25 most popular celebrities of the past 25 years

This story is part of a series to celebrate Yahoo’s 25th birthday. Thanks for joining us along this wild, wonderful ride.

In 1995, TLC’s “Waterfalls” was a huge hit, Toy Story captured kids’ hearts, Seinfeld and Friends were dominating the airwaves, Nicholas Cage won an Oscar for Leaving Las Vegas and Yahoo was born. A lot has changed over the past 25 years — and a lot hasn’t! Check out 25 of the most popular celebrities Yahoo users have followed from reality stars and socialites to actors and rappers.

Nadya Suleman (Octomom)

Nadya Suleman rocketed to tabloid fame — and an infamous moniker, Octomom — after breaking the record for the most live births at once, 8, in 2009. Octomom underwent IVF treatments for all her 14 children, and was implanted with 12 embryos before delivering octuplets, leading to her Beverly Hills fertility doctor to later have his license revoked. Suleman was vilified for being a single mother who relied on food stamps, for reportedly getting plastic surgery to look like her idol Angelina Jolie, for selling photos and stories about her family to magazines like the National Enquirer, and for turning to stripping to earn money. Suleman largely fell out of the spotlight until 2018, when The New York Times declared “the Octomom has proved us all wrong” and detailed her “happy household.” Now, she lives quietly in California, where her kids are said to be vegan, polite, and read two books a week.

Lil Wayne

One of the most successful recording artists of all time, with more than 100 million units shipped worldwide, Dwayne Michael Carter Jr., otherwise known as Lil Wayne, started in the mid-‘90s as a teen member of Southern hip-hop crew the Hot Boys. And while he later battled legal and health issues, his career just got hotter and hotter. In 2012, he became the first male artist to surpass Elvis Presley with the most entries on the Billboard Hot 100 (with 109 songs), and over the course of his quarter-century career, he has won five Grammy Awards, 11 BET Awards, two MTV Video Music Awards, four Billboard Music Awards and eight NAACP Image Awards. His latest achievement? Performing as the Robot on the post-Super Bowl LIV episode of The Masked Singer for a viewing audience of nearly 24 “milli.”

Kate Gosselin

On April 10, 2007, the world was introduced to Kate Gosselin, her husband John and their 8 kids on the Discovery (later TLC) show John and Kate Plus 8. The series followed the big brood — twins Cara and Mady and sextuplets Alexis, Hannah, Aaden, Collin, Leah and Joel — in their hometown of Hershey, Penn., but it was Kate, with her cockatoo-like hairstyle that really captured America’s hearts.

The Kardashian/Jenners

Even before the 2007 premiere of Keeping Up With the Kardashians, Kim Kardashian was plotting her future as a celebrity, proclaiming in a 1994 home video, "When I'm famous..." Both on-and-off camera, the blended brood of siblings — Kim, Khloe, Kourtney, Rob, Kendall and Kylie — along with matriarch Kris Jenner (and ex Caitlyn Jenner) have endured breakups, motherhood and tabloid scandal, while revolutionizing reality TV, body-positivity, selfies and makeup contouring.

Britney Spears

Yahoo was still in its infancy when Spears exploded onto the scene, with her debut 1998 song “...Baby One More Time,” and readers watched as she rocketed to the heights of fame, selling 150 million records worldwide, as of 2017, according to Billboard, and becoming an iconic artist and performer. They were also there for the drama Spears has experienced as she transitioned from sweet bubble gum teenager — she was famously photographed with a landline telephone and a Teletubby for the cover of Rolling Stone in 1999 — to the accomplished mother of two teenage sons. During that time, Spears overcame a bad breakup with fellow teen idol Justin Timberlake; a quickie marriage to childhood friend Jason Alexander; an almost unwatchable show, Britney and Kevin: Chaotic, with second husband Kevin Federline; and, in 2007 and 2008, an infamous breakdown in which she shaved her head and attacked the paparazzi with an umbrella. The “Circus” singer ended up entering into a conservatorship, in which someone is appointed to make her legal and financial decisions, and she remains in one today. All along, her loyal fans have continued to root for the still massively successful music star, who’s looking happy these days.

