Last Updated on May 6, 2025
The Diary of a Wimpy Kid series by Jeff Kinney has become a cultural phenomenon, captivating young readers with its humorous take on middle school life through the eyes of Greg Heffley. Combining witty narrative with cartoon-style illustrations, the books resonate with kids, parents, and educators alike. Since the first book’s release in 2007, the series has grown into a global bestseller, spawning movies, spin-offs, and a devoted fanbase. Below is a detailed look at the Diary of a Wimpy Kid books in order, from 1 to 20, including their publication dates, key plot points, and significance in the series.
1. Diary of a Wimpy Kid (April 1, 2007)
The book that started it all introduces Greg Heffley, a middle schooler navigating the perils of adolescence. Written as a journal (not a diary, as Greg insists), it chronicles his attempts to climb the social ladder, avoid bullies, and deal with his annoying older brother, Rodrick, and pesky younger brother, Manny. Key moments include Greg’s failed schemes, like starting a comic strip or joining the wrestling team, and his friendship with the loyal but uncool Rowley Jefferson. The book’s humor and relatable struggles set the tone for the series.
2. Rodrick Rules (February 1, 2008)
The second installment focuses on Greg’s strained relationship with his slacker older brother, Rodrick, who knows an embarrassing secret about Greg. Greg tries to survive Rodrick’s torment while juggling school pressures, like dodging swim team and navigating crushes. A highlight is Rodrick’s band, Löded Diper, which becomes a recurring element. The book deepens the Heffley family dynamic and showcases Greg’s flawed but endearing personality.
3. The Last Straw (January 13, 2009)
Greg’s dad, Frank, takes center stage as he pushes Greg to toughen up through sports and chores, much to Greg’s dismay. From failed soccer practices to Greg’s attempts to impress his crush, Holly Hills, the book is packed with hilarious misadventures. The introduction of the “Spag Union” military school threat adds stakes, while Greg’s schemes to avoid responsibility highlight his knack for creative excuses.
4. Dog Days (October 12, 2009)
Summer vacation sounds great, but for Greg, it’s a series of disappointments. From a failed comic strip job to a disastrous attempt at starting a lawn-mowing business, Greg’s summer spirals. The addition of a family dog, Sweetie, brings chaos, and Greg’s obsession with video games clashes with his dad’s expectations. The book’s lighter tone and summer setting make it a fan favorite.
5. The Ugly Truth (November 9, 2010)
Greg faces new challenges as he and Rowley drift apart after a fight. Navigating middle school without his best friend, Greg tries joining new social circles and deals with awkward moments like dental visits and puberty talks. The book introduces Uncle Gary, whose wedding adds humor, and explores themes of growing up and changing friendships, making it a pivotal entry.
6. Cabin Fever (November 15, 2011)
Winter brings trouble when Greg gets snowed in and faces consequences for a school vandalism incident. His paranoia about getting caught drives the plot, alongside holiday chaos with the Heffleys. The book’s cozy yet tense atmosphere, paired with Greg’s moral dilemmas, offers a fresh spin. It also delves into Manny’s growing mischief, setting up future conflicts.
7. The Third Wheel (November 13, 2012)
Love is in the air as Greg hunts for a date to the Valentine’s Day dance. His pursuit of girls, including Holly Hills, leads to cringe-worthy moments, while Rowley’s unexpected romance adds drama. Greg’s reflections on his “third wheel” status and flashbacks to his childhood bring depth. The book’s focus on romance and social dynamics resonates with older readers.
8. Hard Luck (November 5, 2013)
Greg’s luck seems to run dry after another falling-out with Rowley. Desperate for popularity, he turns to a Magic 8 Ball for guidance, leading to absurd decisions. The introduction of Fregley as a quirky ally and the Heffley family’s Easter antics keep the laughs coming. The book explores Greg’s struggle to find his place, with a bittersweet tone.
9. The Long Haul (November 4, 2014)
The Heffleys hit the road for a disastrous family vacation. From a runaway pig to a chaotic motel stay, Greg’s journal details every mishap. The book’s road trip format offers a change of pace, with new characters like the Beardo family adding humor. It’s a standout for its slapstick comedy and was adapted into a 2017 film.
10. Old School (November 3, 2015)
Greg’s town goes tech-free for a week, forcing him to confront a world without gadgets. Meanwhile, his dad’s push for a “real” childhood lands Greg at a rustic summer camp. The book pokes fun at nostalgia while delivering classic Greg antics, like dodging camp chores and navigating school elections. It’s a commentary on modern life with plenty of laughs.
