Actors Edition: Top 10 Hollywood Bad Boys

High Life

The laundry list of Hollywood bad boys is long and distinguished. There is more than just late night shenanigans and rehab stints that make this list, it’s also about holding onto your fortune, despite the mischievous mishaps. There are many Tinsel Town heavy weights, such as Humphrey Bogart, James Dean, or even River Phoenix that have come before the living legends on this list. However, what all these collective stars have lost in accruing their bad boy credentials, they have maintained in their unique ability to stay on the cutting edge of film, and kept their adoring fans. It’s a battle of resilience, and unquestionable faith in climbing back up from a life of destruction, conquering addictions, and attitudes that fame can often accommodate and require. Let’s take a look at the some of the living bad boys of Hollywood.

10. Danny Trejo- Net Worth: $8 Million


Trejo lives the bad boy dream. After years of alcohol, drugs and criminal behavior, the “Machete Kills” star crawled from the bottom all the way to the top. He was in and out of prison for nearly 12 years for armed robbery and drug offences before sobering up and becoming the rebel poster boy he is today. Trejo has seemingly lived two lives, one as a down and out criminal, and a more glamorous second, as the quintessential Hollywood tough guy that has made him his fortune and fame. This tough and tattooed star is known for his gritty appearance and boxing skills, along with his checkered past. With a very comfortable $8 million net worth the ex-con has a lot to smile about in his second life.


9. Russell Brand- Net Worth: $15 Million


Brand’s career as an entertainer has sometimes been eclipsed by his drug addictions. The “Forgetting Sarah Marshall” star has been arrested 12 times for numerous criminal activities. Most recently, while filming a movie in New Orleans the comic stole a photographer’s iPhone and angrily hurled it at a nearby law firm’s window. Just two years before the iPhone incident, Bad Boy Brand attacked the paparazzi when he and then fiancée Katy Perry were trying to catch a flight out of LAX. Brand is both candid, and well known for his past drug and alcohol abuse. After being caught by his agent shooting up heroin at a Christmas party, Brand was successfully convinced to turn his life around, and go to rehab. These days he favors meditation over drugs, and although he is clean, his surly demeanor, disgust for authority, and general thirst for trouble has seemingly only grown since he gave up the hard stuff. His career and bank account have also blown up considerably in the past years. Along with being a successful stand-up comedian, radio talk show host and author, Brand has brought his comedy to the big screen in such films as “Forgetting Sarah Marshall”, “Get him to the Greek”, and a remake of the Dudley Moore classic, “Arthur.” One thing is for sure, we can expect to see more shocking, and probably shenanigans from Brand in the years to come.


8. Jason Stratham- Net Worth: $30 Million


Stratham much like Trejo, found a very unconventional vehicle into the acting world. The employment history is long and equally strange for this Englishman; some of the greatest hits include: a black market salesman, member of the British National Diving team, and male model. Through his modeling connections he was linked with Guy Ritchie, and the rest is history. His first major Hollywood endeavor was in Ritchie’s now classic “Lock Stock and Two Smoking Barrels”. The film was of course followed by his sophomore effort “Snatch”, which found Stratham acting beside some of Hollywood’s biggest and brightest stars. Since then, he has made a formidable name for himself in Hollywood, as a quintessential anti-hero. He launched a career as a leading man starting with “The Transporter” which, due to its success, snowballed into two more follow-up films. Stratham has now grown into one of the most sought after action stars in Hollywood. With his street-wise sensibilities, along-side his reputation and ability to perform his own stunts, there will be much more seen and earned from this eccentric addition to our list.


7. Keifer Sutherland- Net Worth: $65 Million


Sutherland was born into Hollywood royalty, the son of the famous actor Donald Sutherland and Canadian actress Shirley Douglas. Appropriately enough his first major film role was in “The Bad Boy” which earned him a Genie nomination for best actor. Although these days Sutherland is best known for his role as Jack Bauer on “24,” he cut his teeth as an 80’s heartthrob in classics like “The Lost Boys”, “Stand by Me”, “Flatliners”, and “Young Guns.” Sutherland is no stranger to the long arm of the law. The “24” star has been picked up for DUI on four separate occasions (1989, 1993, 2004 and 2007). Despite his brushes with the law, Sutherland’s acting career has done nothing but mushroom since his brat pack days. Reportedly, for his work on the highly successful television drama “24” he received $500,000 per episode, making him the highest paid television actor at the time of the show’s original run.


6. Robert Downey Jr. – Net Worth: $85 Million


There is no other Hollywood A-lister with a criminal track record and wallet size that compares to Robert Downey Jr.. The talented but troubled Downey, has had a taste for the fast life since adolescence, and not even nearly a year of hard time in a California state prison and drug rehabilitation center could slow him down. His personal life seemed to mimic that of  “Less than Zero” character for more than a decade after the film wrapped.  Since sobering in the early 2000’s, the “Iron Man” star has become the highest paid actor in Hollywood. Downey has an estimated $85 million net worth and in just the past decade has starred in 6 movies that have grossed over $500 million. Two of those films: “The Avengers” and” Iron Man 3” grossed over a billion at the Box Office. The actor’s unlikely success and resilience despite years of heavy drug abuse, and unparalleled financial dominance in Tinsel Town, makes him unquestionably one of Hollywood’s quintessential bad boys.


