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Old-School Cool Celebrities Who Still Rock Our World

By Jo Marshall
Share to PinterestOld-School Cool Celebrities Who Still Rock Our World

Old-school cool goes far beyond a hip attitude or widespread fame when singling out those celebrities who fit the bill. True icons have much more to offer the world than a pretty face or a funny dialogue. These celebrities have openly shared their gifts with us all and taken their place as legends within their industries. They grab our attention in ways that spark our curiosity, inspire our imaginations, and encourage us to find our place in the world.


Robin Williams

No matter what role he played, whether it was a desperate father disguising himself as a housekeeper in Mrs. Doubtfire, a somewhat spastic, animated blue genie/life coach in Aladdin, or a mentally unstable photo developer and stalker, Robin Williams took each portrayal to places only he was capable of. While it was his comedy that first stole our hearts, he could also immerse himself into scarier or more dramatic characters that reminded us just how versatile he was. He frequently reminded the public through his movies and stand-up comedy performances, his interactions with fans, and thousands of interviews that we should be kinder to one another. The fact that he named his daughter Zelda, after everyone's favorite princess, made us love him even more.


Carrie Fisher

Born to two of the most famous people in Hollywood, Carrie Fisher was the daughter of singer and actress Debbie Reynolds and actor, singer, and infamous philanderer Eddie Fisher. Carrie was 19 years old in 1997 when George Lucas offered her the role of Princess Leia Organa in a swashbuckling, sci-fi adventure. We loved her from the first moment she appeared in that grainy hologram, with her now-iconic plea: "Help me, Obi-Wan Kenobi, you're my only hope." Fisher's final Star Wars appearance occurred three years after her death through the magic of visual effects in The Rise of Skywalker. Instead of CGI, unused footage from The Force Awakens provided the world a chance to officially say goodbye to the iconic Leia.


Marilyn Monroe

She was not only a symbol for fashion and beauty, but she was also one of the most significant icons in movie history. Monroe's vulnerability and charisma on screen were ever-present, yet, it was her private life that became a source for constant scrutiny by Hollywood gossips and fans alike. Few people know that Marilyn was an intellectual who read constantly when not on set. And, she was a feminist, long before there was an organized movement to back her. When Twentieth Century Fox continuously overworked her and forced her into "dumb blonde" roles, she broke her contract with them and opened her own production company.


Frank Zappa

In the 1960s, the American rock group, Mothers of Invention was performing and experimenting with music like no other band of the time. Their leader was Frank Zappa, a charismatic musical genius who pushed the boundaries of cultural constraints to their maximum limits and shocked society's ears. While his peers were experimenting with hallucinogens and other drugs, Zappa never did. Humor was at the core of his lyrics, but explicit sexuality wasn't uncommon. In the 1980s, his hit song "Valley Girl" introduced the world to the life of a San Fernando Valley schoolgirl and their uh, like, totally, unique way of speaking.


R.J. MacReady and crew

Horror fans around the world claim The Thing is one of the most iconic films ever made. This 1982 sci-fi thriller directed by John Carpenter opened to negative reviews, but years later, critics and movie hounds alike discovered its magic, dubbing it "Alien On Ice." The movie's main character, R.J. MacReady, is a helicopter pilot stationed at U.S. Outpost 31, a research station in Antarctica. His crew encounters a parasitic extraterrestrial, and the adventure begins. Throughout the movie, MacReady/Russell enchants audiences with a constant stream of memetic quotes, which has firmly cemented him among other cultural icons of the movie industry.


Salma Hayek

It was after seeing the movie Willy Wonka & the Chocolate Factory in her native Mexico that Salma Hayek decided she wanted to be an actress. In 1991, she made her way to Los Angeles, and by 1995, director Robert Rodriguez offered her the role of Valentina in the cult favorite, Desperado. She easily matched the intensity and physicality of her co-star, Antonio Banderas, and audiences fell in love. Hayek went on to star in other cult classics like From Dusk Till Dawn, Dogma, and Frida. Although her beauty is unquestionable, her old-school cool status comes from her both her comedic and dramatic acting skills as well as her high-level performances in action roles. Her most recent venture as Ajak in Marvel Studio's Eternals is proof of her ongoing iconic status.


