Top 20 Coolest People of the 90s

If you were a ‘90s kid, you had to love Robin Williams. The beloved late comedian could make us both laugh and cry in so many of his roles, whether they were live-action or animated. His mix of energy and emotional intelligence helped make films like “Aladdin”, “Jumanji”, and “Mrs. Doubtfire” unforgettable. His more dramatic performances were also exceptional, and he received a well-deserved Oscar for “Good Will Hunting”, playing Matt Damon’s warm-hearted therapist. What ultimately made Williams so cool was his commitment, no matter the assignment. He could be starring in a movie, giving an acceptance speech, or simply doing an interview, and he would always give it his all!

Few people can be said to truly “ooze charisma”, but Antonio Banderas absolutely does. In the ‘90s, the Spanish actor rose to the spotlight for American audiences with roles in movies like "Philadelphia", "Desperado", and "Interview with the Vampire”. By the time “The Mask of Zorro” was released, he was a bonafide Hollywood movie star. As New York Times film critic Janet Maslin put it, Alejandro Murrieta was “the role that Antonio Banderas was obviously born to play.” Not only is Banderas incredibly handsome and charismatic, but he also has a great sense of humor about himself. What’s cooler than someone who doesn’t take themselves too seriously?

We thought Ryder was so cool in the ‘90s—and we still do! This is one celebrity who just exudes coolness! Her unpredictable clothing choices—whether leather jackets, blazers, or band tees — showed us that fashion is about more than high-class heels and expensive jewelry. Her roles in movies like “Edward Scissorhands” and “Little Women” didn’t give audiences a choice; we all fell under her spell of coolness before we knew what hit us! According to Rolling Stone magazine, Ben Stiller has been quoted saying “It’s funny—girls really like her, and guys really like her. Every guy I’ve ever talked to has a crush on her.” Years later, not much has changed. With her work in “Stranger Things”, the crushes and admiration only continue!

We still have plenty of cool action stars, but few come close to Arnold Schwarzenegger in the ‘90s. The Austrian bodybuilder-turned-actor had our blood pumping throughout all of his action films! “The Terminator” franchise sequel, “Conan”, “Total Recall”, and “Eraser” always manage to keep us on our toes with Schwarzenegger’s impressive performances. His comedies, like "Kindergarten Cop" and "Junior", are equally brilliant. While there were a few misses, like his rather campy performance as Mr. Freeze in “Batman & Robin”, Schwarzenegger’s charisma has always remained as big as his muscles. Film critic Roger Ebert credited Schwarzenegger's humility, sense of humor, and sensitivity, among other qualities, for his rise to fame. The muscles are cool, but the later-governor of California was even cooler!

#16: Keanu Reeves

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Honesty time! How many of us have fantasized about being Neo or Johnny Utah? Keanu Reeves, in the ‘90s (and beyond), exuded a kind of coolness that suggests he’s not bothered by anyone or anything. Perhaps that’s not surprising, given that his name is Hawaiian for “cool breeze over the mountains”. But the beloved Reeves always finds a nice balance. He doesn’t act like he’s superior to anyone or unwilling to be a little silly. He’s a natural comedic talent, as seen in the “Bill & Ted” films, and has received plenty of adoration from his co-stars and directors, including Gus Van Sant, who praised Reeves' mix of charisma, good looks, and innocence. We have one word for Keanu Reeves and his coolness: “Whoa.”

If you wore a yellow plaid blazer in the 1990s, you were probably influenced by fashion-conscious Cher Horowitz in the classic teen comedy "Clueless". Although Alicia Silverstone had made her debut in “The Crush”, her best-known role to this day is Cher. Her director, Amy Heckerling, compared her to Marilyn Monroe in terms of appeal. Although her intentions can sometimes backfire, Cher shows true growth over the course of the film and helps the people around her in the process. In an interview for the film's 25th anniversary with Vogue, Silverstone talked about the effort she made to reveal Cher's heart beyond her materialism. Her performance shows it’s nice to be important, but it’s more important to be nice.