Kate Winslet

Before Titanic made her a household name and target of intense door-hogging shaming, the British actress had wowed audiences as a homicidal teen in Peter Jackson’s Heavenly Creatures (1994) and lovestruck Marianne Dashwood in Ang Lee’s Sense and Sensibility (1995). The latter film resulted in her first Oscar nod, and after multiple nominations she took home Best Actress for 2008’s The Reader. Her filmography also includes standouts like Eternal Sunshine of the Spotless Mind, Steve Jobs, The Holiday and the domestic drama that reunited her with Leonardo DicCaprio, Revolutionary Road. Along with her Oscar, the Mildred Pierce star is also a Grammy and Emmy winner, making her just one Tony shy of the exclusive EGOT.

Adele

Adele launched her career as a humble, cardigan-sweatered student with 19 (and a Best New Artist Grammy winner in 2009), then matured into the ladylike torch singer that has ruled the Grammys, pretty much every other music awards show, the Guinness Book of World Records, and the charts ever since. Her second studio album of breakup ballads, 21, was certified 14-times platinum in the U.S. alone; its follow-up, 25, sold 22 million units worldwide; and her James Bond theme "Skyfall” even won the Oscar for Best Original Song. The reclusive superstar, now age 31, has been off the scene for a few years, but she just announced that her hugely anticipated fourth album will arrive in September, so expected her to hit even more milestones in 2020 and beyond.

Robert Downey Jr.

How much do we love the Earth’s most popular Avenger? 3000, obviously. Single-handedly starting the Marvel Cinematic Universe in 2008’s Iron Man was a superheroic second-act comeback for RDJ, who spent the first half of his career publicly wrestling with some serious personal demons. Even as he impressed critics and audiences in movies like Less Than Zero and Chaplin, Downey’s hard-partying ways made him tabloid fodder, and led to a string of courtroom appearances and rehab stints in the late ‘90s. Getting fired from Ally McBeal in 2001 after a relapse seemed to be the last straw, but the actor slowly pieced his career back together thanks to career-best work in such films as Kiss Kiss Bang Bang and Zodiac. Downey’s fight to reclaim Hollywood’s trust inspired Iron Man director Jon Favreu to fight for him to be the first and only choice to play Tony Stark… and the rest is comic book movie history.

Usher

His self-titled debut album, released when he was 16 years old and one year before Yahoo’s launch, may have stalled on the charts, but since 1997’s six-times-platinum My Way, the R&B singer dancer, actor, entrepreneur, and former Voice coach has made his way to superstar status. Although the eight-time Grammy-winner, whose full name is Usher Raymond IV, has sold more than 75 million records worldwide and was the top Billboard Hot 100 artist of the aughts decade, his music-industry achievements haven’t been limited to his own recording career. He also played a big part in the discovery and development of another huge 2000s star, Justin Bieber, signing the then-13-year-old YouTube singer to the Raymond-Braun Media Group (RBMG), a joint label venture with Scooter Braun.

Charlie Sheen

Actor Charlie Sheen’s past quarter-century kept people guessing and, at times, gasping. In the late ‘90s alone, the Spin City star was publicly named as a client of Hollywood madam Heidi Fleiss, pleaded no contest to charges that he assaulted a former girlfriend, and narrowly survived a drug overdose. Over the next decade, he had two tumultuous marriages: one to actress Denise Richards that involved a restraining order against him, and one to Brooke Mueller, which led to him entering a guilty plea to a charge of domestic violence. Unsurprisingly, ugly custody battles were part of both splits. Perhaps most infamously of all, in 2011, Sheen ranted against Chuck Lorre, the creator of Two and a Half Men, the hit show where he was earning a higher salary than any other actor on TV. It happened at a time when Sheen was supposed to be in rehab. Instead, he used his time off to bash Lorre and the show in a number of bizarre interviews, during which he coined phrases such as “tiger blood” and “winning” that quickly went mainstream. “I am on a drug. It’s called ‘Charlie Sheen,’” he told ABC News in February 2011. “It’s not available because if you try it once, you will die. Your face will melt off, and your children will weep over your exploded body.” Sheen was eventually fired from Two and a Half Men and replaced with Ashton Kutcher. In November 2015, the saga grew darker, as the Major League star revealed that he was HIV positive. He seemed to be in a much better place by 2019, when he revealed during an appearance on Jay Leno’s Garage, that he’d been sober for a year-and-a-half.

