for instance, which features Big Kenny and John Rich.
We could spend some time on John Rich’s two-toned denim but it’s Big Kenny’s outfit that sticks out to us more. It seems almost as likely that he’s going to step on stage to give us a production of Les Miserables as he is to accept an award.
Kenny and Christiev Alphin — 2009 CMAs
When you’re coming to an awards show as a couple, it opens up a lot of opportunities to come up with the wildest outfit you can think of together.
Just the suit and dress that Kenny and Christiev Alphin chose for their red-carpet look wouldn’t have stood out too much. No, what really makes these 2009 CMAs look stand out so much is the matching top hats that really made this so memorable.
Dillon Francis — 2022 Grammys
Usually, when you hit the red carpet, you want to look your best. For most stars, this means breaking out the mind-bogglingly expensive suits and gowns.
Dillon Francis thought well outside of the box and showed up in something no one was expecting when the 2022 Grammys rolled around. After all, not many people walk the red carpet in jeans and a t-shirt, carrying the snacks they bought from Walgreens on the way.
By Simon Saunders –
We’ve gotten used to seeing these famous faces constantly, but we don’t often look back to what they were like at the start of their career. Thanks to the internet, though, we can see these A-listers hanging out with their younger selves. Let’s take a look at where they started and how far they’ve come with these awesome pics!
Dwayne “The Rock” Johnson
Although nowadays he’s known as one of the most wholesome and busiest actors in Hollywood (just take a look at how many movies he’s starring in the next year), he didn’t start out as part of the glitz and glam of Tinseltown.
Known by his stage name, “Rocky Maivia” (a combination of his father’s and grandfather’s wrestling names), Johnson began wrestling in 1996. He was critical to the creation and success of the World Wrestling Federation, aka WWF. Although his acting has taken center stage, he does still compete.
Mary-Kate and Ashley Olson
Everyone that grew up in the ‘90s and early 2000s learned of Mary-Kate and Ashley when they began playing the adorable Michelle Tanner in Full House. From there, their resumes only got more impressive with time.
Their last role as part of their acting empire, however, was in New York Minute in 2004. Since then, they’ve left the acting world but not the world of glamor — they’ve created a lucrative fashion brand and now spend their time managing it.
James Van Der Beek
Seeing Dawson Leery next to James Van Der Beek is making us remember exactly why we had a huge crush on him back when Dawson’s Creek was airing in 1998, and James was 19.
It also totally shows us why we still love him. Just look at that charming smirk! Of course, he’s still acting; his latest roles include Matt Bromley in Pose and Grant in the comedy horror film Bad Hair.
Beyoncé
It was clear very early on that Beyoncé was going to be a star — from a young age, she participated in (and won) several singing and dancing competitions. Her more serious break came when the singing group she had joined, Girl’s Tyme, morphed into Destiny’s Child.
From there, we all know Beyoncé’s meteoric rise to fame. After all, who can forget such hits as “Survivor”, “Bootylicious”, and”Crazy in Love” (which was also her first number-one single)? Do we really need to explain how Queen Bey is still proving what an immense talent she is to this day?
Haley Joel Osment
Haley Joel Osment was probably the cutest child star of the ‘90s. He first got attention at the age of four when a talent scout signed him and got him in commercials. His first major appearances on the silver screen were as a young Forrest Gump, and, more importantly, as Cole in The Sixth Sense.
From there, the huge roles just kept coming. While his projects since hitting his late teens have slightly dwindled, Osment is still acting both on TV and in films. He’s also been the voice behind the beloved Sora in the Kingdom Hearts video game franchise.
Cher
Cherilyn Srakisian’s journey toward becoming the Goddess of Pop began with a cute little number called “I Got You Babe” — which shot Sonny & Cher straight into fame. At the same time, she also established herself as an impressive solo act.
Cher has since become an incredible musical icon, conquering every stage and every entertainment industry she could think of. Even after over 60 years of making music, this powerhouse doesn’t seem to be slowing down.
Paula Abdul
She might be known nowadays as a talented choreographer, actress, singer, and dancer (and as one of the iconic original judges on American Idol), but Paula Abdul actually began her career as a cheerleader for the Los Angeles Lakers.