Joaquin and River Phoenix

There's something about acting families that grabs the public's attention, especially if the actors are young and on the fast track to stardom. River Phoenix had a huge future ahead of him, with promises of superstardom lighting his life path. His first major role was in Stand By Me in 1986. By 1988, at the age of 18, he earned an Academy Award nomination for Best Supporting Actor for Running on Empty. But, tragically, with fame comes temptations, and River overdosed on cocaine and heroin, dying at the age of 23. His younger brother, Joaquin, a fervent animal rights activist, also started acting at a young age, starring in several major films, including an unforgettable and award-winning performance in Joker in 2019.


Dick Clark

When teenagers wanted to hear the latest top 40 hits and enjoy some really groovy dance moves from the late 1950s into the mid-2000s, they watched the television show American Bandstand. Its host, Dick Clark, took the show from a local Philadelphia broadcast to a national one, and it didn't take long for audiences to start tuning in. Clark became a go-to authority on music and its industry behind the scenes. Music historians say Clark helped America become more receptive to rock 'n roll, a genre that had previously been the target of criticism from parents, politicians, and religious leaders alike. Race was no barrier on the show from the very beginning. White and Black alike people shared the dance floor, and popular R&B and soul artists performed on the show.


Jimi Hendrix

Influential and creative, Jimi Hendrix opened the world to vast new possibilities that could be achieved through the electric guitar. But that wasn't the only thing that earned him his legendary cool status. He also had a renowned sense of style. Between 1965 and 1970, Hendrix immersed himself in fashions of the time, a cross between Romantic and Victorian aesthetics that rockers around the world were soon emulating. A black hat and belled sleeves became staples in his wardrobe. He honored his Cherokee ancestry by dressing in beaded, fringed, indigenous-style suede fashions for his performances. It was in the summer of 1969 that he performed his famous rendition of the "The Star-Spangled Banner" at the Woodstock Music & Art Fair, a performance that still ranks among the highest in the history of rock' n roll.


Cindy Crawford

Although she may not have landed the cover of the swimsuit edition of Sports Illustrated these days, Cindy Crawford is still one of the most famous supermodels of all time. Her athletic build stood out from the other rail-thin models strutting the runways in the 1980s and 1990s, which led to her multi-million dollar endorsements from some of the biggest brand names in the world, including Revlon and Pepsi. Her success was an early sign of change and a move toward acceptance for the vast range of women's body shapes. Now in her 50s, she's still rocking Instagram with gorgeous photos that remind us what the word "supermodel" really means.


Malcolm and Angus Young, AC/DC

AC/DC, co-founded in 1973 by brothers Malcolm and Angus Young, sold over 110 million albums. Critics and fans alike revere the legendary heavy-metal band for its intense loyalty to fans, musical prowess, and high-energy, theatrical performances. Angus' schoolboy short-trousers outfit, Malcolm's inspired rhythm guitar performances, and their collaborative genius fueled the aspirations of headbangers around the world to be in a band.


Stephen and Jane Hawking

They seemed like an unlikely couple. Stephen Hawking would become one of the most brilliant intellectuals on the planet, an atheist who didn't believe in heaven. His betrothed, Jane Wilde, was a steadfast Christian who had a passion for languages and literature. They married in 1965. Over the next 30 years, they would have three children. Jane would be Stephen's primary caretaker, simultaneously running the household and earning a doctorate in medieval Spanish literature. But with Stephen's growing success came throngs of people entering their lives, including a new nurse with whom he fell in love. The Hawkings separated in 1990 and divorced in 1995.