Mariah Carey

Darling, you had to know Mariah would be on this list. By the late ‘90s, she was well on her way to becoming one of the most successful artists of all time, today having sold more than 200 million records. But in the years since, her personal life also drew people to search online. In 1997, she revealed a split from record exec Tommy Mottola, then, in 2001, went on to release the box office flop Glitter and had a bizarre appearance on MTV’s TRL, in which she showed up unexpectedly and stripped off her shirt while handing out ice cream. (She later said the on-air meltdown was the result of exhaustion.) Actor Nick Cannon was the star’s next husband, and she gave birth to their twins — nicknamed ‘dem babies — in 2011. Cannon filed for divorce in 2014, and she’s been in other relationships, but her ex still has her back, whether it’s because Eminem is claiming that he once dated her, she’s weathering an epic lip syncing scandal, as she did in 2017, or they’re giving their children a dream Christmas, complete with live reindeer. Carey has a reputation to uphold, as both a diva and as the Queen of Christmas, thanks to her song, “All I Want for Christmas Is You.”

Pamela Anderson

Whether it's steamy pin-up shots or relationship dramz, the bombshell has grabbed headlines for decades. While her looks initially made her famous (she’s record holder for most Playboy covers), the Baywatch alum further built her brand with acting roles, by authoring books and establishing herself as an activist, from animal rights to Assange. Though through it all, the now 52-year-old’s love life has been a soap opera hard to look away from. Marrying Tommy Lee after four days — their stolen sex tape, his jail sentence, their reunions — down to her recent 12-day marriage with producer Jon Peters. And let's not forget Kid Rock, husband no. 3 and 4 Rick Salomon as well as her scorched earth breakup with Adil Rami in between. Yet she still believes in love, according to her poetry, which often accompanies the still steamy photos she shares of herself. Also in the last two decades , we've watched Anderson’s sons with Lee, Brandon Thomas, 23, and Dylan Jagger, 22, grow up from adorable red carpet accessories to budding stars themselves. Talk about full circle.

Drake

Who would have thought that the kid who started the millennium as an actor on Degrassi: The Next Generation would become the actual voice of a generation and one of hip-hop’s all-time biggest stars? Over the past decade, Aubrey Drake Graham has blazed a trail with his sensitive-rapper persona, racked up 44 Grammy nominations, headlined Coachella (where he got smooched by Madonna), sold more than 170 million records, and charted more songs on the Billboard Hot 100 than any solo artist in recording history. He’s also become one of the interweb’s most ubiquitous and beloved memes, thanks to his awkward dad-dancing in the “Hotline Bling” video, which has racked up 1.5 billion YouTube views.

Jennifer Lawrence

The actress, who broke out in 2010’s Winter’s Bone, skyrocketed to become one of Hollywood’s most sought-after stars of the decade with roles in the X-Men franchise and The Hunger Games trilogy. Esteemed for her work with director David O. Russell, she had audiences captivated with her roles in Silver Linings Playbook (2013), for which she won an Oscar for her performance, as well as American Hustle (2014) and Joy (2016). Lawrence became beloved for her relatable leading lady energy and her friendships with fellow stars like Amy Schumer, Adele and Emma Stone. Her romances with fellow actor Nicolas Hoult, Coldplay frontman Chris Martin and director Darren Aronofsky were splashed across tabloids. Lawrence took a step back from her high-wattage roles and relationships - but stayed in the spotlight nonetheless - marrying Cooke Maroney, an art dealer, in October 2019.