Interestingly, the Jacksons saw her cheering and gave her a chance to choreograph several music videos for them. From there, she slowly transitioned into creating her own music. Her career since then has been filled with music and dance.
Ralph Macchio
Wax on, wax off — polish your eyes and take a look at the original Karate Kid, Ralph Macchio. Macchio began professionally acting at age 16, with his first role being Jeremy Andretti in Eight Is Enough.
Of course, his major break came when he played underdog Daniel in The Karate Kid, a role he has reprised many times over the years — including, most recently, in the sequel series Cobra Kai.
Madonna
At the young age of 20, Madonna dropped out of college and moved to New York City with $35 in her pocket to try to make it big as a modern dancer. For quite a few years, she picked up odd jobs while pursuing her career in music.
In 1982, she released several singles that garnered enough attention to propel her forward, all the way to “Like a Virgin” and “Material Girl” stardom. The rest, as they say, is history. The Queen of Pop continues to make headlines and albums to this day.
Dolly Parton
It’s impossible not to fall in love with the sweet smile and immense talent that is Dolly Parton. Before becoming a worldwide sensation, though, Dolly was just a humble songwriter for others. She finally became known for her singing talent with the debut of her first album, Hello, I’m Dolly.
After winning the hearts of every country music lover out there, Dolly branched out to other genres, also becoming a pop sensation. Her latest work includes a rock album, which she started working on after getting nominated for induction into the Rock and Roll Hall of Fame.
Kate Moss
Beautiful British model Kate Moss began her career in 1988 when she was just 14. She was spotted by Sarah Doukas at the airport in New York after returning from a holiday in the Bahamas. Moss became known for her “grunge” look.
Beyond becoming a renowned model over the years, Moss has also gone into fashion design, creating several collections with Topshop. In 2016, she founded her own agency, KMA (Kate Moss Agency), signing on Rita Ora and Esmé Creed-Miles, among others, as clients.
Leonardo DiCaprio
Looking at a young Leonardo DiCaprio sure takes us back. He first began appearing in commercials at age 14, soon gaining his first role in The Outsiders. We do, of course, have to mention the incredible star status he gained as a teen heartthrob in the late ‘90s with Romeo + Julietand the massive success of Titanic.
From there, it’s been a pretty steady rise for Leo, as he’s still a huge star. Even so, nowadays, it seems like people are more concerned with his dramatic love life than with his up-and-coming films.
Elton John
With his Farewell Yellow Brick Road tour underway, what a time to talk about the incredible career of the amazingly talented and iconic Elton John. John began performing at age 15 at a local pub.
His real career, however, began when he met his longtime musical partner, Bernie Taupin, in 1967. The duo has since created the musical talent that is Elton John together. Of course, it’s impossible to sum up his decades-long career, so, let’s just say that it’s still going strong.
Lionel Richie
He’s once… twice… three times a massively talented singer! It’s Lionel Richie, everyone! And can we just say that this Motown wonder has aged so well? This is one handsome 70-something-year-old that we’d love to be serenaded by.
After all, he was one of the most successful balladeers of the ‘80s — and for good reason. His solo career might have begun in 1982 with his album Lionel Richie, but those sweet dulcet vocals are still going strong today.
Tom Hanks
While we might most fondly think of Tom Hanks (beyond his wholesome self) as a serious dramatic actor, he actually got a start with a series of comedy films that got some pretty good reviews.
While Splash and Big did wonders for his career, his true shot to stardom came with the iconic Forrest Gump. Hanks has since only reached higher with his many amazing films and truly unforgettable roles.
Richard Gere
Although he began his career with a starring role on Days of Heaven, Richard Gere rose to prominence thanks to American Gigolo. This transformed him into one of Hollywood’s favorite heartthrobs.
That’s probably why he got his role in Pretty Woman. He also found himself playing the suave Billy Flynn in Chicago. He’s still acting while also working on his musical talent.
Robbie Williams
Can we just take a moment to swoon over 16-year-old Robbie Williams in his early Take That days? Unfortunately, the young star had quite a few difficulties with illicit substances during those days, and he left the group in 1995.
