Hollywood bad boys never understood the meaning of the word “rules” because they never abided by any. The world loved them for it, rewatching and relistening to the movies and music they’ve made over and over again.
Here some of the most recognizable “bad boys,” known for their reputations as well as the art they made.
Welcome to the Hollywood bad boys club! This actor is most recognizable for his roles as adventurer Indiana Jones (pictured here) and Han Solo in the Star Wars franchise. Known for his lone wolf, “cowboyesque” attitude, Han Solo was the captain of the Millennium Falcon and leader of the Rebel Alliance.
Han Solo is also known for the onscreen romance with Carrie Fisher’s character, Princess Leia Organa.
Little did fans know when Star Wars first came onto the scene in the late ‘70s that Ford and Fisher had a real life romance that wasn’t that romantic …
Their affair started after a drunken cast and crew party when Ford was married with children, Fisher detailed in her memoir Princess Diarist. Scandalous!
He comes from “Hollywood royalty,” his father being the famous Henry Fonda and his sister Jane Fonda. Fonda’s best known for his role as Wyatt, the stars and stripes get-up wearing biker in Easy Rider.
The film co-stars Dennis Hopper as Billy, a fringe-jacket wearing biker who travels with Wyatt to New Orleans.
After the 1969 film, Fonda more or less stayed out of the spotlight until his role as a reserved beekeeper in Ulee’s Gold, says a report in Independent. Until then, he “bought a yacht and led a life of excess for the next decade, never (equaling) the success or esteem of Easy Rider.”
Thomas William Selleck, known professionally as Tom Selleck, is perhaps best known for his role as private investigator Thomas Magnum in Magnum P.I.
It was a role that might have cost him the role of Indiana Jones in Raiders of the Lost Ark, which went to fellow actor Harrison Ford.
Selleck is known as a “man’s man,” a rugged actor that plays the tough guy roles. Thus qualifying him for entrance to the Hollywood bad boys list.
He’s also known for being a heartthrob among audiences, having been selected by People magazine in 1998 as one of “50 Most Beautiful People.”
Actor Burt Reynolds was discovered working on the set of Mister Roberts in New York City, NY, then went on to shows like Gunsmoke and Hawk.
He was best known as “both a rugged action figure and then as a wisecracking, Southern type of ‘good ol’ boy,’” reads his bio on IMDb.
Not only did Reynolds have that bad boy edge, he possessed great comedic timing and acting skills.
“Burt has tremendous comic talent,” Jon Voight, Reynolds’ Deliverance co-star, told Vanity Fair in 2015. “He established a new light-comedy form. Nobody had ever done the good-ol’-boy, Huck Finn thing.”
Peter Fonda’s Easy Rider co-star, Dennis Hopper, was basically blacklisted in Hollywood after talking back to Louis B. Meyer. However, Hopper managed to appear in over 100 films during his 50 year career. It was that rebel attitude that drew fans in, however.
He started off with stage work but then landed a role in Rebel Without A Cause.
On set, Hopper became pals with fellow bad boy actor, James Dean.
John Farr wrote in Huffington Post: “There’s always an intriguing danger lurking behind his lazy, laconic Midwestern drawl … He projects the spirit of a hellion- slightly erratic and unhinged perhaps, but also refreshingly honest, authentic and brilliantly alive.”
Whether you love him or hate him, one thing is for sure: Actor Marlon Brando lived a wild and fast life.
He’s likely best known as the Godfather in The Godfather series, but was a total Hollywood stud before that iconic role.
Brando made waves in films like A Streetcar Named Desire and On the Waterfront.
Besides being a heartthrob on-screen, Brando was known as a womanizer. There’s proof too — he was the father of 11 children. (And no, they don’t all have the same mom …)
Once Upon a Time in Hollywood director Quentin Tarantino drew some flack from Bruce Lee’s daughter, Shannon, for portraying the late actor (played by Mike Moh in the film) as “arrogant.”
Tarantino stands by the portrayal, saying that Lee really was arrogant in real life, reads a report in IndieWire.
Regardless, the martial arts master’s reputation has grown to mythological levels throughout the years.
He was a rebel in his own right, embracing his Hong Kong heritage. He embodied all the classic definitions of a star, however.
“Men wanted to be him and women wanted to be with him,” wrote biographer Matthew Polly.
Often called “the King of Cool,” Steve McQueen was known for his antihero persona.
McQueen’s first leading role was in The Blob (1958). He quickly rose to stardom, snagging mostly action movie roles. He was in The St. Louis Bank Robbery, Never So Few, The Magnificent Seven, The Great Escape, and more.
McQueen was known for his love of racing, saying “racing is life. Anything before or after is just waiting.”