Patrick Stewart

The road to becoming an illustrious Starfleet captain on the infamous U.S.S. Enterprise can be a long and winding one. Patrick Stewart knew he wanted to be an actor from the age of 12, earning a spot in the Royal Shakespeare Company in the mid-1960s. Then, 25 years later, he became Captain Jean-Luc Picard, a role he played on television and in movies over the next 40 years. Stewart earned even more nerd cred with his role as Professor Charles Xavier in the X-Men film series.


Arnold Schwarzenegger

From world champion bodybuilder to movie star to governor of California, Arnold Schwarzenegger has had a varied career and managed to maintain an infectious demeanor of optimism and tenacity that has attracted a whole new generation of fans. He emigrated to America shortly after winning the Mr. Universe title at the age of 20, then won a dozen more bodybuilding titles after his arrival. As an actor, Schwarzenegger was particularly suited to play action roles with a humorous, slightly snarky twist, which generated some of the most iconic lines in movie history, including "I'll be back" from Terminator and "It's not a tumor" from Kindergarten Cop.


Mick Jagger and Keith Richards

Mick Jagger, lead singer of the Rolling Stones, along with his longtime bandmate, guitarist Keith Richards, have been playing music together for nearly 60 years, although they've been friends for 70. When it came to sex, drugs, and rock ‘n roll, they made their marks on the world together. The two have had their share of spats, throwing out snarky remarks toward each other through the years. But they still love playing together and plan on celebrating their 60-year anniversary on-stage in 2022.


Joe Strummer, the Clash

Guitarist, singer, and songwriter Joe Strummer and his band, the Clash, inspired a generation both musically and politically from the late 1970s to the early 1980s. Though the band only had five years together, they harnessed a unique mesh of reggae, punk, and world-beat rhythms, and intense, three-chord bursts. Their lyrics focused on racial unity and the end of political oppression, but it was Strummer's extreme mohawk that became a visual symbol of the punk rock movement.


Nick Castle

When it comes to the infamous "Halloween" movies, many horror fans relate that it was the first one, released in 1978, that got them hooked on the genre. Nick Castle, a childhood friend of the film's director, John Carpenter, was the first actor to play the part of Michael Myers. Carpenter talked Castle into playing the role, paying him $25 per day.


Sly and the Family Stone

The epitome of cool, Sly and the Family Stone debuted their unique rock, soul, and R&B sound with the 1968 release of their song, "Dance to the Music." The seven-member band was the first racially integrated American band featuring both male and female members. Their songs, including "If You Want Me to Stay," and "It's a Family Affair,'' influenced performers for decades and have generated millions of views on YouTube.


Norman Rockwell

In 1915, Norman Rockwell submitted his first drawings to the Saturday Evening Post. He would end up creating more than 300 covers for the magazine over 47 years, painting optimistic, realistic depictions of what he believed was the American Dream. To this day, he is one of the most recognizable artists in history.


Debbie Harry

There's no question that the charismatic lead singer and frontwoman of Blondie is an old-school cool icon. Her bleached white hair and unique, fashionable outfits are just part of what made her such a fascinating performer. Debbie Harry is — and always has been — fearless. She earned her punk rock stripes in the mid-to-late 1970s in an infamous New York City bar, CBGB, the birthplace of the male-dominated punk rock scene.


Jeff Ament, Layne Staley, Chris Cornell, Matt Dillion, Cameron Crowe

In 1992, Cameron Crowe made a movie called "Singles" that took place in Seattle. The cast included popular and rising stars of the time — Matt Dillion, Bridget Fonda, Campbell Scott, and Kyra Sedgwick, to name a few. The movie hit a chord for movie-goers, but the soundtrack got a lot of attention. It featured music from Pearl Jam, Alice in Chains, Soundgarden, and other top bands of the time. Ament, Staley, and Cornell, three of the founders of grunge music in Seattle, were among those who visited the set.