#14: The Rock

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Before he was movie star Dwayne Johnson, he was the renowned professional wrestler The Rock. Even before he was acting in films, his presence in the ring during the ‘90s was so palpable that he was already a star in the eyes of millions of wrestling fans. Debuting in the WWF (now the WWE) as "Rocky Maivia" in 1996, he turned heel and adopted "The Rock" name and persona, leading to feuds with the likes of "Stone Cold" Steve Austin and Triple H. But this was one bad guy audiences could root for: his charisma and catchphrases turned him into a sensation! Incredible as both an athlete and an entertainer, Dwayne “The Rock” Johnson truly...well, rocks!

Turn on the radio today, and you can hear Janet Jackson. You might not always hear her songs, necessarily, but you can definitely hear her influence on modern artists like Lady Gaga, Beyoncé, and Ariana Grande. Either way, albums like “Janet” and “The Velvet Rope” sound as fresh now as they did almost 30 years ago! She wasn’t content to be simply known as “Michael Jackson’s younger sister”, so Janet consistently pushed herself as an artist, and even dabbled in acting, landing herself a starring role in John Singleton's "Poetic Justice". Trying to measure Janet Jackson’s impact on the entertainment industry is like trying to measure the impact of the sun on the Earth: it’s simply too great to do!

The Beastie Boys came together in the early ‘80s, a time when hip-hop certainly wasn’t as fully mainstream. As the genre further exploded in popularity throughout the ‘90s, the New York trio became anything but a footnote, releasing multiple number-one albums! The coolest thing about the group wasn’t even their prodigious skills on the mic, mixing board, or musical instruments. It was how they were always willing to learn, whether that meant incorporating new styles into their sound or making amends for previous offensive lyrical content. The death of Adam "MCA" Yauch in 2012 brought about the end of the group, but they'll always be true hip-hop legends.

#11: Will Smith

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No one forgets when they first set eyes on Will Smith. We were all amazed by just how much effortless charm he exhibited. Seriously, does this guy drink a magical charisma smoothie for breakfast? After establishing himself as a musical talent with DJ Jazzy Jeff & The Fresh Prince, the path to superstardom was further paved by his hit sitcom, “The Fresh Prince of Bel-Air”. He went on to star in movies like “Six Degrees of Separation” and "Bad Boys". But, it was the film “Independence Day” that saw him both fighting off some unfriendly extraterrestrials and earning himself a permanent spot on the celebrity A-list. Even as his star power grew, Smith remained relatable, and his movies’ billion-dollar earnings speak for themselves.

What do you call someone who tops the Billboard, box office, and New York Times Bestseller charts all in the same decade? You call her “Madonna”. The pop icon furthered her cultural dominance in the ‘90s by releasing number one singles like “Vogue”, and “Take a Bow”, and appearing in films like “A League of Their Own” and “Evita”, the latter of which earned her a Golden Globe. While not all of her ventures were well-received, such as her leaning into a more provocative image with the release of her book titled “Sex” and her more explicit stage shows, she always kept our attention. And, she ended the decade with one of her very best albums, the adventurous “Ray of Light”.

#9: The Notorious B.I.G.

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Whether you know him as Christopher Wallace, Notorious B.I.G., Biggie Smalls, or Biggie, there's no question that he's one of the greatest minds that hip-hop has ever known. Brooklyn-born-and-bred, Biggie rose to fame with his album, "Ready to Die", and songs like "Juicy" helped turbo-charge New York's image as a hip-hop powerhouse. He even collaborated with Michael Jackson! Multiple publications have named Biggie as the greatest rapper of all time; and, in 2020, he was inducted in the Rock and Roll Hall of Fame. Tragically, his life was cut short in 1997 after being killed in a drive-by shooting. Although he’s no longer with us, Wallace’s legacy lives on through his massive influence.

#8: Tony Hawk

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If you can only name one skateboarder, it’s probably Tony Hawk. Although he was already an accomplished skateboarder as a teenager in the ‘80s, the ‘90s were when Hawk's fame truly began to soar. Competing in the X Games, performing patented tricks like the "900", and launching his own line of video games, made Hawk a hero for every kid at the skatepark hoping to achieve their own dreams of vert skateboarding stardom. In an interview with The New Yorker, Hawk said that he never imagined any future for himself besides skateboarding. If you’ve seen what he can do with a skateboard, you’ll know he means that.