He tragically passed away at age 50 from a rare lung cancer. McQueen tried to cure it with various treatments (some unorthodox) to no avail.
Singer and actor Frank Sinatra was the “original heartthrob,” writes Melina Glusac in a 2018 Insider report. Like Steve McQueen, Sinatra also had a nickname — “Ol’ Blue Eyes,” named so after his dreamy baby blues.
“The United States is now in the midst of one of those remarkable phenomena of mass hysteria,” reads a 1945 report in The Guardian.
“Mr. Frank Sinatra… is inspiring extraordinary personal devotion on the part of many thousands of young people,” they continue. (Namely, teenage girls.)
Sinatra is also known for his ties to the Mafia — the FBI actually tracked the crooner for 40 years, reads an entry on History.com. (Now that definitely makes him a member of the Hollywood bad boys!)
Actor Clint Eastwood first got his start starring in B movies like Revenge of the Creature and Tarantula and digging swimming pools to support himself.
It was the TV show Rawhide that made Eastwood recognizable to viewers but the A Fistful of Dollars movie series truly launched his career.
Then of course there’s the Dirty Harry franchise where he stars as police inspector “Dirty” Harry Callahan.
Eastwood is known for playing tough guy characters. Off screen, he stands out in Hollywood for his political views and opinions — rebellious for a “left-leaning” town!
James Byron Dean was born in the small Midwest town of Marion, Indiana. His mother died when he was 9 years old, and Dean moved back and forth between Indiana and California.
Upon returning to California, Dean studied at UCLA and got into acting. He moved to NYC to pursue acting.
Dean was known for his brief yet spectacular career and well as being the embodiment of the film he starred in, Rebel Without a Cause (basically the king of Hollywood bad boys). He represented the rebellious 1950s youth, reads his licensing website.
He died tragically young in a car crash in September 1955.
The “Man in Black,” as he’s often called, had a long and storied career. He was known for his tough guy attitude, overcoming adversity, iconic songs like “I Walk the Line” and “Ring of Fire,” and relationship with fellow country star June Carter.
Johnny Cash’s rise to stardom wasn’t easy, however.
Born to Arkansas sharecroppers in the midst of the Great Depression, his “hardscrabble life” informed his life and career, reads the bio on his website. Before breaking into Memphis’ music scene, Cash worked in the U.S. Air Force, a factory, and as a salesman.
There were some reports of singer-songwriter Elvis Costello having cancer in 2018 but those were — thankfully — severely overblown. The crooner is alive and well, having recently put out his new album Look Now.
Although he insists he’s “not a rockstar,” he’s known for bangers like “Allison” and “Pump It Up.”
Born Declan Patrick Aloysius Macmanus (say that three times fast) in London, U.K., he got into the music industry via London’s pub scenes.
He became known as the “angriest man in music,” writing songs critical of society like “Radio Radio.”
Scottish actor Sir Sean Connery is known for his distinguishable accent as well as being the original actor to play the womanizing spy James Bond in the 007 franchise.
Connery came from a humble background, having been born in Edinburgh, Scotland to a cleaning lady and factory work/truck driver.
He started to pursue acting at age 23 and scored his first major movie role in No Road Back (1957), reads his IMDb profile. Connery’s breakthrough was, of course, playing James Bond in Dr. No (1962).
Connery’s storied career awarded him various accolades, like being knighted.
Actor Humphrey Bogart was famous for the swagger and tough guy attitude his characters that he radiated on screen.
When he was young, Bogart got expelled from his high school Philips Academy (as Hollywood bad boys often do) and joined the U.S. Navy Reserve.
Bogart started his acting career with stage performances and acted in minor films. He started making waves in 1941, says his IMDb page, with iconic movies like Casablanca, The Big Sleep, and Key Largo.
Bogart usually appeared as a gangster or a brooding, mysterious character in his films.
“Mickey Rooney (Joseph Yule) was an enfant terrible, brilliant, talented, but driven and erratic,” Stuart Lenig wrote in the Columbia Daily Herald.
After being catapulted into stardom with Boy’s Town and Young Tom Edison, Rooney made more than $12 million. However, he blew it all after making unwise life choices like gambling in Vegas.
Rooney was also married eight times, had nine kids, 19 grandchildren, and then who knows how many great-grandchildren.
Aljean Harmetz wrote in the New York Times that he was “impulsive, recklessly extravagant, mercurial and addicted to playing the ponies and shooting craps, he attacked life as though it were a six-course dinner.”
“Perhaps no one was better known in Hollywood for playing a swashbuckling hero than Errol Flynn, the original Robin Hood circa 1938,” writes Melina Glusac in Insider.