John Cleese

Though they'd been performing on the BBC since 1969, Monty Python's Flying Circus didn't show up on American televisions until 1974. Monty Python was a surreal comedy group, starring John Cleese, Eric Idol, Graham Chapman, Terry Gilliam, Terry Jones, and Michael Palin. The ensemble poked fun at the upper classes, the absurdity of life, and even a dead parrot. One of the most popular sketches was the Ministry of Silly Walks, featuring John Cleese.


Kurt Russell

Kurt Russell is one of those actors who you just can't help but love. Whether you adore him for classic roles like Snake Plissken or more modern characters like Ego, Russell brings a unique and dynamic charisma to every project he's in. He, like his father, had a baseball career. In the early ‘70s, Russell played for teams like the Bend Rainbows and Walla Walla Islanders before ultimately landing on his father's team, the Portland Mavericks. Were it not for a rotator cuff injury that ended his baseball career, Russell may have never returned to acting and we would have missed out on all his legendary performances.


Brigitte Bardot

Famous for her sex kitten persona, Brigitte Bardot starred in racy European films and her liberated lifestyle was the stuff of legend in the 1950s and 60s. Unfortunately, in recent decades, the French government has fined her six different times for inciting racial hatred and abuse. In 2018, she, along with other prominent French women, published a letter condemning the #MeToo movement.


Harrison Ford

Harrison's fans can't imagine any other actor playing Han Solo or Indiana Jones. But those roles almost didn't happen for him. George Lucas and Steven Spielberg thought Tom Selleck would make an ideal Indiana Jones. Selleck turned it down because he was doing the TV show, "Magnum P.I." Ford also competed against Kurt Russell for the role of Solo, but he eventually won out.


Colonel Sanders

Sure, he can fry chicken, but can he sing? Well, probably not, but Colonel Sanders did love music. In 1968, he released a vinyl LP, Tijuana Picnic because he loved Latin jazz. His thoughts and feelings accompany each song on the album jacket. Sanders also released Christmas albums three consecutive years, from 1967 to 1969, complete with handpicked yuletide tunes performed by a variety of musical artists and television personalities.


Teresa Graves

The star of the 1970s hit show, "Get Christie Love," spawned a famous tagline: "You're under arrest, sugar." Teresa Graves was the first black actress to star in a television drama, ironically, a show about the first black policewoman hired by a big-city police department. Her TV career began as a regular on Rowan & Martin's Laugh-in in the late 1960s, earning fans through her humor, smarts, and super fashionable appearance. She starred in several films, including the comedy-horror, "Old Dracula," opposite David Niven in 1974.


Leonardo DiCaprio, Johnny Depp, Brad Pitt

Oh, to be young, rich, and enjoying major stardom in the 1990s. For fans, the thought of Leonardo DiCaprio, Johnny Depp, and Brad Pitt hanging out together is just too much to imagine. Although Depp's days of hanging out with the other two seemed to have ended with that night, DiCaprio and Pitt have been friends for decades. Both got their start on the same television show, "Growing Pains," though on different seasons, so they never shared any episodes.


Cheech Marin and Elvira

In the 1970s, the stoner-hippie comedic duo Cheech Marin and Tommy Chong were enjoying their fame, with the success of six albums and a marijuana-centric movie, "Up in Smoke." Despite its low budget, the movie earned $44 million at the box office. Two sequels followed, and so did stars volunteering to do cameos in the Cheech and Chong films. Harry Dean Stanton, Paul Reubens, and Cassandra Peterson, AKA Elvira, jumped on board.


Lillian Wells

In the 1940s, scores of aspiring actresses posed for pinup shots for publicity or to earn some cash. Today, we recognize these photos as enduring symbols of American culture of the time. Lillian Wells worked as a model and pinup girl, with dreams of becoming an actress. She finally made it onto the silver screen in "Dead Reckoning," "Framed," and "Down to Earth," but never made it "big" in Hollywood. Her classy black-and-white pin-up photos continue to inspire us today.



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