Lindsay Lohan | Lindsay Lohan: 18 Highs and Lows | Photo 1 of 19 | EW.com

Jail sentence (2010)
The latest snag in what was once a young actress' promising career came when a teary Lohan was sentenced to 90 days in jail, starting July 20, for violating the terms of her probation. The ruling came at a time when the 24-year-old was arguably on the path to a comeback, following a few disappointing projects (more on those later). As a result, her work on the Linda Lovelace biopic Inferno and her participation in the promotion for Robert Rodriguez's Machete are — much like her possible return to glory — delayed. But just how did a teen movie queen end up jail-bound? For the answer, perhaps we need to start at the beginning

Lindsay Lohan | Lindsay Lohan: 18 Highs and Lows | Photo 1 of 19 | EW.com