Kinney spent 8 years working on the book before showing it to a publisher. In 2004, FunBrain and Kinney released an online version of Diary of a Wimpy Kid. The website made daily entries from September 2004 to June 2005. The online version had received almost 20 million views by 2009. Nonetheless, many online readers requested a printed version. In February 2006, during the New York Comic Con, Kinney signed a multi-book deal with publisher Abrams Books to turn Diary of a Wimpy Kid into a printed book series. The first installment was released in April 2007 and received immediate success. In April 2009, Time magazine named Kinney in the Time 100 most influential people.
Jeff Kinney announced that a film based on the first book would be produced by 20th Century Fox. The film was released on March 19, 2010, moved up from an April 2 release date. It was directed by Thor Freudenthal, who also directed Hotel for Dogs. The film starred Zachary Gordon as Greg, Robert Capron as Rowley (Greg's best friend), Steve Zahn as Frank (Greg's father), Rachael Harris as Susan (Greg's mother), Devon Bostick as Rodrick (Greg's older brother), Connor and Owen Fielding as Manny (Greg's younger brother), Chloë Grace Moretz as a new character named Angie, and Grayson Russell as Fregley.
Diary of a Wimpy Kid was well received from The Princeton Review, Gold Card Association, The Dallas News, The TRR Editors, The NW Press, and The JJ Printing Company. The New York Times, which ranks children's serials collectively on a "Series Books" bestseller list, has included the Wimpy Kid series for 664 weeks as of December 8, 2021. USA Today, which ranks best sellers based on sales alone regardless of genre or intended audience, has listed Diary of a Wimpy Kid in its top 150, peaking at number 8, for 141 weeks as of April 4, 2010.
There is a second film in the Diary of a Wimpy Kid film series that was released on March 25, 2011, which was based on the second book Rodrick Rules, with Zachary Gordon returning as Greg Heffley. Diary of a Wimpy Kid: Rodrick Rules was also filmed in Vancouver, BC, Canada. The film also contains some scenes from The Last Straw.
The third film combines the third and fourth books The Last Straw and Dog Days, taking stories from both, but mainly from Dog Days, from which it took its title. The decision to blend the two films was made to keep up with the ages of the actors. The film was released on August 3, 2012.
A musical titled Diary of a Wimpy Kid: The Musical was produced by the Children's Theatre Company in 2016.
The likelihood of a fourth live-action film was slim. Kinney has announced the possibility for an animated film to be based on Diary of a Wimpy Kid: Cabin Fever as the next installment. In an interview for the book Hard Luck, Jeff Kinney stated he was working with Fox on a half-hour special of Cabin Fever, which was to be aired in late 2014, but as of 2021 no updates on the special have been announced. In September 2016, Jeff Kinney announced officially the production of a fourth film, Diary of a Wimpy Kid: The Long Haul, on his Twitter account. The film was released in May 2017 and was based on The Long Haul, Hard Luck, and The Third Wheel. On August 6, 2019, Disney announced they would reboot Diary of a Wimpy Kid, Home Alone and Night at the Museum for their streaming service, Disney+.
Audiobooks have been released for each main installment in the Diary of a Wimpy Kid series. The Recorded Books versions are read by Ramon de Ocampo, while the Penguin Books versions are read by Dan Russell, who has done so since The Third Wheel, and in 2018 he re-narrated the first 6 books for the markets where Penguin publish the series.
A spin-off series has been published, written from Rowley's perspective. The first installment, Diary of an Awesome Friendly Kid: Rowley Jefferson's Journal, was released on April 9, 2019, and is a series of anecdotes about Greg and Rowley's friendship. The second, Rowley Jefferson's Awesome Friendly Adventure, is in the style of a fantasy adventure and was released on August 4, 2020. The book's original release date was April 7, 2020, but was delayed due to the COVID-19 pandemic. The third, Rowley Jefferson's Awesome Friendly Spooky Stories, was released on March 16, 2021.
On December 10, 2020, Disney announced at their 2020 Investor's Day that an animated Diary of a Wimpy Kid film would be coming to Disney+ on December 3, 2021.
Sixteen books in the series have been released as of 2021, and a 17th book is due to be released in October 2022 (Diper Överlöde); an activity book has also been released. A spin-off series, centering on the character Rowley Jefferson, has three installments as of 2021. The first, second, fourth and ninth installments have been adapted into films by 20th Century Fox; two books have been released chronicling the production of the films.