Greg's dad used to say "If you get up again, you'll probably run into Shel Silverstein in the hallway." to scare him into staying in bed.
And he's still scared of that today!
The wasp incident in The Last Straw. All of it.
In case you didn't know, Leon Ricket who was both The Ditz and The Bully was put in detention for trying to hit a wasp that had landed on the window with a chair.
The scene in The Last Straw where Greg runs with his butt pointed towards the soccer coach when he yells "GET YOUR BUTTS OVER HERE!". Made funnier by the fact that he and his teammates had agreed to do it together — but the rest of the team just sat back and enjoyed the show.
Greg's short stint in watching soap operas in Dog Days.
When the character says "But Melissa, I love you", Greg says "Girlfriend, you can do SO much better than him!"
Also in Dog Days, Greg recalls a past incident in which he thought the the sign "Under 48''" Must Ride With Adult" at a water park meant people under the age of 48 must ride with an adult.
Greg's theory that Fregley is like a vampire and thus cannot come in uninvited leads to this daydream:
Nosferatu: Can I borrow some flour?
Greg: Sure, it's back in the kitch - hey, wait a second!
So Greg's mom signs up for a exercise program but she quits after the first class. But Greg's Dad takes a picture of her before her first class and receives duplicates from the photo place. Then, Greg's dad decides to write "Before" on one photo and "After" on the other. It's one of the funniest jokes he's ever made in the series. (Her cheerful thumbs up in the picture really sells it.)
The Ugly Truth has some delicious Cringe Comedy: when at a family gathering, one of Greg's relatives blurts out the REAL story of how his uncle proposed to his fourth wife: it turns out he was actually going to break up with her and go out with her sister, but was too chicken to actually say anything. Then when he planned to do it at a baseball game, a banner saying "Marry Me" with her name on it came by, and while he obviously didn't send it, everyone was looking at him so he proposed. The uncle tries to shrug it off but Greg tells us straight:
Greg: We're probably gonna be going to Uncle Gary's 5th wedding next year.
The various kids' comics in the Do-It-Yourself Book are all funny, but best of all is the blurb at the end of Greg's The Amazing Fart Police: "Next Week: The Fart Police Invade A Burrito Factory".
And the comic of that one where a duck actually crawled into the man's pants.
The lock-in in The Ugly Truth doesn't stop being funny, but the impromptu fake fart noises competition is a highlight.
One of 'em used a tuba!
When Greg says he can't open the microwave burrito packet, and Frank says that Greg would starve if he was stranded on a Deserted Island with just some water and a thousand microwave burritos, but Greg says that would likely never happen.
When Greg's mom tells him he'll be grounded if he lies again, and then tells him to lie on the phone that she's not there. So Greg, in a case of deconstructing one of the classic Parentisms of all times, makes his mom go outside and then says "mom is not in the house right now" on the phone so he wouldn't be lying.
When Greg and Rodrick fight and Mom holds a "Summit" for them, which consists of making someone draw a picture of the bad thing they did.
Greg's picture, captioned: I will not call Rodrick names.
(the picture has Greg saying "Bunny rabbit!" and baby Rodrick saying "Waaaah!")
Rodrick's picture, captioned: I will not push Gregory.
(the picture has Rodrick pushing Greg off a cliff into the mouth of a hungry shark, while Greg says, "Aieeee!")
Rodrick playing (read: getting out of) Magick and Monsters:
In the sixth book, Greg just found out that there was a blizzard. Rowley had called him to tell him there would be one the other day, however, Greg had dismissed that thought, because, according to him, Rowley calls every year around this time to say that a blizzard is coming. The reason why is because a couple of years ago, Rowley's parents had taped a Christmas special and the night they had taped it, a severe weather warning had been announced, so that was a permanent part of the recording, and Rowley takes it seriously. Greg used to fall for it, but he didn't after Rowley called him while watching the special on summer vacation to tell him a blizzard was coming.
The entire thing with Rowdy Riot energy drinks getting banned. In particular, the part where the kids who were forced to empty the cans sop up the puddles with their socks so they can still drink the stuff.
The picture of Grandpa Heffley standing on the toilet, smoking and the words "They don't need to convince ME it's not cool to smoke. My grandfather convinced me of that last Thanksgiving."
Of the many Chekhovs Gags in Book 9, the funniest turns out to be Rodrick's can of frozen cinnamon rolls. The family is driving through an area of woods where hunting is allowed, the cinnamon roll can explodes, thanks to one of the car's heater vents. It's night at the time, and when the back of Rodrick's head ends up covered in dough, he believes it to be his brains. And then he sees Manny licking dough off his fingers...
