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Multiple Versions:

  • Approval of God: Devon Bostick (the actor who played Rodrick for the first three films) was amused by the usage of Manny as a meme to promote the Black Lives Matter Movement in 2020.
  • Creator's Favorite: Rowley is Jeff Kinney's favorite character. He's one of the few characters to appear in every book, and has a series of Spin-Off books.
  • Defictionalization: The idea of the "Cheese Touch" caught on with several schoolchildren who had read the books or seen the movies, and they would partake in that game in day-to-day life (even if there wasn't any old cheese around from which to get the Cheese Touch). It wasn't treated with the same weight as it was in the books, though, and was often treated more like a game of Tag. If you grew up in the late 2000s or early 2010s, there was probably a period of time where you had to constantly cross your fingers for fear of getting "cheese-touched".
  • Development Hell: In late 2012, it was announced that an animated 30-minute TV special of Cabin Fever was in production, and set to be released in late 2014. It was shelved and replaced by a live-action adaption of The Long Haul some time later. Animated adaptations of the books would finally come to fruition with the first two books released in 2021 and 2022 respectively on Disney+, and the long-awaited Cabin Fever was finally released in 2023.
  • Follow the Leader:
    • The amount of book series that started popping up after Wimpy Kid came out that were all based on middle schoolers' journal entries combining words and drawings was definitely not a coincidence. Especially with Diary of a Wimpy/(synonym for that) _____ as their title. Notable examples include Dork Diaries and Zombie Kid Diaries.
    • The CGI animated film may well be going for the 2D-imitating style of CGI animation popularized by The Peanuts Movie and Captain Underpants: The First Epic Movie.
  • Keep Circulating the Tapes: The original webcomic was removed from Funbrain.com in August 2021, but can be viewed on the Internet Archive.
  • Technology Marches On:
    • In the webcomic, Manny breaks Greg's Walkman by stuffing a cookie in the cassette slot. The novel changed it to a generic video game system, while in the film it was an Xbox 360.
    • Game Boys with link cables appeared in the webcomic, which were outdated by about 7 years when the first print book was published.
    • In the webcomic, Rowley owns a PlayStation. In the film, he owns a Wii.
    • When the first book was published as a webcomic in 2005 and eventually published as a physical copy in 2007, social media had little or no existence in real life. After 2010 and social media grew in popularity, some of the Wimpy Kid books mention social media.
    • The Heffley family still uses a landline cordless telephone, even after the smartphones' popularity in the early to mid 2010s.
    • As smartphones and tablets became commonplace in the early to mid-2010s, most of the Wimpy Kid books from that era began having characters use smartphones and tablets. For instance, at one point in The Getawaynote , Greg mentions having an electronic device and there’s a drawing of him holding what looks like either a smartphone or an iPod.
    • As for the Heffley's TV sets, some books have the Heffleys owning a box-shaped CRT TV. Later, they upgrade to a newer LCD flatscreen TV.
    • At one point, Greg has a desktop computer in Double Down - while desktop computers are still used, Double Down implies it's Greg's.
    • Rodrick Rules:
      • Susan accidentally ruins the tape she recorded of Rodrick's band performing by making comments throughout the video. In The New '10s, modern commercially-available video-editing software such as Adobe Premiere would be able to fix that problem. On the other hand, it's entirely possible that no one among the cast would know that, much less know how to video-edit. Even if they did, they probably wouldn't want to shell out for an expensive software like that just because of that one hiccup.
      • Greg isn't able to finish his history paper when the power goes out on the family's desktop computer, while a laptop computer wouldn't need to be connected to power to continue running.note 
  • What Could Have Been:
    • Lucas Cruikshank of Fred fame was originally cast to play the role of Greg, but was deemed too old to fit at age 16, and was voluntarily replaced by Zachary Gordon.
    • According to this, Jeff originally intended the books to be a 5-part series, mentioning that the first three books were based on the FunBrain version and Dog Days's plot base. However, this was untrue as Jeff wrote a sixth book (that being Cabin Fever) and still does to this day.
    • As mentioned above, a Cabin Fever animated short was in production in the early 2010's, only for it to be shelved. Fortunately, an adaptation of said book (Diary of a Wimpy Kid Christmas: Cabin Fever) was released in December 2023, following the success of the first two Disney+ films.
    • Steve Zahn and Rachael Harris were approached to reprise their roles as Frank and Susan Heffley for The Long Haul, unlike many of the already grown-up child actors. However, Zahn turned down the offer due to his lack of interest in returning to the franchise without the original cast and his scheduling commitments to War for the Planet of the Apes, while Harris turned it down due to scheduling commitments to Lucifer.
    • Kinney's early sketches seen in The Wimpy Kid Movie Diary show that Manny was once named "Vermin."
  • The following scenes from the webcomic have yet to occur (or at least have an equivalent) in the books:
    • Greg mentions that by writing in his diary, he gets out of one chore; he chooses cleaning toilets, which goes to Rodrick.
    • Greg watches a movie with his father and Rodrick; his mother catches them watching it during a racy scene and makes them feel ashamed, to which Greg responds by pretending to also be disgusted.
    • Greg writes the wrong answers on a test to trick a classmate into doing so, then erases them and replaces them with the right answers; the classmate gets detention.
    • Rodrick has "#1" slips in his junk drawer, which he uses to impress girls when they ask him for his number. He also has a book called "Dumb Animals", which Greg uses as a source for his moose assignment.
    • Greg's mother removes the prize from specially marked cereal boxes due to causing friction between him and Rodrick; however, Rodrick gets lucky with the cereal, which Greg is okay with due to having once gotten sick from eating all the marshmallows from a cereal box.
    • Greg mentions a home video of when he was successfully toilet-trained, which Rodrick likes to hold over his head.
    • Greg pretends to believe in Santa due to Rodrick getting fewer presents for saying he doesn't; he stops when he walks in on his parents wrapping the "Santa" presents.
    • Rodrick gets a model rocket which he builds, then launches; Greg finds it, but ends up accidentally breaking it, then claiming he found it that way. Earlier, Rowley gets a similar rocket.
    • Greg and Rodrick make a New Year's resolution to serve each other breakfast in bed, turning it into a contest to see who can do so for the most consecutive days, which Greg "wins".
    • A boy in Greg's year level gets beaten up for tap-dancing.
    • On St. Patrick's Day, Rodrick punches Greg, claiming he gets his "i"s and "u"s mixed up.
    • Greg follows a professional gamer, hoping to one day be on the video game circuit himself.
    • Greg's father tells him not to pick on Manny, which puts the idea to do so anyway into his head.
    • Piper Matthews (the equivalent of Holly Hills) was once embarrassed at wearing only underwear in front of her classmates.
    • Greg uses the confessional at his church.
    • Greg's father fills out a form offering to chaperone an end-of-year trip.
    • An entire plot line has yet to occur: Greg's father wants him to go to a specific high school, and his relatives give him clothes that are the same colour as the school's uniform. Mr. Heffley backs out of it, however, when Bill Walter says he went to that school.