Lucky for us, he kept making his own music and even made his return to the group in 2006. He has received 18 Brit Awards, alongside tons of other music awards worldwide — he definitely does Take the Crown.
Matt LeBlanc
How you doin’, Matt LeBlanc? ‘Cause you’re looking like you’re doing just fine! He may be older and somewhat rounder these days, but we’re definitely hoping that today’s Matt is a lot wiser than his younger character of Joey Tribbiani.
While Joey might be his most known character, LeBlanc’s career actually started quite a few years before his Friends fame. In fact, his first appearance was in a Heinz Ketchup commercial way back in 1987. Of course, he’s still acting, although he hasn’t yet found a TV role since his show Man With a Plan was canceled in 2020.
Britney Spears
By now, we all know what an incredible struggle and journey Britney Spears has undergone in order to gain back her independence and return to the industry… on her terms. So, we really couldn’t care less that she doesn’t look 20 anymore.
The 41-year-old singer has been spending her time working on her book and on her family with Sam Asghari. We can only hope, however, to soon hear that ‘Oops!… She did it again’ and returned to making music.
Clint Eastwood
He might have been the man with no name in Sergio Leone’s Dollars Trilogy, but we definitely know Clint Eastwood’s name. This Spaghetti Westerns veteran has, since his time in the Wild West, also graduated to directing many films.
Apparently, his dating history is just as action-filled as his films. Over the years, he’s been connected to many women, eventually fathering at least eight children with six different women. He refuses to confirm exactly how many children he has.
Bruce Springsteen
Thanks to great musicians like Frank Sinatra, Elvis Presley, and the Beatles, Bruce Springsteen became interested in creating his own music at a young age. He got his first guitar in 1964 and soon after joined a band and started performing.
From there, it was nearly a decade of playing with different bands, honing his skills and musical taste. In 1972, he formed a new band, which eventually became the E Street Band. The band still plays with Springsteen to this day.
Emma Watson
Who would have thought that the perfectionist and loyal Gryffindor would grow up to be the fierce and impressive Emma Watson? Okay, yeah, basically everyone. Clearly, Hermione Granger was made to be played by Watson.
Although she hasn’t acted as much in recent years (with the notable exceptions of Beauty and the Beast and Greta Gerwig’s Little Women), Emma is just as outspoken, nowadays taking her activism into board meetings instead of the red carpet.
Mel Gibson
This international star was often compared to the likes of Steve McQueen, Clark Gable, and Humphrey Bogart in his early years, and we can totally see why. Although his citizenship only included the US and Ireland, thanks to a move in his teen years to Australia, that was where he began his career.
His initial movies (like the Mad Max films), cemented Mel Gibson as an action star. However, as he built his skill, people soon learned that he had a talent in other genres as well. In recent years, due to certain statements made by the actor, he hasn’t been as much in the limelight.
Harrison Ford
When it comes to movie roles, Harrison Ford certainly has a type (and we absolutely love it) — a wise-cracking, heart-of-gold criminal. Because how else do you explain the fact that Indiana Jones and Han Solo are so much alike?! Seriously, it took us a moment to recognize which one he was dressed up as in this pic.
Beyond his acting career, which is still thriving (with Indiana Jones 5 out this year), Ford also has quite a few other interests. This includes a pilot’s license, which he’s even used to help the local authorities in Wyoming with a rescue! Now, that’s a true action hero!
Jerry Seinfeld
Like many comedians, Jerry Seinfeld began his career appearing in open-mic nights at different improv clubs. Only, he got really lucky when in 1976, he appeared in an open mic at Catch a Rising Star — which led to him appearing on a televised comedy special!
After becoming a late show favorite guest, Jerry finally created Seinfeld in 1988 alongside Larry David. Amazingly, for a show about nothing, it quickly became the most-watched sitcom on TV and Jerry has been a household name ever since.
Will Smith
Everybody, put your hands together for the one, the only Fresh Prince! But before we saw him on The Fresh Prince of Bel-Air, Smith was using the same nickname to create his musical career as an MC and rapper.
He’s since proven that beyond musical and comedic talent, Will Smith could also move us to tears or make us hold our breath in anticipation in his more action-oriented films. Unfortunately, due to his televised slap, his career seems to have been put on a bit of a hold recently.
