Typically you hear about people trying to escape from jail, not looking to prolong their stay. But that happens more often than you think. For some, it’s no doubt due to the comfy bunk beds, four-star meals, and free gym membership. But whatever the inmates’ reasons are — and a few are pretty strange — some just can’t get enough of life behind bars.
Lindsay Lohan | 2010
In July 2010, following one of her numerous arrests, the then 24-year-old actress was found guilty for violating her probation and was sentenced to 90 days in the slammer. But in Hollywood, celebrities are often spared from jail time because they are delicate magical creatures who cannot be caged, and so Lohan spent only 14 days in jail. So maybe that’s why, when she was allowed to leave, Lohan wasn’t in a big hurry; instead of getting out of there ASAP, she waited for her stylists to show up so they could ensure she’d look her best for the throngs of paparazzi eagerly awaiting her release. The walk from the jail to her waiting car lasted about 30 seconds.