Mug shots

Long before his rise to Rat Pack fame, Frank Sinatra found himself on the wrong side of the law. In 1938, at just 23 years old, he was arrested by the sheriff of Bergen County, New Jersey, on charges of “seduction”—a now-obsolete crime tied to having relations with a woman of “good repute” under the promise of marriage. When it was later revealed the woman was married, the charge was changed to adultery. Ultimately, both charges were dismissed. The incident remains one of the more bizarre footnotes in the crooner’s legendary career.

In October 1965, music legend Johnny Cash was taken into custody by U.S. Customs officials after authorities found a large quantity of prescription stimulants and tranquilizers in his luggage. The country icon had just returned by plane from Juarez, Mexico, when he was detained and spent the night in a jail cell in El Paso, Texas. Cash later pleaded guilty to a misdemeanor drug possession charge, resulting in a $1,000 fine and a 30-day suspended sentence.

In October 1978, Sid Vicious, bassist of the Sex Pistols and a figurehead of punk rebellion, was arrested in New York City for the murder of his girlfriend, Nancy Spungen. Spungen was found stabbed to death in the couple’s room at the Chelsea Hotel. Vicious initially confessed but later recanted, claiming he had no memory of the night due to heavy drug use. While awaiting trial, he was released on bail—but just four months later, in February 1979, he died of a heroin overdose, bringing the case and his tumultuous life to a grim end.

Guitar icon Jimi Hendrix was arrested in May 1969 at Toronto International Airport after Canadian customs agents discovered heroin and hashish in his luggage. Hendrix, who had no prior drug convictions, insisted the substances had been planted by a fan without his knowledge. The case cast a shadow over his Canadian tour, but in December of that year, a jury believed his defense and acquitted him of all charges. The incident, though brief, remains one of the most serious legal challenges Hendrix faced before his death the following year.

Rolling Stones frontman Mick Jagger was arrested in 1967 alongside bandmate Keith Richards after a police raid on Richards’s Redlands country estate uncovered amphetamines and cannabis. The raid, spurred by a tip reportedly planted by tabloid journalists, became a flashpoint in Britain’s counterculture clash. Jagger spent several nights in London’s Brixton Prison before being released on bail. Though he was initially convicted, the sentence was later overturned on appeal. The case galvanized public support, with even conservative outlets questioning the harsh treatment of the band.

In December 1988, the “Godfather of Soul” James Brown was sentenced to prison following a bizarre and dangerous run-in with the law. Months earlier, Brown had led police on a two-state, high-speed car chase that began in Augusta, Georgia, and ended in South Carolina. Authorities claimed Brown was under the influence of drugs during the pursuit. A jury convicted him of multiple charges including aggravated assault, weapons violations, and failure to stop for law enforcement. Brown served nearly three years in prison before being paroled in 1991.

In March 1976, David Bowie was arrested in Rochester, New York, on a felony marijuana possession charge. The rock star—then performing as his enigmatic “Thin White Duke” persona—was taken into custody along with fellow musician Iggy Pop and two others at a hotel following a concert. Though Bowie spent only a few hours in the Monroe County Jail before being released, the arrest made headlines. The charges were later dropped due to lack of evidence, but the mug shot remains one of the most iconic in rock history.