5. Charlie Sheen- Net Worth: $125 Million


When it comes to commitment to being as bad as possible, and making sure he’s getting paid to do so, Charlie Sheen outshines most of his contemporaries. Of course, no one will forget Charlie’s 2011 falling out with CBS and the subsequent termination of his contract for his hit television show “Two and a Half Men”. What some forget are his 1998 drug overdose and 2009 domestic assault charge against his then wife Brook Mueller. Despite his nefarious behavior, Sheen does not have any monetary worries as his net worth is an estimated $125 million.


4. Samuel Jackson- Net Worth: $150 Million


Samuel Leroy Jackson defined bad boy sensibilities with his infamous role as Jules Winnfield in Quentin Tarantino’s 1994 crime epic “Pulp Fiction”. Jackson’s on screen persona in “Pulp” doesn’t necessarily mirror his off screen passion for civil rights and commitment to justice. However, Jackson has had his fair share of troubles with drugs and some of the short fallings of fame. When his career was still in its infancy, Jackson was often type cast as a street hardened drug addict or thug. An existence familiar to the star as he battled heroin and cocaine addiction in the 80’s, he was cast as the crack addicted younger brother to Wesley Snipes in the controversial and fantastic Spike Lee joint “Jungle Fever,” a film tackling love and race relations for a more enlightened generation. As his career and personal life have progressed, his range as an actor has expanded generously, and perfectly pronounced his diverse range of drama, comedy and horror. While generally humble and even unassuming about his success, with over 100 films under his belt and a heart and social consciousness that rival his bank account, there is no arguing that conviction and dollars can go hand and hand.


3. Mark Wahlberg- Net Worth: $150 Million


Mark Wahlberg rose to fame in the early 1990’s as the bad-boy rapper Marky Mark. It seems like a lifetime ago that Walberg was flashing us in his Calvin Klein ads, and the actor of today is a far cry from his Funky Bunch days. Wahlberg struggled with drug addiction in his youth (specifically cocaine). He dropped out of school at age 14 and started selling drugs on the streets of Boston. After a string of petty crimes, in 1988, at the age of 16, Wahlberg was sentenced two years in prison for assault. He served 45 days. The rapper turned actor has since cleaned up his act and is now one of the highest paid actors on the Red Carpet. Films like: “Boogie Nights”, “Three Kings”, and “The Perfect Storm” put Wahlberg on the map. The former rapper now has an estimated $150 million net worth and is the fourth highest paid actor in Hollywood. While maintaining a lucrative acting career with recent critical and financial successes like “The Fighter” and “Ted” which earned a staggering $550 million at the box office, there is nowhere to go but up for the former pants dropping celebrity.


2. Sean Penn- Net Worth: $150 Million


This Academy Award winner has had a rebellious demeanor since his early days in Hollywood. Starring in 80’s classics like “Taps”, “Fast Times at Ridgemont High”, and the perfectly appropriate and provocative “Bad Boys”. Like Downey, Penn’s off screen persona seemed to trace that of his bad boy character. Penn always had a deep hatred of the paparazzi, and has been reprimanded on numerous occasions for his violent outbursts towards the press. Most famously, in 1986 while filming “Shanghai Surprise,” Penn found a photographer hiding in his hotel room. Furious with the encroachment on his privacy, he proceeded to dangle the intruder from a nine story hotel room balcony threatening his life. Again, in 1987 he attacked a photographer when he, and then wife Madonna, were bombarded by the paparazzi outside their Central Park West apartment. The actor served 34 days in jail for the incident. The 90’s saw Penn evolve into a cultural icon and voice for social and political justice. His growing demand from directors as a leading man brought films like” Dead Man Walking,” ”Sweet and Lowdown” and “Mystic River.” Penn has calmed his inner rebel a bit in his later years, but the paychecks keep getting fatter.


1. Mel Gibson- Net Worth: $800 Million


With an $800 million net worth and a history of compulsive bad boy behavior, Gibson is unrivaled in his capacity to make a dollar. Gibson claims to have started drinking when he was 13 and his long battle with alcohol has landed him two drinking and driving arrests. He rear ended a car in Ontario, Canada while inebriated and was banned for driving in the country for three months, and of course, no one will forget his infamous 2006 arrest. The incident yielded the actor considerable bad press due to his surly anti-Semitic rant. Although the DUI debacle has sullied his reputation in Hollywood, Gibson still enjoys a high profile and an unrivaled net worth. The unfortunate performance of 2011’s “The Beaver” and 2013’s flop: “Machete Kills” both proved to be critical and box office disappointments. However, although his “Lethal Weapon” days may be behind him the “Braveheart” star has accrued enough money for a small country and the “Road Warrior” can no doubt afford to handle any future legal battles that come his way.