In 2008, Winstead screen-tested for the role of Wonder Woman in the film adaption of Justice League. She starred in a lead role in Make It Happen, a dance film. The film went straight to DVD in the US, and gained a small collection in the UK, which eventually led to its financial failure. Nevertheless, the film proved a delight for Winstead to shoot, as she had always dreamed about becoming a dancer.
Winstead co-starred opposite Michael Cera in the comic-book adaptation Scott Pilgrim vs. The World, under the direction of Edgar Wright. Filming occurred from March to August 2009 and was released in 2010 to critical acclaim but lackluster box office returns.
On February 2010, Winstead landed the lead role in the prequel to The Thing, which is directed by Matthijs van Heijningen Jr. and tentatively set for an April 29, 2011 release.
Winstead has expressed interest in returning as Lucy McClane for the fifth installment of the Die Hard film series, although her involvement in the project is yet to be confirmed.She was also mentioned in news regarding the prequel to The Ring (tentatively titled The Ring 3D), though further information is yet unknown.
In 2010, Winstead reportedly tested for the female lead in a romantic comedy penned by Elan Mastai named The F-Word opposite Casey Affleck, but no decision has been made as of November. She was also tested to be the female lead in the Spider-Man reboot and the lead opposite Matt Damon in We Bought a Zoo, a film adaptation of Benjamin Mee's autobiographical novel of the same name, although she was not chosen in either case.