Current age: 27
Career at 20: Just My Luck and A Prairie Home Companion, which costarred Meryl Streep, were released in the months before Lindsay's 20th birthday, and next came Bobby in November 2006 and Georgia Rule in May 2007.
Relationship status at 20: Lindsay went through a few personal struggles in 2006 and 2007, including a DUI arrest and a rehab stint. During that time, she and Hard Rock Cafe heir Harry Morton broke up, and in May 2007, she was linked to Calum Best, a British TV personality.
Quoted at 20: For Lindsay's August 2006 Elle interview, the actress talked about all her tabloid coverage. "You kind of ask for it when you go to nightclubs," she said. "People are like, 'Just don't go out!' but I can't help it. I literally come out of my hotel and the [photographers] are there. It's not like I ask them to follow me. But you know, it's actually weird when the paparazzi's not there and things aren't being written, because you kind of wonder, 'Do people not care anymore?'"