Sylvester Stallone
“Yo, Adrian!” shouts Rocky Balboa, but we want to give a shout-out to the great actor behind the hit franchise — Sylvester Stallone! Under the stage name Mike Stallone, Sylvester began his career in 1969. He changed his stage name again just a year later, finally going back to his real name only a few years into his career.
Did you know that his first starring role was actually in a soft adult film? This was obviously before the success of Rocky when he was strapped for cash. Of course, nowadays, he’s far from destitute and is enjoying his hard-earned career success.
Tom Selleck
Say hello to this glorious mustache. The young Tom Selleck definitely stole our hearts in 1980 when he starred as the clever private eye in Magnum, P.I.But, his career didn’t stop there.
He’s been winning us over again and again. Since 2010, he’s been doing so as the head of a family of police officers in the long-running Blue Bloods. In recent years he’s also begun singing — appearing on Nicolas King’s album Act One.
Phil Collins
We “Can’t Stop Loving You”, Phil Collins! From the moment he began sharing his musical talent with the world, we were hooked. Genesis was his big break, but did you know that he actually had a bit of an acting career before getting into music? That clearly didn’t take.
Of course, many of us in the younger generations first got to know him through his incredible work on the Tarzan soundtrack (which he also recorded himself in several other languages). You’ll always be in our hearts, Phil!
Jennifer Aniston
She’s made such a name for herself over the years that it’s hard to consider her a nepo baby, but Jennifer Aniston actually is the daughter of two actors. Of course, over the course of her amazing career, she’s created her own legacy.
Her big break, as we all know, came as Rachel Green in Friendswhen she inspired a generation of young women. She’s since only grown, honing her dramatic acting chops alongside her comedic timing.
Lady Gaga
Mother Monster is in the house! With this pic, it’s basically impossible to tell which is the younger version of Lady Gaga. In any case, we know for a fact that the bullies who used to tell Stefani Joanne Angelia Germanotta that she’ll never be famous have been eating their words for years.
Lady Gaga isn’t just an incredibly talented musician and singer (though she most definitely is that); she’s proven in recent years that she’s just as great at acting. She now moves back and forth between her two passions, and we can’t wait to see her blend them in the new Joker film.
Christina Applegate
Let’s come clean — we all had a crush on Christina Applegate as Kelly Bundy on Married… With Children. There was just something about the beautiful and ditzy character, played by this talented actress, that had us hooked.
Applegate has only gotten better since, taking on more complex roles that really showcase her incredible talent. Seriously, her latest role in Dead to Me is absolutely incredible! Sadly, due to her diagnosis of MS, it looks like she’ll be putting her acting career on pause.
Henry Winkler
His father might have sold wood, but the “only wood” Henry Winkler “was interested in was Hollywood,” according to the cheeky comedian and actor. He began his career straight out of the Yale School of Drama as a stage actor.
His breakthrough came when he got the role of Fonzie on Happy Days. Apparently, he was told he got the job on his birthday! While “The Fonz” might be timeless, younger audiences probably know him better from his roles on Arrested Development or Barry.
Steven Spielberg
You might be tempted to think that Steven Spielberg’s glorious career began with the masterpiece Jaws in 1975, but he actually spent years before that trying to break into the world of directing.
Of course, nowadays, he’s known for his genius directing, having been responsible for some of the most enjoyable and profitable films of all time. His most personal work, semi-autobiographical The Fabelmans, recently hit theaters to rave reviews.
Johnny Depp
Johnny Depp actually began his rise to fame as a musician when he left school at 16 to pursue his rock dreams. It was only at 20, after meeting Nicolas Cage, that he decided to give acting a shot. He became a teen heartthrob when he landed his first big role on 21 Jump Street.
However, he didn’t love the commercial aspect of the role and sought more independent and interesting projects. His role in Edward Scissorhands began a lifelong collaboration with Tim Burton, which is still going strong.
Robert De Niro
Robert De Niro worked in Hollywood for a decade in all sorts of small roles before he got his big break in 1973, when he played a mobster in Martin Scorsese’s Mean Streets. His nuanced acting was apparently perfect for criminal roles, as he was soon cast as Vito Corleone in The Godfather Part II.