The Books:

  • Accidentally-Correct Writing: In "The Meltdown", Rowley mentions being terrified of beavers due to seeing one attack a person in a cartoon, which Greg treats as a case of Rowley being a moron who Cannot Tell Fiction from Reality. Presumably neither Greg nor Jeff Kinney knew beavers actually have been known to attack and severely injure people with their powerful incisors, with at least one recorded case of a fatal beaver attack occurring in Belarus in 2013.
  • Approval of God: According to Jeff Kinney, the Goosebumps parody in Double Down had R. L. Stine's blessingnote .
  • Cowboy BeBop at His Computer: An official “lesson plan” set for the books claims to have the first page of the first book as a resource, but actually has the first page of the second book, Rodrick Rules. Considering that both pages are very similar, this mixup would’ve been easy to make.
  • Creator Backlash: Jeff Kinney disapproved of social media using Manny as a meme to promote the Black Lives Matter movement, feeling people were not taking the movement seriously.
  • Meme Acknowledgement: The 16th book in the series, titled Big Shot, has received attention from the Deltarune community thanks to the character Spamton being associated with the phrase. Jeff Kinney has acknowledged the meme, even jokingly stating that there aren't enough Deltarune-related tweets talking about the book.
  • Out of Holiday Episode:
    • The Third Wheel, which is all about the school's Valentine's Day dance, was released in November.
    • The Getaway, which is about the Heffley's Christmas vacation, was also released in November.
  • Refitted for Sequel: The Wimpy Kid Movie Diary: The Next Chapter revealed that one of the screenwriters' early ideas for the film adaptation of The Long Haul was for the Heffleys to be saved by a band called Metallichihuahua. This idea ended up not being used in the movie, but Metallichihuahua featured heavily in the seventeenth book, Diper Overlode.
  • Write What You Know:
    • Many incidents from the first book, such as Rowley breaking his arm and Rodrick telling Greg he slept through summer vacation, are based on personal experiences from Jeff Kinney's childhood.
    • Kinney tells a story in Poptropica about his experiences on the swim team. He describes that he'd hide in the bathroom and wrap himself in toilet paper for warmth, which Greg does in Rodrick Rules. He also talks about going off to a creek to catch tadpoles, only going back to the pool at the last moment. However, he once returned late, and his father caught him while he was still holding a bag of tadpoles. This incident was adapted into Old School.
  • Write Who You Know: Greg is based on all of Kinney's worst qualities, while Rodrick and Manny are based on his own brothers.

