Top 10 Interviews That Predicted Celebrities Would Go to Jail

When you're public enemy

A 2011 showdown between Russian oligarchs led to major legal trouble, particularly for this real estate mogul. During a televised economic debate, Polonsky angered former KGB spy Alexander Lebedev. The situation escalated quickly when Lebedev punched Polonsky so hard he fell from his chair. While Lebedev received community service for the attack, it was Polonsky who eventually served time. Just a year after their altercation, Polonsky landed in a Cambodian jail for allegedly assaulting sailing crew members. Later, he faced embezzlement charges and was placed on Interpol’s most wanted list, solidifying his fall from grace.

Despite being considered one of the world’s best boxers, Mike Tyson is no stranger to legal trouble. By 1999, he had already served three years for sexual assault, in addition to his history of juvenile delinquency. Just before his fight with Francois Botha, Tyson had a conversation with sports anchor Russ Salzberg that was so profane and hostile, Salzberg had to cut it short. Unsurprisingly, Tyson’s legal issues didn’t end with that friendly chat. Just a month later, he was sentenced to 12 months in jail for a prior road rage incident, and he’d face a plethora of additional charges in years to come.

Masterson is best known for two things: his sitcom roles and his alarming record of sexual misdeeds. Years before the truth about his actions came to light, Masterson appeared on “Late Night with Conan O'Brien” to promote “That '70s Show.” During the segment, he made a sexual joke during an anecdote to which Conan quipped that he had “heard about [him]” and suspected he’d be caught soon. While it’s unclear exactly what Conan had heard, his remark proved frighteningly accurate; almost two decades later, Masterson was not only caught, but convicted. This moment serves as a stark reminder that sometimes jokes hit closer to reality than we realize.

This ex-film producer’s misconduct was so extensive that it inspired the term “the Weinstein effect,” which helped ignite the

Once beloved for his role as Jamal on “Empire,” Smollett came under fire in 2019 after claiming to be the victim of a hate crime…only for it to be revealed that he had fabricated and staged the entire thing. Just weeks after the supposed attack, Smollett sat down with ABC’s Robin Roberts to recount the details, claiming he was jumped by two men and bombarded with racist and homophobic slurs. Throughout the conversation, he appeared emotional and resolute, standing by his story while criticizing those who doubted him. However, his detractors were proven right, and Smollett was soon convicted of felony disorderly conduct for making false police reports.

It wasn’t until 2021 that R. Kelly – the R&B singer with a notorious history of sexually abusing minors – was finally brought to justice. However, many years earlier in 2008, Kelly showed a talent for dodging tough questions when he was asked about his troubling behavior. During a BET interview with journalist Touré, he was asked whether he liked teenage girls. While the question was straightforward, Kelly’s evasive response raised serious concerns. His reluctance to give a clear answer hinted at the dark reality that would later surface. In hindsight, this exchange feels like an ominous warning of the long-overdue legal reckoning that awaited the singer.

After personal issues led to his dismissal from “Two and a Half Men,” this disgraced actor spoke to several media outlets. But far from clearing his name, Sheen’s attempts to explain himself only left the public more confused, not to mention a little alarmed. In appearances on ABC, NBC, TMZ, and more, Sheen hinted at his chaotic lifestyle and used bizarre phrases like “tiger blood” and “Adonis DNA…” whatever that means. Sheen’s cavalier attitude made it clear that his tumultuous life was on a collision course with the law. [“You can't process me with a normal brain.”] No lies detected.

For much of the late 20th century, Cosby was celebrated as “America’s Dad,” entertaining viewers of all ages on stage and screen. This made it all the more devastating for his fans and supporters when, in 2014, it was revealed that he had spent pretty much his entire career committing horrific sexual assaults. After the world learned of his crimes, a comment he made to Larry King in 1991 took on an especially chilling tone. Cosby’s offhand joke about "Spanish Fly," a substance he claimed would make women more compliant, was initially dismissed as a humorous anecdote. However, in hindsight, it reveals a troubling reference to the heinous accusations that would ultimately lead to Cosby’s conviction.

Unless you live under a rock inside a cave on a faraway planet, you’re likely aware that this popular rapper has been the subject of major controversy – not just once, but over and over again. Among the worst of Combs’ alleged offenses occurred at what he called his “parties,” events which may have included significant unsavory acts. Disturbingly, a comment Combs made in 1999 suggests he realized his actions were reprehensible even then. Speaking to Entertainment Tonight, Combs (known back then as Puff Daddy) mentioned that his parties were becoming legendary and surmised they’d eventually land him in jail. Though the comment came across as a joke (if not a twisted flex), it now seems quite prophetic in light of Combs’ later legal troubles.

Which of these celebrity arrests could you see coming a mile away? Let us know in the comments!