Thanks to his many collaborations with Scorsese, De Niro rose quickly from there, marked as an impressively diverse actor. He might not be super handsome, but there’s quite a bit of charm in every character that De Niro plays.
Courteney Cox
Did you know that before beginning her illustrious acting career, Courteney Cox actually worked for the video game company Bethesda Softworks? Well, soon after that, she began acting in all sorts of projects. She finally landed her breakout role in Friends.
While we definitely associate her with Monica Geller, Cox was also recognized at the time as one of the biggest horror actresses with her role in the Scream franchise. Of course, she’s still acting, even returning to set to film the sixth Scream film recently.
Rob Lowe
We might think of him nowadays as the suave and funny aged actor that he is, but Rob Lowe was actually technically a child actor, beginning his career at age 12. His breakout role was in Francis Ford Coppola’s The Outsiders.
He later gained even more fame as Sam Seaborn on the fan-favorite The West Wing. Lowe’s career has only risen to new heights since, and we have to say, he’s just as crush-worthy now as he was in his younger years.
George Clooney
Mr. Silver Fox himself, George Clooney, has only gotten better with age — although he’s always been a heartthrob. His career first began in 1978 when he played an extra on Centennial. But, it wasn’t until 1994 that he landed his first real break in ER.
During his time on the show, he also began appearing in films — showcasing his versatility by starring in comedy, action, and romantic movies. He’s still enjoying that same diversity of roles nowadays as he jumps from project to project, leaving his foxy mark on all of them.
Paul McCartney
Paul McCartney met John Lennon when he was only 15 years old, and was soon invited to join his band, the Quarrymen. They quickly invited McCartney’s school friend George Harrison to also play with them, and soon after, they became The Beatles.
Look, we’re not going to get into Beatlemania, but McCartney was right in the thick of it. Of course, after the band broke up, McCartney created his own solo career, where he’s done extremely well for himself to this day.
Julia Roberts
Then and now, it doesn’t matter — Julia Roberts will forever be our Pretty Woman. But she’s not just an incredibly beautiful person; she’s also an amazingly talented actress that has made us laugh and cry many times over the years.
With Mystic Pizza, Steel Magnolias, and Pretty Woman, Roberts quickly established herself as an A-list leading lady, and she’s kept up that level of success since. She keeps appearing in endlessly diverse roles that make us fall in love with her over and over again.
Drew Barrymore
Let’s take a look at one of our favorite child-actors-turned-acting-adults ever — the fabulous and charming Drew Barrymore. Her breakout role was, of course, as Gertie in E.T. the Extra-Terrestrial. Due to her fame, though, her teenhood was quite complicated.
However, she managed to make it out the other side with her career fairly intact as she became a favorite rom-com and chick-flick actress. Her latest venture has been her talk show, which has quickly become a wholesome must-watch.
Brad Pitt
Brad Pitt tried to make it big in Hollywood for quite a few years before he was finally noticed when he played a supporting role in Thelma & Louise. He then really broke out thanks to his role as Paul Maclean in A River Runs Through It.
It was finally Interview With the Vampire that truly cemented his place in Hollywood. He’s since had an incredibly diverse career thanks to his talent for making each of his characters unique.
Cyndi Lauper
Cyndi Lauper began writing and playing songs when she was just 12, thanks to a guitar that was given to her by her sister. This girl definitely wanted more than just to have fun — in her early singing days with the band Blue Angel, she refused any contract that wouldn’t include the band.
She’s since, “Time After Time”, made us dance with her amazing songs. But, she isn’t just a musical sensation. Did you know that she also acts on occasion, even having a recurring role as a psychic on Bones?
Rick Astley
We’re “Never Gonna Give You Up”, Rick Astley! After all, how could we ever let down the internet’s favorite memeable musician? His most famous song was also his debut solo song, and it shot him to the top of the charts.
Amazingly, Astley decided to retire from music in 1994 to raise his daughter. He returned only in the late 2000s but has since slowly risen back to fame. Of course, he’s become an inescapable part of pop culture in recent years thanks to Rickrolling.
