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30 Hollywood Bad Boys We Can't Help But Love

If there's one thing Holywood has no shortage of, it's bad boy actors. Some celebrities try to be (or at least seem like) good role models for their fans... but some do not. Many of them have been arrested for various crimes, while others are known for their lack of upstanding character. But, for some reason, we can’t resist a bad boy, especially a famous one. Even if they’re not the best people off-screen or off-stage, we’re all still drawn to their miscreant charm.

From Charlie Sheen to Sean Penn, there's no saying what the bad boys of Hollywood will get up to next, but no matter what it is, we'll be eagerly awaiting the news. While some of these Hollywood bad boy actors have managed to turn their lives around, others have not had such luck. Regardless of where they are now, their actions haven't hindered our unconditional love for them - not that we aren't rooting for them. Hollywood loves a good redemption story too.

That being said, some of the entries on this list may be controversial, but even if some of their actions are exceedingly questionable, we haven't gotten tired of hearing about these guys. Here are the 30 Hollywood Bad Boys We Can't Help But Love!

Samuel L. Jackson

Samuel L. Jackson

His bad boy persona kicked off with his role as Jules Winnfield in Pulp Fiction in 1994, and he faced his fair share of substance charges some years ago. Yet, in spite of his rough exterior and past, he’s now quite a socially conscious and humble guy. Best of both worlds, right?

In film, Samuel L. Jackson has built a reputation as one bad mutha, but in real life, he's generally a nice guy. We all love him and that's evident by the box office numbers he manages to pull in. Nevertheless, he's probably a guy you wouldn't want to mess with or say what? to. 

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Mark Wahlberg

Mark Wahlberg

He’s no longer known as the rapper, Marky Mark, who struggled with substance abuse during his teenage years. Wahlberg has cleaned up his act since then, and he is now one of the most successful bad boy actors in the business with box office hits like Ted and Transformers under his belt.

He may be just 5'8" but his intimidating on-screen presence has made him a huge success as a Hollywood tough guy. Of course, 80% of that probably has to do with his hard Boston accent and the other 20% is the fact that he's definitely been in a fight or two. If he says, "Say hello to your mother for me.," you better be sure you are going to do it.

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Jude Law

Jude Law

You would probably think Jude Law is a stand-up guy based on his alluring British accent and work in films like The Holiday, but he's made some major real-life lapses in judgement. He may not have had any run-ins with the law, but he made quite a name for himself after the infamous affair with his children’s nanny resulted in his breakup with Sienna Miller. 

But despite his shortcomings, he's also proven himself as quite the humanitarian, donating to a number of different children's charities. And on top of that, we forgive him because he's a phenomenal actor, capable of transforming from an absolutely lovable lady's man to a despicable hit man, seamlessly. Now, he's set to star in a Star Wars project for Disney Plus: Star Wars: Skeleton Crew.

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Sean Penn

Sean Penn

The Fast Times at Ridgemont High and Milk actor is perhaps most widely known for his hatred of the paparazzi. Specifically for dangling a photographer from his ninth story hotel balcony after he caught the man hiding in his room. That reaction was perhaps a little extreme, but you have to admit that you’d be pretty angry too if you caught a stranger hiding in your room!

On top of all that, he's assaulted a newspaper correspondent, songwriter David Wolinski at a nightclub, a film extra,  and photographer Frank Mateljan. Clearly, he has quite the anger issues but that doesn't change the fact that he's a great actor. We just gotta ask, "Hey Bud, what's your problem?"

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Christian Bale

Christian Bale

He saves the day and fights the villains as Batman on screen, but his rap sheet in real life isn’t quite so blemish-free. He’s widely known for his bad temper, but he kind of redeemed himself by visiting victims of the Aurora shooting who were attacked during a showing of The Dark Knight Rises.

The actor is best known for his amazing body transformations, gaining a tremendous amount of weight for a role and then dropping a ton of weight on a whim. He went from being morbidly skinny in The Machinist to his bulked-up role in Batman Begins. And now he's an Academy-Award nominated actor so that method acting seems to have paid off. 

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Robert Downey, Jr.

Robert Downey, Jr.

He was THE Hollywood bad boy actor before he turned over a new leaf, leaving the crippling addiction and crime of his younger years behind him. He’s now the highest-paid actor in Hollywood, starring in films such as Iron ManSherlock Holmes and The Avengers. The multiple Academy Award-nominated actor is one of the best actors working in Hollywood.

Recently, he lost his father Robert Downey Sr. who was more or less the cause of his past issues, having introduced him to a number of illegal substances in his youth, but RDJ no longer holds a grudge, having made his father a subject of a documentary on Netflix - simply titled Sr.