The Films:

  • Actor-Shared Background: Steve Zahn is just as enthusiastic about American Civil War history as his character, Frank Heffley, is.
  • Adored by the Network:
    • For a while, it seemed Cartoon Network couldn't go a month without showing one of the films at some point.
    • Even within the series, Rodrick Rules is played much more often than the other movies.
  • Blooper: In The Long Haul movie, Rodrick says that their mom doesn't know what it's like to be a kid in the 20th century, even though it obviously takes place in the 21st century. Of course, this is Rodrick we're talking about here.
  • Box Office Bomb: Diary of a Wimpy Kid: The Long Haul: Budget, $22 million. Box office, $20,541,739 (domestic), $33,561,079 (worldwide). The negative backlash over this adaptation replacing all of the cast from the previous three films (spawning the #NotMyRodrick meme), combined with the hiatus between the movies (as even creator Jeff Kinney stated there wouldn't be more films starring said cast due to the child actors growing older), critics panning it far more severely than the original trilogy and competition from Guardians of the Galaxy Vol. 2 dealt quite the damage to this film's overall performance.
  • California Doubling: Although the films are in set the fictional Everytown, America city of Plainview, the first three films were filmed in and around Vancouver, Canada. The fourth film has Atlanta, Georgia stand in for the Midwestern United States. Lampshaded in The Wimpy Kid Movie Diary:
    The producers searched for a place that looked like a typical American town. They considered Rhode Island, Michigan, and lots of other places in the United States. So it's weird that they ended up finding the perfect American town in Canada.
  • Creator Cameo:
    • Jeff Kinney plays Holly Hills' father in the second film and appears in The Long Haul as the guy at the Friendsville stand at the videogame convention.
    • David Bowers, who directed all the movies after the first one, appears in a newscast in the third.
  • Dawson Casting: Alf Humphreys was in his late 50's when playing Mr. Jefferson, who is almost certainly at least 10 years younger.
  • The Danza: In the first three movies, Rowley is played by Robert Capron. Rowley's name in the French adaptation is also Robert.
  • Fake American: Canadian Devon Bostick plays Rodrick.
  • Franchise Killer: The critical and financial failure of The Long Haul has all but killed off any hopes of future live action adaptations of the books. The next Diary of a Wimpy Kid film afterwards would be a Animated Adaptation of the first book.
  • Making Use of the Twin: In the first three film adaptations, Greg's toddler brother Manny was played by twins Connor and Owen Fielding. The companion book The Wimpy Kid Movie Diary notes how this was a helpful approach for dealing with young actors, since when one twin can't take direction, the other twin is available.
  • Non-Singing Voice: In the first film, when Greg is heard singing "Total Eclipse of the Heart", Greg's singing voice is performed by L.J. Benet.
  • The Other Darrin:
    • In the first film, Rowley's mom was played by Kaye Capron, Robert Capron's mother in real life. In the third film, however, she's played by actress Bronwen Smith instead.
    • The entire cast was replaced for the movie adaptation of The Long Haul.
  • Playing Against Type: Steve Zahn is known for playing lovable slackers, here he plays Greg's hard ass dad.
  • Separated-at-Birth Casting: The actors playing the Heffleys in the first three movies could easily pass for an actual family. In particular, the actors playing Greg and Rodrick (Zachary Gordon and Devon Bostick) could pass for brothers, and the twins playing Manny (Owen and Connor Fielding) look like miniature versions of the actor playing Frank (Steve Zahn).
  • Throw It In!: Rodrick crying during Patty's performance at the talent show in "Rodrick Rules" wasn't scripted. Devon Bostick was sad that they would be done filming soon and he'd have to say goodbye to his castmates, and the directors decided to leave it in the final cut.

The Animated Films:

  • Adored by the Network: Disney absolutely loves these films, as they had already green-lit the animated adaptation of Rodrick Rules a month before the release of the first film, and would announce an adaptation of The Last Straw a day before Rodrick Rules came out.
  • Channel Hop: As a result of Disney getting the film rights through their acquisition of 20th Century Studios, the animated film on Disney+ was branded as a Disney film.
  • Children Voicing Children: Ethan William Childress and Christian Convery were both around the same ages as Rowley and Fregley when they first voiced them.
  • Fake American: Canadians Erica Cerra and Chris Diamantopoulos voice Susan and Frank.
  • In Memoriam: The animated Rodrick Rules is dedicated to Ed Asner, the voice of Grandpa, who died a year before release.
  • Role Reprise: In the Italian dub, Giò Giò Rapattoni reprises her role as Susan from the first three live action movies.
  • Saved from Development Hell: An animated adaptation of the books had been in the works as far back as 2012, with Jeff Kinney announcing that a half hour television adaptation based on Cabin Fever (the sixth book) was in the works with a planned release for December 2013, which was then delayed to late 2014, before getting quietly shelved shortly after (likely due to the failure of the Dog Days film). It wouldn't be until 2021 that an animated adaptation would be made based on the books. It's not known, however, if the Cabin Fever adaptation morphed into the 2021 animated film or if the latter is an entirely separate project.
  • Self-Adaptation: The screenplay for the Disney+ animated film was written by Jeff Kinney himself.
  • The Other Darrin Cabin Fever recasts Greg and Rowley with Wesley Kimmel and Spencer Howell, respectively replacing Brady Noon and Ethan William Childress.
  • What Could Have Been:
    • As aforementioned, the first animated film originally started out as an adaptation of the sixth book — Cabin Fever — before it was shelved in favor of an animated adaptation of the first book. It would later be adapted as the third film.
    • Early footage of the film shows that the film was originally planned to be animated in a flat 2D-like perspective (similar to The Peanuts Movie) as opposed to the final film, which is animated in full 3D.
    • Disney announced an adaptation of The Last Straw a day before Rodrick Rules came out but the third film is based off of Cabin Fever.

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