Unlike the hero he portrayed on screen, actor Errol Flynn led a lavish lifestyle often rife with excessive drinking.
A TCM biography describes Flynn having had a “tumultuous marriage,” affairs outside of his marriage (with both genders), and “tabloid-scented biographies.”
Sounds like Flynn was busy both on screen and off screen during his heydays — namely the 1930s and 1940s.
Ah yes, the mysterious “man who fell to Earth.”
Singer-songwriter and actor David Bowie hailed from the United Kingdom, but seemed like an unearthly being to his fans and critics. He was best known for hits like “Ziggy Stardust” and “Rebel Rebel” as well as movies like Labyrinth.
The late singer always kept fans guessing, whether it was who he was attracted to, what his politics were, what his religion was, etc.
Bowie also shocked audiences with his gender-bending, tight get-up worn for performances, music videos, and on the street. “Rebel Rebel” indeed!
“The Prince of Hollywood,” “the Pro,” “Boss” — whatever you want to call him, the fact is that Beatty was one of the most seductive actors in 20th century Hollywood.
Warren Beatty is famous for movies like Bonnie and Clyde (in which he played Clyde Barrow), Bulworth, and Reds.
Beatty, who was known for his playboy antics and womanizing ways, shocked the media when he settled down with his co-star from the film Bugsy — Annette Bening.
Their long time marriage garnered a lot of controversies, seeing as there is a shocking 21-year age difference between the two.
“I am the lizard king. I can do anything./Whoever controls the media, controls the mind./No one here gets out alive,” singer and poet Jim Morrison once crooned.
Not necessary part of the “Hollywood bad boys” club but definitely a “bad boy, fans loved Morrison’s unique singing voice and spellbinding lyrics but also romanticized the “live fast die young” lifestyle.
Often an abuser of psychoactive substances, Morrison and his longtime partner Pamela Courson embodied the spirit of the sixties. Angie Pamela writes of that hedonistic lifestyle in Cultura Colectiva: “a life of excess that focused on the present without showing any concern for the future, and above all, the pursuit of pleasure.”
Again, not really part of the “Hollywood bad boys” club per say, reggae musician Peter Tosh still possessed that rebellious spirit!
He came onto the world stage as both an activist and artist via Jamaica. You can guess what one of the causes he fought for was judging by the name of his 1976 release — Legalize It! The herb in question was A-OK for Rastafarians but illegal elsewhere.
“Peter was no stranger to oppression in his homeland and knew the fight for legalization and equal rights well,” reads the bio on his website. “His music served as a catalyst for a generation to fight for what they believed in.”
British musician John Lennon is best known as one fourth of rock band, The Beatles and for his solo work.
Lennon had a rough upbringing which generated anger “that he sublimated with brilliance and difficulty and an intense need for human connection” reads an entry in Encyclopaedia Britannica.
Lennon was separated from his parents at age 5 and his biological mother died when he was an adolescent.
Lennon began making his political leanings known, particularly his anti-war and feminist sentiments. Because of his anti-Vietnam War activism, the administration at the time wanted to deport him.
Born Robert Allen Zimmerman, singer-songwriter Bob Dylan has been active in music since the 1960s. Well into his 70s, he’s now embarking on a tour in 2020. Good for you, Bob!
Dylan is responsible for a lot of well known protest songs like “Blowin’ in the Wind” and “Hurricane.”
Starting out, Dylan mostly stuck to the folk music scene. But he wasn’t afraid to piss off his fans by “going electric,” making country when psychedelic was popular, or turning to religious music.
Clearly, Dylan’s gonna do what Dylan’s gonna do.
Let’s just say that Iggy Pop (born James Newell Osterberg, Jr.) was punk before punk was punk!
Singer Iggy Pop was known not only for songs like “Success” and “I Wanna Be Your Dog,” but for his wild onstage performances. Shows were awash with frightened excitement, as fans never knew what he would do next.
An electric lead singer, Iggy Pop didn’t care about landing singles on the radio and once partied so hard he landed in the mental hospital.
Iggy Pop is still going strong today, even getting more commercial and earning the money he didn’t make back in the day.
“Joe Strummer spent his life smashing musical and cultural boundaries both as the singer of The Clash and as a solo artist,” reads the bio on his website.
Strummer and his band put out some of the most iconic protest songs — much like Bob Dylan in slide number 22 — like “Know Your Rights.”
“It was Strummer’s politically charged lyrics that helped bring punk to the masses,” reads his bio on his website. “Calling out social injustices and giving a voice to the struggles of the working class, his lyrics struck a chord with legions of fans and the press alike.”