Even in an ensemble as talented and revered as the “Friends” cast, Jennifer Aniston stood out. Our ‘90s selves still want to go shopping with Rachel Green! Aniston not only did an amazing job at making Rachel likeable, she also managed to make her someone other struggling twenty-somethings could relate to. Many aspired to look like her, too, with the "Rachel" haircut becoming a popular ‘90s 'do. She also inspired fashion trends, such as plaid skirts and overalls. Aniston, of course, had great chemistry with her fellow cast members, most prominently with David Schwimmer as her on-again, off-again partner, Ross. She also starred in numerous ‘90s movies, and later continued a strong career in both TV and film.

#6: “Stone Cold” Steve Austin

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The Rock was definitely one of the coolest wrestlers of the ‘90s but, at the risk of being called “jabronis”, we have to give the number-one spot in that category to his rival, “Stone Cold” Steve Austin. A central attraction of the WWF's "Attitude Era", Austin contributed to a major spike in pro wrestling's popularity. He thrilled fans with wrestling feuds, including those with Bret Hart and chairman Vince McMahon. Plus, we can’t forget about the stunts Austin pulled, like driving a Zamboni up to the ring and tackling his boss! He also popularized an amazing finishing move better known as the “Stone Cold Stunner”. If there’s anyone who knows how to stun, it’s Steve Austin.

Denzel Washington won his first Oscar in 1989 for “Glory,” but took his talent to an even greater level in the ‘90s. The movie and theater star had one of the best runs of any actor of the decade. You’ll remember him excelling in biopics like "Malcolm X” and "The Hurricane”, and thrillers like "The Pelican Brief" and “Devil in a Blue Dress”. Part of Washington’s success as an actor comes from his commitment to his roles. As his “Malcolm X” costar Angela Bassett told The New York Times, “When Denzel has to go to work, he goes to work." Whether on stage or on the screen, you can always count on Washington to deliver.

In the ‘90s, Naomi Campbell put the “super” in “supermodel”. The British fashion icon was a star of runways, magazines, music videos, and more. As a member of the "Big Six" of supermodels, including Kate Moss, Campbell broke barriers for models of color and ruled fashion shows with her striking looks and poses. She was the first Black model to appear on the cover of French Vogue and the first Black model to grace the cover of the September issue of American Vogue. Her ambition spread to other ventures, including making music, appearing in movies, publishing books, and releasing her own line of fragrances. Famously outspoken about issues like racism in the fashion industry, Campbell changed modeling as we know it for good.

The end of Kendrick Lamar’s album “To Pimp a Butterfly” features an imagined conversation between him and Tupac Shakur. The message is clear: Lamar hopes to be as great as one of his idols: the man most synonymous with West Coast hip-hop. Shakur positively shook up the industry with his music, which ranged from boastful to conscious, and was a key participant in the harsh feud between the West and East Coast hip hop scenes. But, you didn't need to get swept up in any drama to hear the talent on display. He was also an acclaimed and influential actor, appearing in films like “Poetic Justice” and “Above the Rim”. Shakur was tragically killed in 1996, but he will always be known as a legend.

In the ‘90s, ‘23’ became something more than a number. In fact, just about anything associated with Michael Jordan automatically became cooler, including basketball itself. As a member of the six-time championship-winning Chicago Bulls and the 1992 Olympics "Dream Team”, Jordan embodied the word “dedication”. If you’ve seen “The Last Dance”, you’ll know what we mean when we fawn over just how much of an icon Jordan was, not only as an athlete, but also as a personality. Oh, and let’s not forget he also gave us the iconic “Space Jam” movie! His influence was indisputable. To this day, kids are still out on the court, aspiring to make slam dunks in their own Air Jordans!

Coolness is earned by resisting conformity and standing proudly in your own power. When Kurt Cobain and his bandmates in Nirvana rocketed to fame in the early ‘90s, they defied the notion that mainstream rock music had to be devoid of meaning or feeling. Nirvana's intense music helped millions of music fans feel as though they were finally being heard. Songs like “Smells Like Teen Spirit” and “Heart-Shaped Box” are as catchy as they are cathartic. Cobain died in 1994, only a year after the release of the band’s final album, “In Utero”, but his, and Nirvana’s, lasting cultural impact makes them the coolest of the ‘90s.