But it's their jail house photos that are, perhaps, their most infamous.
Lohan's booking photo was taken on July 20, after the actress mug shot).to begin a 90-day jail sentence handed down for violating her probation in a DUI case. Though she probably won't stay the full 90 days, she's already been in for more than the 84 minutes she spent in jail in 2006 (which resulted in another
Kardashian's mug shot also stemmed from a DUI-related probation violation. She turned herself into police on July 18, 2008, to begin serving a 30-day jail sentence. She only served three hours because of jail overcrowding.
Richie's booking photo comes from the four-day jail sentence she began on Aug. 23, 2007, which she received after being charged with driving under the influence in 2006. Her short jail sentence led to an even shorter stay - she was only behind bars for 82 minutes.
Hilton earned her mug shot after being sentenced to 45 days in jail for violating her probation stemming from a 2006 DUI charge. She turned herself in on June 3, 2007, after attending the MTV Movie Awards earlier that night. On June 7, she was reassigned to 40 days of home confinement with an electronic monitoring device, but was then sent back to jail the following day, as her sentence had specified no work release, home confinement or electronic monitoring. She was released on June 26.
Another thing these stars have in common is where they spent their hard time - the Century Regional Detention Facility in Lynwood, Calif.
So, who took the best booking photo?