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Following early work as a television director, most notably for The Famous Jett Jackson, Levy gained recognition in the 2000s for directing comedy films such as Big Fat Liar (2002), Just Married (2003), Cheaper by the Dozen (2003), and The Pink Panther (2006). He then found further success as the director of the first three films in the Night at the Museum film franchise (2006–14). In the early 2010s, he directed films including Date Night (2010), Real Steel (2011), and The Internship (2013), developed several comedy television pilots, and executive produced the first five seasons of the ABC sitcom Last Man Standing. Levy was a producer on the 2016 sci-fi film Arrival, which earned him an Academy Award nomination for Best Picture.

Levy was an executive producer through the entire run of the Netflix original series Stranger Things. He directed the third and fourth episodes of each of the show's first four seasons, as well as the sixth and seventh episodes of the final season. He also directed the Netflix limited series All the Light We Cannot See (2023). Levy has collaborated with Ryan Reynolds by directing Free Guy (2021), The Adam Project (2022), and Deadpool & Wolverine (2024), with the latter emerging as his highest-grossing film and the highest-grossing R-rated film of all time.