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
9 Russell Brand- Net Worth: $15 Million
8 Jason Stratham- Net Worth: $30 Million
7 Keifer Sutherland- Net Worth: $65 Million
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
3 Mark Wahlberg- Net Worth: $150 Million
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.