Miley Cyrus

Miley Cyrus was just 2 years old at the time that the Yahoo brand was launched. But in the 25 years since, she’s become one of the world’s most famous celebrities, making enough headlines and causing enough controversy to last multiple lifetimes. From her debut as Hannah Montana on the Disney Channel in 2006, to her upcoming seventh studio album release, the 27-year-old has found her way into the news for who she’s dating, what she’s smoking and the philanthropic causes close to her heart. Not to mention her unforgettable 2013 VMA’s performance, which she said changed her life, her career and culture forever.

Angelina Jolie

The past 25 years have been quite a rollercoaster for the Hollywood wild child now sometimes referred to as “Saint Angelina.” To wit: one Oscar (for 1999’s Girl, Interrupted), a handful of Golden Globes, six children, three marriages (to Jonny Lee Miller, Billy Bob Thornton and Brad Pitt, respectively), four turns as director, a UN global ambassadorship and honorary damehood, one famous dad (Jon Voight), three major franchises (Tomb Raider, Kung Fu Panda, Maleficent) and, yes, countless gossip headlines. Jolie — who’ll be hitting screens this year in Marvel’s The Eternals — is also credited with raising awareness for BRCA gene testing following an op-ed about her own 2013 preventive double mastectomy.

Paris Hilton

The heir to the Hilton fortune, Paris Hilton capitalized on her fortuitous lot in life to become famous for doing ... nothing. After an X-rated tape of the socialite was leaked, she parlayed that popularity into becoming a reality TV star on the hit show The Simple Life alongside Nicole Richie. At 38, Hilton has been a pop culture mainstay for most of her life, capitalizing on her name to not only become notorious but a truly successful businesswoman. In fact, her fragrances have reportedly done $2.5 billion in sales since 2004.

Brad Pitt

Brad Pitt has arguably been the biggest movie star in the world over the last 25 years. Seriously, check out his IMDB page ... crazy, right? Pitt has been in a movie every single year since 1991, although it was a close call in 2018 when we only saw him for a brief flash in Deadpool 2. Back in 1995, Pitt won a Golden Globe for his role in 12 Monkeys and just this year he won an Academy Award for Once Upon a Time… in Hollywood. You can't ask someone, "What's in the box?" without delivering the line like Pitt's character in Se7en and it's impossible to explain a list of rules without the first one being, "You do not talk about it," like in Fight Club. As popular as his movies have been, Pitt's love life has made just as many headlines. After being married to America's "best friend" Jennifer Aniston, Pitt's blockbuster Mr. & Mrs. Smith ushered in the Angelina Jolie years. Pitt is back to being a bachelor, although he and Aniston recently reuniting at the SAG Awards has everyone hoping the two can rekindle their relationship.

Jennifer Aniston

After booking the role of a lifetime in Friends, the actress spent ten seasons as Rachel Green, solidifying her status as America’s favorite girl next door. After a series of relationships, including Jon Stewart, Adam Duritz, Tate Donovan and Paul Rudd, in the ‘90s, Aniston brought in the new millennium by wedding Brad Pitt. In 2004, the iconic sitcom came to an end — and her marriage finished off as well just a year after that. In the past decade and change, she’s starred in movies like We’re the Millers, Cake and Horrible Bosses and recently made her return to TV (ish) with The Morning Show and winning a Golden Globe for her performance.

Oprah

Over the past 25 years, Oprah transformed from a popular talk show host into one of the most influential women in the world. She earned the nickname “Queen of All Media” because of her phenomenally successful show, which regularly examined issues particularly affecting female viewers couldn’t find elsewhere before ending in 2011, as well as for having her very own magazine (O began in 2000) and the ability to send a book to the top of the New York Times bestseller list with the creation of Oprah’s Book Club in 1996. And then, she went and started her own network, OWN. She also made headlines along the way for her appearance in the iconic 1997 episode of Ellen DeGeneres’s sitcom, Ellen, in which DeGeneres’s character came out as gay; her fight with beef producers following an episode of her show on Mad Cow Disease; her establishment of a school for girls in South Africa; her influential endorsement of Barack Obama in the 2008 election; her friendship with CBS This Morning anchor Gayle King; and acting roles in movies such as A Wrinkle in Time. By September 2019, she had to shut down fans clamoring for her to run for office herself.