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Mel Gibson

Mel Gibson

His infamous drinking problem and anti-semitic rants have caused him to lose some fans over the years, but he doesn’t seem to care that much about what people think of him. Being one of the most famous actors/directors in the world, claiming a fortune of over $800 million dollars, and having Braveheart and The Passion of the Christ on his resume, we can understand why.

Mel Gibson still remains a subject of controversy and we can't really speak for his real-life views to this day, but we can safely say that he's still a man of talent if nothing else. That's compelling enough of a reason to still not mind seeing him on screen or behind the camera. 

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Charlie Sheen

Charlie Sheen

Does he really even need a caption? His infamous firing from Two and a Half Men echoed around the world along with the rants and violent acts that followed, causing him to look like a true lunatic. We hope the Men at Work actor has received some help by now.

While you could say his career is in question at this point, Charlie Sheen has never stopped entertaining us. He manages to stay in the spotlight, no matter what he does and we are anxiously awaiting what he'll do next. How he is still alive at this point is a mystery, but it must have to do with all that tiger blood.

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Johnny Depp

Johnny Depp

As he rose to stardom, Depp’s younger years were infamously filled with endless partying and substance abuse. His roles in Edward Scissorhands, Sweeney Todd, and Transcendence have helped carry on his mysterious, dark onscreen personality, even though he’s now a father. In recent years, he's oncer again been a subject of controversy.

With accusations of substance abuse and domestic violence from ex-Amber Heard and a defamation lawsuit from Depp himself, it's hard to say what the exact truth is other than the fact that none of them are quite innocent. Nevertheless, the past is in the past and we can't wait for Johnny Depp to get his life back.

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Colin Farrell

Colin Farrell

He loves to smoke, drink, and curse onscreen and off, and he’s actually been sued twice for alleged harassment (both cases were dropped). Yet, all those characteristics combined with his Irish accent and his disheveled look make for one irresistible face that you can catch in True Detective, Total Recall, and In Bruges.

Colin Farrell has a reputation among the bad boy actors who don't give a flying fig about what comes out of their mouths and that's precisely what we love about him. Well, that and that irresistible Irish accent. We can't wait to see him back as the Penguin in The Batman spinoff series titled - you guessed it - The Penguin.

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John Mayer

John Mayer

His songs, such as, “Your Body is a Wonderland” and “Free Fallin," may make you fall to your knees, but his personality sure won’t. He’s widely known to be less than friendly in person and has broken the hearts of both the beloved Taylor Swift, and Katy Perry in recent years.

The sad boi with the guitar has had numerous other troubles over the years including alcoholism which is said to be behind him after a six-day hangover that occurred after Drake's 30th birthday. He's also not afraid to kiss and tell or use racially insensitive words. We still love his music though - but maybe he should stay quiet unless he's belting some tunes.

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Nicolas Cage

Nicolas Cage

Nicolas Cage has been acting just as crazy off-screen as he has been acting on-screen. He may not be the first actor you think of when it comes to bad boy actors, but considering he’s been arrested multiple times and has also had a run-in with the IRS, its fair to put him on this list.

In her 2008 memoir, Send Your Roses, Kathleen Turner detailed a time when he was arrested twice for DUI while filming Peggy Sue Got Married. In 2011, he was arrested under suspicion of domestic abuse, public toxication and disturbing the peace. But his biggest troubles came in 2009, when the IRS discovered he owed over $6 million in taxes.

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Russell Brand

Russell Brand

Another Katy Perry ex, Russell Brand, hasn’t exactly made his disgust for authority and yearning for trouble any secret. He’s apparently given up the substances for now, but his surly attitude hasn’t changed much. His eccentricities come through quite well on screen, though, particularly in films like Rock of Ages and Forgetting Sarah Marshall.

The quick-witted Russell Brand is now the host of his very own podcast and YouTube channel which often questions the establishment, presenting all sorts of conspiracy theories, even related to COVID denialism.  Whether he's full of it or not, we still can't help but love how enthusiastic he seems just about - everything. 

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Alec Baldwin

Alec Baldwin

Alec Baldwin has had his share of bad-boy incidents throughout his career and accidentally unaliving someone on the set of a movie isn’t even what we are talking about. He’s publicly spoken ill of his ex and called his daughter a "rude, thoughtless little pig" – but that’s all just from his personal life.

In 1995, he assaulted a photographer outside his Los Angeles home after taking a photo of Baldwin and his daughter. On top of that, in 2011, he broke airline rules, becoming belligerent on a flight, which resulted in him getting removed from the plane. And if he isn’t in jail soon, hopefully, he can stay off the police radar for the remainder of his life.

