Alison Pill made her first mainstream appearance in 1997 in the "Moving Parts" episode of the mystery fantasy television series ‘The New Ghostwriter Mysteries.’ She then appeared in television films and series, such as ‘Psi Factor: Chronicles of the Paranormal’ (1998), ‘The Last Don II’ (1998), ‘Stranger in Town’ (1998), and ‘God's New Plan’ (1999), before making her big-screen debut in the 1999 Canadian film ‘The Life Before This’ directed by Jerry Ciccoritti. That same year, she also starred as ‘Shapiro / Marfa’ in the television film ‘Jacob Two Two Meets the Hooded Fang’ directed by George Bloomfield. The film was an adaptation of Mordecai Richler’s novel of the same name. Alison next appeared in ‘Skipped Parts’ (2000), ‘Perfect Pie’ (2002), ‘Pieces of April’ (2003), ‘Confessions of a Teenage Drama Queen’ (2004), and ‘Dan in Real Life’ (2007).
In 2008, she portrayed ‘Anne Kronenberg’ in the American biographical film ‘Milk’ directed by Gus Van Sant. The film received universal acclaim upon release and was a financial success. She was next seen in the 2010 romantic action comedy film ‘Scott Pilgrim vs. the World’ where she played the role of Kimberly "Kim" Pine. While the film saw positive reviews upon release, it failed to achieve success at the box office. Nevertheless, it developed a cult following in the subsequent years. The following year, she starred as ‘Zelda Fitzgerald’ in the fantasy comedy film ‘Midnight in Paris’ directed by Woody Allen. The film earned critical acclaim with critics praising its humor and direction. ‘Midnight in Paris’ was also a massive box office success, grossing over $154.1 million against a budget of $17 million.
Alison then starred in films like ‘Goon’ (2011), ‘To Rome with Love’ (2012), ‘Snowpiercer’ (2013), ‘Cooties’ (2014), ‘Zoom’ (2015), ‘Hail, Caesar!’ (2016), ‘Goon: Last of the Enforcers’ (2017), ‘Ideal Home’ (2018), ‘Vice’ (2018). She was last seen in the 2021 Canadian drama film ‘All My Puny Sorrows’ directed by Michael McGowan. The film had its premiere at the Toronto International Film Festival and garnered positive reviews upon release.