Shania Twain

The same year that Yahoo debuted, the crossover country-pop crush dropped her second album, The Woman in Me, which sold 20 million copies worldwide. Its follow-up,1997’s Come on Over, was even bigger, selling nearly 40 million copies and yielding a whopping dozen singles, including the iconic anthem "Man! I Feel Like a Woman!" Though she taken various hiatuses over the years due for personal and health reason, the five-time Grammy-winner is still the one for many fans (Post Malone among them), holding the record as the 10th best-selling recording artist of all time and reaching new audiences with her Vegas residency and recent sizzling Billboard Music Awards performance.

Leonardo DiCaprio

A Slate article recently riled up DiCaprians when it cast doubt on the actor’s movie star credentials pre-Titanic (1997), and for good reason. By the time he played doomed ship passenger Jack, the former child star had already established himself as an Oscar nominee (for What’s Eating Gilbert Grape), teen mag pin-up and the most crushable Shakespearean hero of all time (Baz Luhrmann’s Romeo + Juliet). Since then, the now-45-year-old star has finally nabbed that Oscar (for 2015’s The Revenant), become Martin Scorsese’s go-to guy, emerged as an environmental activist and, most recently, starred in Quentin Tarantino’s award-winning Once Upon a Time ... in Hollywood.

Tom Hanks

Here’s one way to kick off the quarter-century: On March 27, 1995, the Philadelphia and Forrest Gump star won his second Best Actor Oscar in a row, a feat that hadn’t been pulled off since Spencer Tracy in 1938, nor since. In addition to being billed as the most likable guy in Hollywood, Hanks has used his everyman appeal to woo Meg Ryan over email (You’ve Got Mail), befriend a volleyball as a bearded survivalist (Castaway), rescue a World War II soldier (Saving Private Ryan), slip on Fred Rogers’s cardigan (A Beautiful Day in the Neighborhood) and, most crucially, come to terms with an arrogant space hero while leading a ragtag team of toys (the Toy Story series).

Eminem

Marshall Mathers exploded onto the scene in 1999 with The Slim Shady LP and has been one of the biggest hip hop stars in the world ever since. With Dr. Dre by his side, the white kid from Detroit took over a hip hop world that had been previously dominated by East Coast and West Coast rappers. After Marshall introduced the world to his alter ego, Slim Shady, he followed up with The Marshall Mathers LP and The Eminem Show, both certified Diamond by the RIAA. The controversial rapper known for his violent and homophobic lyrics, shocked everyone with a show-stopping performance of "Stan" with LGBTQ icon Elton John at the 43rd Grammy Awards. Marshall surprised people again in 2002 when he hit the big screen, starring in 8 Mile. The next year, Eminem won an Academy Award for Best Original Song for "Lose Yourself," making him the first hip hop artist to ever win an Oscar. 17 years later, Eminem is still shocking the world. In January, Marshall surprised everyone with the release of his 11th studio album, Music to Be Murder By, and in February he surprised the Academy Awards audience with a performance of "Lose Yourself." So it seems like the Marshall Mathers show won't be ending any time soon.

Beyonce

It was in 1996, one year after Yahoo’s launch, that Beyoncé’s group Girl’s Tyme changed its name to Destiny’s Child. And Bey met her destiny indeed, absolutely dominating pop culture for the next quarter-century. After Destiny’s Child became one of the best-selling girl groups of all time, Beyoncé embarked on a quintuple-threat solo career, highlights of which included the most Grammys nominations for a female artist; the viral “Single Ladies” dance; groundbreaking surprise visual albums, Beyoncé and Lemonade, that literally changed the album-release-cycle game; iconic performances at “Beychella,” President Barack Obama’s inauguration, and three Super Bowls; and a dazzling pregnancy announcement that became the most-liked photo in Instagram history. And it seems like Beyoncé is just getting started.