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Leonardo DiCaprio

Leonardo DiCaprio

Leonardo DiCaprio may not be a bad boy actor per se. After all, there’s nothing bad about promoting climate change awareness, but you have to admit he’s pretty reckless when it comes to women’s hearts. With a reputation for bringing young girls on his yachts and dumping them after they turn 25, he’s become a punchline in terms of his love life.

Nevertheless, the bachelor doesn’t seem to care what people think of him as he’s not out to settle down yet. One thing we can say about him is that at least he isn’t going around assaulting people, so he has that going for him. While he might not be pleased being described as a womanizer, he doesn’t mind being commended for his acting abilities – which we do.

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Kanye West

Kanye West

Kanye West is funnier than he is an actual bad boy, but his ego is so large that he couldn’t care any less about what people thought of him, even if he tried - so you have to admire that. From the moment he randomly blurted out “George Bush doesn’t care about black people” to the Taylor Swift stunt, Kanye West has been keeping himself in the spotlight.

Even if he hasn’t been producing the hit like he did over a decade ago, he still manages to keep people interested. Running for president might have been his most ambitious stunt yet, but nothing came of that, so it was harmless. But don’t worry, word is out that he intends to run for president again.

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Eminem

Eminem

Eminem has produced a number of incredible hits including arguably one of the best rap songs of all time, “Lose Yourself,” and that’s why we love him. But when it comes to controversy, the artist does not shy away from it – having had numerous ups and downs during his career.

He’s had feuds with numerous artists over the years from Christina Aguilera to Machine Gun Kelly. He’s also had multiple run-ins with the law, including a drive-by incident when he was 20, an assault in 2000, threatening the president, and much more. On top of that, his past lyrics have been accused of being homophobic, but since then he’s sought to shed that image.

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Johnny Knoxville

Johnny Knoxville

Star of Jackass has built a reputation of being wild and outrageous, pulling pranks for the amusement of audiences. Not caring what people think of him helped him make a career out of it. While 15 year old boys might have enjoyed his antics, not everyone has, which is why he ended up getting sued.

The lawsuit came from Khalil Khan, the unsuspecting repairman who was faced with a traumatizing scene that ended in him being threatened with assault, having his vehicle towed and a warning that he could face jail for being in possession of an illegal substance. But despite the lawsuit, Knoxville plans to carry on as usual.

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Russell Crowe

Russell Crowe

Maximus himself, Russell Crowe, has the same bad boy attitude in real life that he has in the gladiatorial arena. He doesn’t care what people think of him and that shows through with his tremendous anger issues. In fact, we’re guessing he didn’t really have to do any acting when it came to Unhinged.

In 1999, he got into an altercation with a woman at a hotel. In 2002, he fought with a producer at the BAFTA Awards and then got into a brawl with Eric Watson later that year. Then, in 2005, he famously threw a telephone at a hotel concierge. The incident negatively impacted his career but certainly didn’t put him out of work.

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Shia LaBeouf

Shia LaBeouf

Shia LaBeouf started out as one of our favorite Disney Channel stars and grew into a talented actor as an adult, but his career took a bit of a dive due to all his legal troubles. None of that has really turned us off from him completely though, despite the many legal troubles he’s been through in recent years.

Having been accused of plagiarism, multiple accounts of disorderly conduct, battery and theft. Alcohol, in particular, has been a huge problem for LaBeouf in the past but that seems to be true for a lot of child actors. On top of all that though, he’s been accused of physical and emotional abuse, which he looks back at with much regret. We are rooting for him to fully turn things around. What are you waiting for, Shia? Just do it!

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Nick Nolte

Nick Nolte

At this point, Nick Nolte is probably best known for his mugshot, even though he’s a terrific actor. His heyday was in the ‘80s and ‘90s but even then he had a reputation for being a bad boy. Back in 1965, he was arrested for counterfeiting documents, and he would have faced a 45-year sentence if it hadn’t been suspended.

In 2002, he was arrested for DUI and also claimed to have given up drinking after that. Since then, he’s been nominated for an Academy Award, and Golden Globe, and has even made his way to one of the biggest franchises known to man: Star Wars, starring as Kuiil in the hit series The Mandalorian.

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Jonathan Rhys Meyers

Jonathan Rhys Meyers

Jonathan Rhys Meyers, probably best known for his role as Henry VIII in The Tudors, has also starred in notable films like Match Point, Mission: Impossible III, and Bend It Like Beckham. But as much acclaim as the actor has been met with, he’s equally found himself faced with much criticism.

Since, before 2007, he’s had trouble with alcohol and a history of suicide attempts. He’s physically assaulted employees and verbally harassed them as well – all as a result of his alcoholism. But of course, it doesn’t excuse his bad boy behavior, merely explains it. His most recent incident occurred in 2020 when he crashed his car in Malibu. He was charged with two drunk driving offenses.