“It’s a miracle the notoriously debaucherous Rolling Stones guitarist made it into old age,” writes Ryan Bort in a 2014 report in Esquire.
Much like Rolling Stones lead singer Mick Jagger, Richards also partied hard and had a great many lady friends and love children.
Richards and the rest of the Stones shocked prim and proper England with their dress — long hair, earrings, tight pants, and scarves — and anti-authority, rebel attitude.
Richards was the true punk though: When Jagger was knighted, the guitarist scoffed.
“It’s a shoddy award,” he was reported saying.
As most Hollywood bad boys would say: “Frankly my dear, I don’t give a damn.”
(Side note: How could Scarlett O’Hara dump Clark Gable’s character Rhett Butler again and again for Leslie Howard? I support Rhett’s dramatic mic drop at the end of the flip.)
Clark Gable starred in some of the biggest movies of our time, like Gone With the Wind, making women swoon (except for Scarlett O’Hara).
Doris Day put it best: “He was as masculine as any man I’ve ever known, and as much a little boy … it was this combination that had such a devastating effect on women.
It was actor William Holden’s role in the 1939 movie Golden Boy that would take him to stardom, reads his 1981 obit in the Los Angeles Times. He later took up playing some “hard-bitten” characters in The Bridge On the River Kwai and Stalag 17.
Holden ended up serving in World War II. He didn’t see action but became a first lieutenant upon graduation from Army Air Force Officers School.
He dipped out of the public eye, living in his homes in Switzerland and Kenya. Holden was a conservationist, helping to preserve big game habitats in Africa.
After taking a leave of absence to raise his children as a single father, Rick Moranis is returning to acting for Shrunk, the sequel to Honey, I Shrunk the Kids. Although he stepped away from onscreen acting, he still did voice over work.
(Perhaps you heard him in Disney films like Brother Bear and The Animated Adventures of Bob & Doug McKenzie?)
He first became a household name with appearances in Ghostbusters, Spaceballs, Honey I Shrunk the Kids, and Little Shop of Horrors (featured in this photo here).
Blake, John. CNN. July 7, 2018. “New Bruce Lee bio debunks myths about the ‘kung fu Jesus.’”
Blakemore, Erin. History. May 14, 2018. “Frank Sinatra’s Mob Ties and Other Secrets from His FBI File.”
Bort, Ryan. Esquire. December 18, 2014. “The Rebellious Cool of Keith Richards.”
Christgau, Robert. Encyclopaedia Britannica. “John Lennon.” Accessed February 9, 2020.
D’Allessandro, Anthony. Deadline. February 12, 2020. “Rick Moranis Closes Deal To Return To ‘Honey, I Shrunk The Kids’ Franchise With ‘Shrunk’ At Disney.”
Farr, John. HuffPost. May 28, 2010. “Hollywood’s Glorious Bad Boy: A Tribute to Dennis Hopper.”
Glusac, Melina. Insider. February 11, 2019. “26 heartthrobs from the golden age of Hollywood.”
Hiatt, Brian. RollingStone magazine. November 13, 2018. “Elvis Costello on His New Album, Mortality and His Musical Evolution.”
IMDb.com. Accessed March 4, 2020.
JamesDean.com. “Biography.” Accessed March 5, 2020.
JoeStrummer.com. “Joe Strummer.” Accessed March 9, 2020.
JohnnyCash.com. “Biography.” Accessed March 5, 2020.
Kashner, Sam. Vanity Fair. October 6, 2016. “Six Decades In, Warren Beatty Is Still Seducing Hollywood.”
Love, Keith. Los Angeles Times. November 17, 1981. “From the Archives: Actor William Holden Found Dead at Home.”
Pamela, Angie. Cultura Colectiva. February 20, 2020. “The Destructive Love Story Of Jim Morrison And Pamela Courson.”
Robinson, Tasha. The Verge. January 3, 2017. “Carrie Fisher’s last Harrison Ford story isn’t romantic, it’s tragic.”
Schudel, Matt. Independent. August 18, 2019. “Peter Fonda: Easy Rider star and scion of Hollywood royalty.”
Sharf, Zack. IndieWire. August 17, 2019. “Quentin Tarantino Defends ‘Hollywood’ Bruce Lee Fight From Claims It Mocks the Late Action Star.”
The Guardian. January 10, 1945. “Frank Sinatra and the ‘bobby-soxers.’”
Wells, Samantha. Ninja Journalist. September 22, 2019. “Tom Selleck Makes A Surprising Family Announcement.”
Zeman, Ned. Vanity Fair. December 2015. “Burt Reynolds Isn’t Broke, but He’s Got a Few Regrets.”
This article was originally published on Finance101: You’ll swoon over these vintage Hollywood bad boys.
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