Further success came with her roles as John McClane's daughter in Live Free or Die Hard (2007) and Ramona Flowers in Scott Pilgrim vs. the World (2010).

Her critically acclaimed performance as an alcoholic struggling with sobriety in the drama Smashed (2012) was followed by a series of roles in other independent films, including The Beauty Inside (2012), The Spectacular Now (2013), Faults (2014), Alex of Venice (2014), and Swiss Army Man (2016).

Her other roles include the comedy-drama All About Nina (2018), the action film Gemini Man (2019), the Huntress in Birds of Prey (2020), and Hera Syndulla in the Star Wars series Ahsoka (2023).

[9] After her brief performance in that show, Winstead began making appearances in various television series and earned guest roles in Touched by an Angel and Promised Land.

She was offered a role in the film A Cinderella Story, but turned it down as she had just graduated from school and was going on a cruise with friends (where she met Riley Stearns, her future husband).

She starred in the 2006 horror movie Final Destination 3 (which Wong directed and Morgan produced) as lead character Wendy Christensen,[15] the "beleaguered heroine who experiences the premonition" that sets the story in motion.

[17] Winstead's performance fared positively with reviewers;[18] James Berardinelli stated she "does as competent a job as one could expect in these dire circumstances,"[19] while Felix Gonzalez, Jr found her "likeable" in her role.

[22] A moderate box office success in selected theaters, Bobby received mixed reviews[23] with many criticisms directed at the film's script.

Quentin Tarantino cast her as a well-intentioned but vapid and naïve actress in Death Proof, his high-speed segment of the double–feature exploitation horror Grindhouse.

The production under-performed commercially but attracted significant media buzz and critical acclaim,[27][28] Variety magazine noted that Death Proof "proves its worth as a stand-alone feature" and found Winstead's "emergence" to be "one agreeable plus [to the movie]".

[29][30] Her next film appearance of the year was opposite Bruce Willis in Live Free or Die Hard,[3] portraying John McClane's estranged daughter, Lucy.

[41] Winstead was cast as the lead female in the 2011 prequel film to 1982's The Thing,[42][43] which followed a group of scientists who discover an alien buried deep in the ice of Antarctica, realizing too late that it is still alive.

[46][47] Critics singled out Winstead for praise in her performance,[48] with Las Vegas Weekly asserting that she "makes for an appealing protagonist, and Kate is portrayed as competent without being thrust into some unlikely action-hero role".

[64][65] Winstead was also cast in Roman Coppola's A Glimpse Inside the Mind of Charles Swan III (2013), as Kate, "the best friend of [Charlie Sheen's] girlfriend who just broke up with him.

Winstead next co-starred with Adam Scott, Richard Jenkins, Jane Lynch, Jessica Alba, Amy Poehler, and Catherine O'Hara in A.C.O.D.

"[69] Screen Rant critic Ben Kendrick wrote: "[Winstead] and [Alba] also deliver in their contributions – though both of their characters are mainly designed to be mirrors for Carter to examine his own life and choices.

Alex's gradual metamorphosis into a richer, more fully realized young woman is accomplished in hundreds of tiny emotional brushstrokes, flitting across her girl-next-door wholesomeness in ever-shifting patterns".

While her resume up 'til now is a mix of blockbusters (Final Destination 3, Live Free or Die Hard) and indie favorites (Scott Pilgrim vs. the World), this will change as she continues to grow into her profoundly blossoming career.

As Alex, she always wears a look of determination, even when she's exhausted and losing the new battles thrown at her: learning how to be alone, taking care of her family and keeping the job she's worked her entire life for.

Winstead headlined the psychological thriller 10 Cloverfield Lane,[100] appearing as Michelle, a woman held in a shelter with two men, who claim the outside world is affected by a widespread chemical attack.

The film, directed by Dan Trachtenberg,[101] was released on March 11, 2016, to a widely positive reception from critics who, according to website Rotten Tomatoes, agreed that the movie "makes the most of its confined setting and outstanding cast".

[102] Daily Express found Winstead "sympathetic" and remarked that she "creates a character who is smart and resourceful",[103] while writer James Berardinelli called her a "good choice" to play the heroine as she is "strong yet feminine".

The film, co-starring Daniel Radcliffe and Paul Dano, follows a hopeless man stranded on an island who befriends an apparent dead body as he tries to get back home.

[108] Winstead also had a role in John Krasinski's small-scale dramedy The Hollars, opposite Richard Jenkins, Anna Kendrick, Mary Kay Place, and Margo Martindale.

[109] She played the ex-girlfriend of Krasinski's struggling New York City graphic novelist, who returns to his hometown after learning his mother has fallen ill.[110] Like Swiss Army Man, the production was screened at Sundance and received a limited U.S. theatrical release in August 2016.

[112] The series received mildly positive reviews by critics,[113][114] with New York Magazine calling Winstead's casting the "smartest decision the makers made",[115] and The A.V.

[119] Winstead starred opposite Ewan McGregor in the third season of Fargo as Nikki Swango, "a crafty and alluring recent parolee with a passion for competitive bridge playing with a plan, focused on always being at least one move ahead of her opponents".

[120][121][122] The season is set around December 2010 in Minnesota and follows the lives of McGregor and Winstead's criminal couple roles; it premiered on April 19, 2017,[123] to positive reviews.

[132] In late-September 2018, Winstead was announced to play Huntress in Warner Bros.' DC Comics film Birds of Prey (And the Fantabulous Emancipation of One Harley Quinn).

The Man released the single and video for "Noise Pollution (Version A, Vocal Up Mix 1.3)" from their album Woodstock, featuring Winstead and Zoe Manville.