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Richard Harris

Richard Harris

Before he became Dumbledore, Richard Harris was one of the original bad boy actors of Hollywood. He was a staunch supporter of the Irish Republican Army and an overall h*llraiser caught in the heavy drinking scene as well as other illicit substances. He even once through a brick through somebody and purchased a Rolls Royce and forgot about it.

In one particular altercation, according to his son Jared Harris, he told a woman, “I can forgive ignorance, and I can even forgive rudeness, but I can’t forgive ugliness and you are the ugliest woman I have ever seen, now f*** off.” After her boyfriend, intervened, he assaulted the man, knocking him out.

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John McEnroe

John McEnroe

John McEnroe is not only known for his skills on the tennis court but his frequently confrontational behavior on the court. His frequent outbursts have gotten him in trouble a number of times, but we admittedly have been entertained by his antics. His larger-than-life personality has even landed him appearances on television and in film.

Despite his bad boy behavior on the court, his temper hasn’t gotten him in much trouble in real life, which makes us believe that, in part, it was probably all for show. After all, the only bad publicity is no publicity. There’s just no denying he’s a tennis icon. We are completely serious.

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Ozzy Osbourne

Ozzy Osbourne

Ozzy Osbourne has been a subject of controversy for many years and not just over his personal life. As the lead singer of Black Sabbath, he’s been accused of having a negative influence on teenagers with religious groups suggesting that he promotes Satanism. And then there was the time he bit a bat on stage with his teeth.

His personal life has been marked by continuous substance and alcohol use, which has caused a number of health issues and multiple cases of animal abuse. Nevertheless, we all enjoyed the antics of his family on The Osbournes and all the classic hits he produced as part of Black Sabbath and his solo career.

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Jack Nicholson

Jack Nicholson

Jack Nicholson has had a reputation for his womanizing ways. Jumping from woman to woman, the bad boy actor has claimed to be with over 2,000 different women. Even having fathered six children among five different women, he’s only been married once which only lasted about six years. In the 1990s he reached his lowest point.

Not only did he destroy someone’s car with a golf club in 1994, but he also assaulted a woman he owed money to in exchange for…ummm…services. But despite his behavior, he’s still one of the best actors of his generation with an on-screen charisma that very few actors have been able to match.

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Hugh Grant

Hugh Grant

Hugh Grant may be a boy scout on camera in his many rom-coms over the years, but behind the camera, it's another story. Hugh Grant has been caught with streetwalkers, assaulted a paparazzo, and fathered multiple children with women he wasn’t married to, cheating on one with the other.

In terms of his work life, he doesn’t seem to fare much better when it comes to his bad boy persona. Both Drew Barrymore and Robert Downey Jr. found working with the actor to be difficult. But of course, when it comes to RDJ, they are both bad boy actors, so perhaps there was a bit of a personality clash?

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Christian Slater

Christian Slater

From early on in his career, Christian Slater has maintained a reputation as a bad boy. He’s struggled with substance abuse and alcoholism. He was arrested in 1989 for drunk driving and in 1994, he was found in possession of a weapon that he tried to bring aboard a commercial plane.

Then, in 1997, he assaulted his girlfriend and a police officer while under the influence of numerous substances. In 2005, a woman alleged she was assaulted by him, but the charges were later dropped. Since then, he’s managed to keep a low-profile, having finally settled down with a woman, Brittany Lopez, whom he married in 2013.

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Mickey Rourke

Mickey Rourke

Mickey Rourke was once one of the best-looking men in Hollywood before his unconventional lifestyle messed up his face. Starting off as an amateur boxer, he turned to acting after his teen years. But having been difficult to work with, Hollywood got fed up with him. As a result, he returned to boxing in the early ‘90s.

Suffering from multiple injuries and undergoing multiple surgeries, transformed his appearance. While he made some unsuccessful attempts to return to Hollywood, he couldn’t make his big comeback until 2005 for the film Sin City. Following that, he won us all back as Randy 'The Ram' Robinson in the 2008 film, The Wrestler for which he earned an Academy Award nomination.

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Marlon Brando

Marlon Brando

Marlon Brando is another one of Hollywood’s original bad boy actors. Notoriously difficult to work with, he never cared what others thought of him, even if it was nothing but praise – refusing to collect his Best Actor Oscar for The Godfather. And on top of that, he was known for his public outbursts and rock-and-roll attitude.

His personal life was also quite rocky. He had a large number of partners and was even a father to 11 children with different women. Brando himself claimed to have had an affair with Marilyn Monroe as among the women he had been with. He was married three times but never married again after his third divorce in 1972.

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