By Isabella Torregiani
1:38pm PST, Mar 5, 2026
Caleb Flynn
Just because you're rich and famous doesn't mean you're above the law. Over the years, many celebrities have spent time behind bars — and
Caleb Flynn is the latest to join the list.
The former
American Idol contestant has been accused of murdering his wife, Ashley Flynn. On the day of the incident, he called police to report a burglary at their home in Tipp City, Ohio, where the couple lived with their two young children. When officers arrived, Ashley was pronounced dead.
"Somebody broke into my home and killed my wife," said the caller, later identified as Caleb. "Please, please hurry. […] She's got three shots to her and blood everywhere."
Several days later, Caleb, who competed on
American Idol in 2013, was arrested and charged with murder, two counts of felonious assault and two counts of tampering with evidence, according to online court records. He has pleaded not guilty.
Caleb isn't the only famous face to have done time. Keep reading to see other Hollywood stars who have worn orange jumpsuits … MORE:
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Martha Stewart
Martha Stewart is just as famous for her stint in prison as she is for her one-pan pasta.
In 2004, the best-selling author and Emmy Award-winning TV host spent five months behind bars after being implicated in an insider-trading scandal.
Stewart became the first female self-made billionaire in the U.S. when her company, Martha Stewart Living Omnimedia, went public in 1999. Just two years later, in December 2001, she ran into trouble after selling her shares in ImClone Systems, a biopharmaceutical firm.
When questioned by investigators, Stewart and her stockbroker, Peter Bacanovic, claimed that they had no insider knowledge behind the sale. Nonetheless, federal prosecutors later charged the pair with using non-public information for the trade and lying to investigators.
A trial followed in early 2004, and Stewart was found guilty of conspiracy, obstruction and two counts of making false statements to federal investigators. She was sentenced to five months in prison and two years of probation.
Tim Allen
Years before he became America's TV dad, Tim Allen was a struggling 25-year-old who served time in federal prison for drug offenses.
On October 2, 1978, Allen organized a $42,000 drug deal at Michigan's Kalamazoo/Battle Creek International Airport. He had copied the idea of hiding drugs in a locker from something he saw on television. However, when the buyer opened the locker and found more than 650 grams of drugs, police quickly surrounded Allen.
It turned out the man Allen had made the deal with was an undercover police officer, who had been watching him for months. On top of that, Michigan had recently passed the "650-lifer law," which sentenced anyone convicted of selling that quantity to life in prison without parole.
Allen pleaded guilty to drug trafficking and provided police with names of other dealers he knew, moving his case to federal court and avoiding Michigan's new law. He served only two years of a three-to-seven-year sentence and was released in 1981.
Sean Penn
In 1987, while on probation,
Sean Penn was arrested for hitting a movie extra on the set of
Colors. He was sentenced to 60 days in jail and served 33, according to
Us Weekly.
The actor reportedly lost his temper when extra
Jeffrey Klein took photos of him and Robert Duvall, swearing and spitting at Klein. When the extra spat back, Penn punched him repeatedly and had to be restrained by crew and cast. Klein was treated for cuts and bruises at an emergency medical center.
Along with his prison sentence, Penn was required to complete a minimum of six months of therapy for his violent behavior.
Felicity Huffman
In 2019,
Felicity Huffman spent 11 days in jail for paying
William "Rick" Singer $15,000 to alter her daughter's SAT scores. She recently spoke about the college admissions scandal, Operation Varsity Blues, in an interview with
Eyewitness News.
"People assume that I went into this looking for a way to cheat the system, and making proverbial criminal deals in back alleys, but that was not the case," Huffman said.
"I worked with a highly recommended college counselor named Rick Singer. I worked with him for a year and trusted him implicitly; he recommended programs and tutors, and he was the expert. And after a year, he started to say, 'Your daughter is not going to get into any of the colleges that she wants to.' And I believed him."
Huffman was one of 50 individuals identified in a federal investigation into Singer's illegal "college counseling" operation, which helped elite families gain admission to prestigious universities.
