1. Frank Sinatra (1938): A young Sinatra's 1938 mugshot – taken long before his rise to stardom – presented an unusually confident demeanor, not easily matched in the world of mugshots. Sinatra was arrested in Bergen County, New Jersey on charges of 'seduction' and 'adultery.' Although these allegations were later dismissed, the cool mugshot remains as part of Sinatra's intriguing legacy.

2. Janis Joplin (1969): The free-spirited singer, known for her bluesy vocal style, was arrested in Tampa, Florida, during a gig. The arrest came after Joplin allegedly used abusive language to police officers who were trying to control the crowd. The mugshot, capturing a cheeky grin, haunts her fans, who mourn the loss of such a spirited artist.

3. Jimi Hendrix (1969): This legendary guitarist wasn't rolling any stones when he was arrested at Toronto Airport for possession of narcotics. His mugshot highlighted an oddly calm and detached demeanour.

4. David Bowie (1976): Bowie's look in his '76 mugshot emulates his notorious 70's 'thin white duke' persona, with his quaffed hair and stylish look, even in a police station post-arrest. Bowie was charged for possession of marijuana in Rochester following a concert, though these charges were dropped.

5. Mick Jagger (1972): The Rolling Stones frontman is no stranger to controversy. Back in 1972, a mugshot was taken following his arrest in Rhode Island along with Keith Richards on charges of assault and obstruction of justice. His expression of nonchalant defiance in the photo reaffirms his rebellious rock-and-roll persona.

6. Nick Nolte (2002): Critically acclaimed actor Nick Nolte's 2002 mugshot showed a dishevelled and almost wild-eyed man. He was arrested in Malibu under the suspicion of intoxicated driving. The photograph remains one of the most memorable mugshots in history.

7. Paris Hilton (2007): Socialite Paris Hilton's mugshot of 2007, with her glamour still evident, was when she was placed on probation for alcohol-related reckless driving. Despite the grim situation, Hilton handled it with a hint of elegance.

8. Lindsay Lohan (2010): Once Hollywood’s darling, Lohan experienced a downfall accentuated by legal issues. Her 2010 mugshot, one of six altogether, was an emblem of this descent, filled with unfiltered sorrow.

9. Justin Bieber (2014): Pop star Justin Bieber's 2014 mugshot, taken in Miami on charges of DUI, painted a picture of a young man seemingly unperturbed by the gravity of his actions. His smile in the mugshot triggered mixed reactions from fans and critics.

10. Bill Cosby (2018): After being sentenced for sexual assault, Bill Cosby's mugshot portrayed a disgraced figure of the once beloved American comedian. His glazed look conveyed a stark disappearance of the character America once laughed with.