Michelle Williams: Jen Lindley
Although Jen Lindley dies of a fatal heart condition in the series finale, Michelle Williams, 32, is arguably the most successful of the former Capeside crew — career-wise, anyway.
After receiving a Best Supporting Actress Oscar nomination in 2005 for Brokeback Mountain, Michelle appeared in a string of serious, critically acclaimed movies including Synecdoche, New York, Blue Valentine (cue her second Oscar nom), and Shutter Island. Last year she got rave reviews for her star turn as the iconic Marilyn Monroe in My Week With Marilyn, and she’s sure to dazzle as Glinda in 2013’s Oz: The Great and Powerful.
Michelle started dating her Brokeback co-star Heath Ledger in June 2004, and the couple had a daughter, Matilda, on October 28, 2005. In a tragic twist, Heath died of a prescription drug overdose on January 22, 2008, only a few months after he and Michelle called it quits. In an interview in the October 2011 issue of Vogue, Michelle revealed, “For a really long time, I couldn’t stop touching people’s faces. I was like, ‘Look at you. You move. You’re here.’ It all just seemed so fleeting, and I wanted to hold on to it.”
In the wake of Heath’s death, Michelle has developed a thing for guys behind the camera (translation: guys just like Dawson!): After dating director Spike Jonze from 2008 to 2009, Michelle had a rumored fling with Jane Eyre director Cary Fukunaga in early 2011. She's currently dating How I Met Your Mother star Jason Segel.
There’s always been a lot of “City Girl” Jen in Michelle — emotional pain included. Fortunately, Michelle hasn’t let it bring her down. At all.