Since the 2000s, the actress mostly appeared in dramatic independent films. A career highlight for Michelle Williams was starring in 2005's controversial movie Brokeback Mountain, about a homosexual relationship in the 1960s. One of its eight Academy Award nominations was a Best Supporting Actress nomination for Williams. Brokeback Mountain was followed with I'm Not There (2007), Synecdoche, New York (2008) and Martin Scorsese's Shutter Island (2010). Michelle Williams's performance as a drifter in 2008's Wendy and Lucy earned her critical praise and her work opposite Ryan Gosling in Blue Valentine (2010) led to the actress receiving another Academy Award nomination, this time for Best Actress. Upcoming films for Williams included playing Marilyn Monroe in My Week with Marilyn (2011) and the 2013 3-D Oz: The Great and Powerful.
Her relationship with actor and Brokeback Mountain co-star Heath Ledger remains the most high-profile of Michelle Williams's relationships since the 1990s. Before breaking up in 2007, they had one child together: a daughter named Matilda Rose, born October 28, 2005. After his death in January 2008, the media paid close attention to Michelle Williams's and her daughter; the two were also frequently followed by paparazzi.