[3] Following early work as a television director, Levy gained recognition in the 2000s for directing comedy films like Big Fat Liar (2002), Just Married (2003), Cheaper by the Dozen (2003) and The Pink Panther (2006).

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 ABC sitcom Last Man Standing.

Levy has recently 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.

While studying performing arts, he made his acting debut in Zombie Nightmare (1987), a low-budget horror film in which he portrayed the character Jim Bratten, the leader of a group of teenagers.

Outside of 20th Century Fox, Levy worked to expand 21 Laps' range outside of primarily family-friendly comedies;[15] this included producing the A24 drama The Spectacular Now (2013), the ensemble dramedy This Is Where I Leave You (2014), and the Academy Award-winning sci-fi film Arrival (2016).

[12] In 2021, Levy produced the film adaptation of the slasher novel There's Someone Inside Your House by Stephanie Perkins under his 21 Laps Entertainment label, alongside James Wan's Atomic Monster studio for Netflix.

[22] In November 2022, Levy entered talks to direct a Star Wars movie for Lucasfilm following the conclusion of his work on Deadpool & Wolverine and the fifth and final season of Stranger Things.

[27] In July 2002, it was reported that Levy would direct the film adaptation of the comic strip Zits for Universal Pictures, with Adam 'Tex' Davis hired to write the screenplay.

[32] On January 16, 2003, it was announced that Levy would direct the sports film Overtime, written by Sheldon Turner, for Warner Bros. Pictures, and would reunite with his Just Married star Ashton Kutcher on the project.

[40] Also on November 27, 2006, it was reported that Levy's 21 Laps Entertainment had signed a deal with 20th Century Fox to produce the original comedy drama Father Figure, written by Mark Friedman.

[41] In addition to The Talent Thief and Father Figure, 21 Laps Entertainment reportedly set up a Fox network deal for the pilot script The Institution, a single-camera half-hour series from Levy and Chris Moynihan that focuses on three couples as they weather the highs and lows of matrimony.

[55] On April 16, 2007, it was announced that Levy would direct and produce the fantasy film The Seems for 20th Century Fox, based on the novel by John Hulme and Michael Wexler, who would also write the screenplay for the project.

[56] On April 30, 2007, it was announced Levy would direct the coming-of-age comedy-drama The Way Back, written by Jim Rash and Nat Faxon, for Fox Searchlight Pictures, with production expected to begin in mid-June.

[64][65] On January 22, 2009, it was reported that Levy would produce the film adaptation of Alec Greven's book How to Talk to Girls for 20th Century Fox, and would develop the project as a potential directing vehicle.

[67] On September 16, 2010, it was announced that Levy would produce a feature film based on the Spike TV television series Deadliest Warrior for Paramount Pictures, and was also eyeing the project as a potential directing vehicle.

[69][70] In February 2012, Levy told Collider that a script had just been turned in to Paramount, and that he would likely only serve as producer, though he also expressed hope that the film could enter production that year.

[67] On February 3, 2011, it was announced that 20th Century Fox had acquired an original action adventure pitch by Carlton Cuse for Hugh Jackman to star and Levy to produce and direct.

[73] On June 7, 2011, it was announced that Tom McCarthy would rewrite the screenplay for Home Movies, a supernatural comedy drama being produced by Levy's 21 Laps Entertainment for DreamWorks Pictures, from initial drafts by Jared Stern.

[75] In February 2012, during an interview with Collider, Levy described the project as being more difficult to move forward due to complexities surrounding casting, scripting, and its larger budget.

[80] On February 24, 2012, Levy confirmed he had been interested in two years prior, and had discussed the project with original producer Albert S. Ruddy with plans to cast Stiller and Owen Wilson, but that it was not something he was now involved in.

[88] In September 2018, Jonathan Krisel signed on to direct the film, with Chris Galletta set to write the screenplay from a previous draft by Mike Rosolio.

[102] On November 14, 2013, it was announced that Levy would direct the adventure film City That Sailed for 20th Century Fox, with Audrey Wells writing the screenplay and Will Smith starring.

[104] On October 16, 2014, it was announced that Levy would direct Minecraft, a film adaptation of the video game by Mojang Studios, for Warner Bros. Pictures, with Roy Lee and Jill Messick producing.

[101] On July 22, 2015, it was announced that 20th Century Fox had set Carter Blanchard to adapt the Brandon Sanderson 2013 novel Steelheart, the first installment in The Reckoners series, as a potential directing vehicle for Levy.

[110] On October 25, 2016, it was announced that Levy would direct the action adventure film Uncharted, based on the video game series of the same name, for Sony Pictures, with Joe Carnahan writing the most recent draft of the screenplay.

[120] On November 8, 2017, it was announced that Crater, a science fiction spec script by John Griffin, had been acquired by 20th Century Fox and that Levy was in negotiations to direct and produce the project.

[121] On January 12, 2021, it was announced that Kyle Patrick Alvarez would direct the project instead, with Levy only serving as a producer, with the film moving to a Disney+ release after the acquisition of 21st Century Fox by Disney.

[125] On January 13, 2022, it was announced that a series adaptation of Real Steel was in the early stages of development at Disney+, with Levy serving as executive producer alongside Robert Zemeckis, Jack Rapke, Jacqueline Levine, Susan Montford and Don Murphy.

[126] On August 14, 2021, following the successful first-day box-office gross of Free Guy, star Ryan Reynolds confirmed that Disney wanted to make a sequel.

[130] In February 2023, it was announced Levy would produce the comedy Boy Band for Paramount Pictures alongside Ryan Reynolds, who would also co-write and star in the project.