Michelle Williams’ Hollywood Evolution

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Love Lost

Williams and Spike Jonze, who directed Where the Wild Things Are, dated for a little over a year when they finally called it quits in Sept. 2009. Jonze was the first man Williams dated since former beau Heath Ledger's devastating death in Jan. 2008. "The timing was impossible," she told Vogue of her ill-fated relationship with Jonze. "I thought falling in love again was the only thing that was going to save me from the pain. This erroneous idea: It just makes things more complicated."

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Mommy And Me

Williams and daughter Matilda headed out to school on a rainy day in Brooklyn on Oct. 27, 2009.

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Not-So-Blue Valentine

Williams starred opposite Hollywood hunk Ryan Gosling in 2010's indie hit Blue Valentine, and the costars bonded by living together to prep for their roles as a married couple.

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A BFF Named Busy

Even though she's known both Michelle Williams and Jason Segel for years, Busy Philipps insists she didn't directly set the cute couple up. "People just made that up. I don't know how that happened," she told Anderson Cooper in January 2013. "The truth is, Jason Segel and I have been friends since we were on Freaks and Geeks together, and Michelle and I have been BFFs for 12 years or something like that. But it wasn't my doing. I guess I wish I could say it was."

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Red Carpet Stunner

Williams wowed on the red carpet with a beaded white Chanel Haute Couture gown at the 83rd Annual Academy Awards on Feb. 27, 2011. The actress was nominated for Best Actress for her lead role in Blue Valentine that year, though she ultimately lost out to Natalie Portman in Black Swan.

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Winning Smiles

Williams cozied up to her bestie in a stunning deep blue Jason Wu gown after her win for Best Actress at the 2012 Golden Globes for her turn as Marilyn Monroe. "I consider myself a mother first and an actress second, and so the person I most want to thank is my daughter, my little girl [Matilda Ledger], whose bravery and exuberance is the example I take with me in my work and in my life."

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Michelle as Marilyn

The slender actress had to gain weight and learn Marilyn Monroe's signature sultry walk for the part, but ultimately, Williams said transforming herself into the iconic actress "felt like being reborn. It felt like breaking my body and remaking it in her image, learning how she walked and talked and held her head."

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Williams Wins!

The three-time Oscar nominee scored the win for Best Female Lead for her stunning turn in My Week With Marilyn at the 2012 Film Independent Spirit Awards on Feb. 25, 2012.

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Romantic Rendezvous

Williams and longtime pal Segel first stepped out as more than just friends after a dinner in Brooklyn in March 2012. "They are smitten and very serious," a source told Luxury Handbag Shopping at the time.

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Family Time

Jason Segel joined Michelle Williams and her daughter Matilda, then 6, for a sunny day together at the Bronx Zoo on Aug. 31, 2012.

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Bikini Buds

Michelle Williams and boyfriend Jason Segel donned matching fedoras and shades while strolling along a beach in Cancun, Mexico on Jan. 2, 2013. Williams' BFF Busy Philipps, meanwhile, flaunted her own favorite accessory -- her growing baby bump -- in a hot red bikini.