11. Double Down (November 1, 2016)
Greg dreams of fame by making a horror movie with Rowley, but their low-budget project flops. Meanwhile, he obsesses over video games and faces pressure to join the school band. The book’s gaming references and creative schemes, like Greg’s candy-selling hustle, appeal to fans. It also highlights his ongoing rivalry with Manny.
12. The Getaway (November 7, 2017)
The Heffleys escape winter for a tropical resort vacation, but paradise turns chaotic with sunburns, wildlife encounters, and resort mishaps. Greg’s attempts to enjoy the trip while dodging family drama fuel the humor. The exotic setting and travel disasters make this a refreshing entry, with a nod to cultural misunderstandings.
13. The Meltdown (October 30, 2018)
A massive snowstorm turns Greg’s neighborhood into a battleground for epic snowball fights. At school, Greg navigates social cliques and winter woes, while the Heffley household descends into chaos. The book’s action-packed sequences and winter setting evoke nostalgia, with Greg’s strategic scheming taking center stage.
14. Wrecking Ball (November 5, 2019)
The Heffleys inherit money and decide to renovate their house, leading to construction disasters. Greg deals with the upheaval while facing school pressures and a surprise move looming. The book introduces new challenges, like Greg’s fear of change, and includes memorable moments like a chaotic home demolition. It’s a turning point for the series.
15. The Deep End (October 27, 2020)
The Heffleys go camping to save money, but their RV adventure is anything but relaxing. From a crowded campground to river rafting mishaps, Greg’s journal captures the chaos. The book’s outdoor setting and survival humor shine, with Greg’s attempts to impress other campers adding charm. It’s a return to classic Wimpy Kid antics.
16. Big Shot (October 26, 2021)
Greg tries his hand at basketball, despite his lack of athletic talent. His team’s losing streak and his dad’s coaching ambitions create tension, while school rivalries heat up. The book’s sports theme and underdog story appeal to readers, with Greg’s self-awareness adding depth. It’s a fun exploration of perseverance.
17. Diper Överlöde (October 25, 2022)
Rodrick and his band, Löded Diper, take the spotlight as Greg gets roped into their quest for rock stardom. From shady gigs to band drama, Greg chronicles their misadventures. The book dives into Rodrick’s world, offering fans a fresh perspective. Its music-centric plot and sibling dynamic make it a standout.
18. No Brainer (October 24, 2023)
Greg’s school faces budget cuts, threatening to shut down. He gets involved in saving it, but his fundraising ideas—like a school casino—go awry. The book tackles real-world issues like school funding with humor, while Greg’s schemes and social struggles keep it grounded. It’s a timely addition to the series.
19. Hot Mess (October 22, 2024)
Greg joins a foreign exchange program, leading to a chaotic stay with a host family. Cultural clashes and school challenges test his patience, while the Heffleys’ home life remains turbulent. The book’s global perspective and fresh setting offer new humor, with Greg’s adaptability (or lack thereof) driving the plot.
20. Book 20 (Expected Late 2025, Title TBD)
As of May 2025, the 20th book has not been officially released, but Jeff Kinney typically follows an annual release schedule. While details are scarce, fans expect another chapter of Greg’s middle school journey, likely tackling new themes relevant to young readers. Based on Kinney’s pattern, it will blend humor, relatable struggles, and cartoon illustrations. Check x.ai or official Diary of a Wimpy Kid channels for updates on the title and release date.
Why the Series Endures
The Diary of a Wimpy Kid series thrives on its universal appeal. Greg’s flawed, self-centered perspective mirrors the awkwardness of youth, while the humor—rooted in family dynamics, school drama, and failed schemes—transcends generations. Kinney’s simple yet expressive illustrations enhance the storytelling, making the books accessible to reluctant readers. Each entry builds on the Heffley family’s world while introducing fresh settings, from road trips to tropical resorts, keeping the series dynamic.
Accessing the Books
The Diary of a Wimpy Kid books are available in hardcover, paperback, e-book, and audiobook formats through major retailers like Amazon, Barnes & Noble, and local bookstores. Libraries often carry the series, and digital versions can be found on platforms like Kindle or Apple Books. For the latest updates on new releases, visit wimpykid.com or follow Jeff Kinney on social media platforms like X.
Final Thoughts
From Greg’s first journal in 2007 to the anticipated 20th book in 2025, the Diary of a Wimpy Kid series remains a beloved staple for young readers. Its blend of humor, heart, and honesty captures the messy reality of growing up. Whether you’re a longtime fan or new to the series, diving into Greg Heffley’s world is a guaranteed laugh. Pick up the books in order and join the millions who’ve laughed at Greg’s wimpy but unforgettable adventures.