The Deep End is part of the successful and lucrative Diary of a Wimpy Kid franchise, which includes the original graphic novel series, a spin-off series, three animated film adaptations and a live-action film series, merchandise, and author appearances. Diary of a Wimpy Kid was created by the author and cartoonist Jeff Kinney (b. 1971) in 1998. It was first released as online entries for an adult audience 2005-2006 while Kinney worked to create the first novel. In 2006, Kinney signed a multi-book deal and the first book in the series, Diary of a Wimpy Kid, was published in 2007. At present, the Diary of a Wimpy Kid series runs to 19 titles with over 250 million copies of the books sold around the world. The series has a wide following and reach, and each new book rapidly rises into the bestseller charts on its release. The popularity of the Diary of a Wimpy Kid series has helped to shape the modern middle-grade genre, particularly graphic novels.

Kinney deliberately created Greg Heffley as an anti-hero: he is immoral, self-centered, and engages in delinquent behavior. This may partly be because Kinney originally intended to publish a comic strip-style book for the adult humor section, but was advised that his content would resonate better with the 8-12-year-old audience.