Natasha Lyonne is one of those actresses that you truly have to admire. Once the owner of a big, fat paycheck after scoring a role in American Pie, Lyonne suddenly found herself without a job and, due to a nasty illegal substance problem, without any money or a place to live. She was hospitalized and admitted to a rehab facility after suffering serious health issues.
But the strong redhead bounced back. Not only did she manage to kick the bad habit and stay clean, but she also made a fantastic comeback with the wildly popular TV series, Orange is the New Black. And in February 2019, she co-created and starred in Netflix’s Russian Doll, a highly acclaimed, Emmy-nominated series.
Lil’ Kim
Another big-shot celebrity that got caught up in tax evasion was 90's rap queen, Lil' Kim. Apparently, Kim hasn't paid taxes since 2010! That little stunt has the music artist owing more than $126,000 to the IRS in back taxes alone. And the problems don't stop there.
Having the IRS on your back is bad enough, but clearly, Kim didn't think so, since she managed to get sued by her own legal representation. Miss Kim apparently failed to pay them in full for over five years of legal services. Long story short, she lost in court and ended up having to pay nearly $200,000, leaving her broke and lawyer-less.
Dustin Diamond
Maybe the name won't immediately ring a bell, but the popular 1980's American sitcom, Saved by the Bell, will definitely sound familiar. Dustin Diamond played Screech, the lovable geek of California's Bayside High School. Unfortunately, Diamond wasn't as beloved after his Saved by the Bell days, and he struggled for years to find a good-paying acting job.
Diamond hit rock bottom when, in 2001, he filed for bankruptcy and disappeared off the map for a few years. Then, in 2006, he was reportedly selling T-shirts with his face on them to try and raise the money he needed to avoid his house being foreclosed. Unfortunately, Diamond passed away in early 2021 following a cancer diagnosis.
Charlie Sheen
After his debut in the 1984 Cold War drama, Red Dawn, Charlie Sheen rose to fame in a way any actor could only dream of. Being the son of legendary actor Martin Sheen surely didn't hurt, but Charlie definitely pulled his own weight after acting in epic films like Platoon, Wall Street, Major League, Young Guns, and many more. But his biggest break probably came in 2003, when he became one of the stars of the extremely popular TV show, Two and a Half Men.
This role made Sheen one of the highest-paid actors on network TV, being paid $1.8 million per episode! Unfortunately, the ride wouldn't last forever, as he was kicked off the show in 2011 for reckless and lewd behavior. Charlie's finances took a big hit - as the celebrity bad boy owed over $12 million in unpaid debts like legal fees, mortgages, and taxes. And things don't appear to be getting better, as Sheen apparently still owes $5 million in unpaid taxes!
Mark Hamill
Ironically, being the original star of a $10 billion movie franchise doesn't guarantee you're financially set for life. Mark Hamill is the original Luke Skywalker, playing him in the first installment of the epic Star Wars saga, 1980's The Empire Strikes Back. Unfortunately, after the following movie, 1983's Return of the Jedi, Hamill had a hard time finding work.
For nearly 30 years, Hamill was seen by every director and producer out there as Luke Skywalker, and nothing more. After years of doing little more than voice-over work for some animated TV series and a few video games, Hamill got a lucky break in 2015, when he was asked to play Skywalker once again, in The Force Awakens. And judging by his role in subsequent Star Wars films, in 2017 and 2019, this celebrity's paycheck may be rising to what it once was.