One from the very first book. Greg tells us about his school dividing the reading classes into "easy" or "advanced" lessons, and comments you can tell from which book they give you — "Einstein as a Child" or "Bink Says Boo". Greg, hoping to get out of any extra work, tried to throw the placement test so he'd be put in the easy group, but got placed in the advanced group anyway, suspecting that his mother stepped in to make sure he got put in the advanced group. But in the end...
You know, I'm kind of glad my plan to get into the easy group failed. I saw some of the "Bink Says Boo" kids holding their books upside down, and I don't think they were joking.
When playing dumb he reads "Fred picked up the buh-bah-bee..." and is told "The book?" and says "Phew, thanks".
From the tenth book: "In fact, the way we're headed, I'll bet a thousand years from now human beings won't even have SPINES." [picture of Greg slithering down a staircase]
The entire series of events starting with Greg, Frew, and Billy running away from the Girl Scouts in the tenth book.
Also in that book, is when Greg notices Frank has security cameras and Greg thinks there is one in Manny's stuffed duck, and says "I know you are watching me" to it.
And when Greg forgets to cap the toothpaste tube, so Frank tells him that if he was a kid growing up in frontier times and it was his job to tighten the bolts on the wagon wheels but he forgot to, then the wheels would fall off and the old-timey Heffleys would get eaten by Savage Wolves.
And later he drops the toothpaste cap down the drain and tries to get it out, causing a flood, which Grandpa fixes, but there is a water stain. He drives Greg into town to buy paint that would cover it up but has no license, so he goes the wrong way and causes the car to run out of gas. The community service gang show up, and one of them is Billy from before, so Greg hides while the teenagers eat lunch on the car,. When they get up, Greg's legs are asleep, so he grabs the console, which makes the car move into neutral and drives it into a ditch. He thinks if he could do it again, he would have left the toothpaste cap in the drain.
The argument about whether or not girls use deodorant.
When on a camp, the boys catch a fish and don't want to eat it, so Gareth puts it in the toilet.
When in the car, the pig sucks on a pacifier.
Not just the pig sucking on the pacifier. The whole scene qualifies as this. Frank drops his phone, the sunroof gets stuck, the car getting honked at, the pig trying to escape, Frank swearing, and the Spanish CD on full volume. It's chaotic, crazy, and absolutely hilarious.
And in the same book, Greg and the pig both have a Potty Emergency and it ends up with the pig using Manny's kiddie potty.
Greg says that it is awkward peeing with a "farm animal" next to him.
After the pig bites Greg, Susan can't find a doctor, so she takes him to the vet as an unaltered "pet human" where he gets weighed on the scale for dogs and Rodrick eats gerbil food.
Greg's essay on Chimps "This is a chimpanzee, or "chimp" for short. Chimps are supposed to be smart but I'm not sure that's true" and it has a chimp saying "Don't call me chimp" and someone else says "You are a chimp" and the chimp says "Oh yeah". Then on the other page it says "It looks like I'm out of paper so I guess this is THE END." At the real end, he says "I know it's really corny to finish with a Happy Ending, but it looks like I'm out of paper anyway, so I guess this is THE END."
Sweetie's dog bowl reads "SWEATY".
This line after Greg goes to the vet (long story) "Rodrick told me that when they take an ANIMAL'S temperature, they stick the thermometer somewhere ELSE, and that they probably use the same one for all their patients. I was worried that it was true, but then I realized that this was coming from a guy who was eating gerbil pellets.
In the movie, when Rowley grabs onto Rodrick's leg to let Greg escape. Rodrick's response?
Rodrick: "Let go, baby hippo!"
The scene from the movie where Greg pees on Rodrick.
A somewhat easier to miss one involving how Rodrick segues into the story; he states that the house was torn down because of it being haunted. Seconds later, in his tale, he states that it burned down. In-universe Canon Discontinuity much?
From the second movie, when Rodrick replaces the bathroom door with a spare door from the basement when graffiti is put on the former. Scared that his parents will find out, he tells Greg, "What about the D-O-R-E? The door!?"
"I'm a little birdie, I'm a little birdie - ow, my knee bone!"
In the climax of the third film, Rodrick decides to serenade Heather. Which song does he sing? "Baby". And it culminates in the two together... because her attempt at maiming Rodrick leads to them crashing to the floor together, covered in chocolate.
The scene in the third film where Rodrick tries to get the attention of Heather Hills by pretending he's drowning when she's doing lifeguard duty. She either doesn't notice him or simply doesn't care, and an older man who isn't in particularly good shape dives in to rescue him instead. Rodrick is understandably freaked out, but it doesn't stop there. He then proceeds to perform CPR on him. Poor Rodrick. It really is funnier than it sounds though.
Another one in the third movie, when the new family dog Sweetie chews up the meatloaf, Greg and his dad get Sweetie to let it go. Rather then make a new meatloaf, Greg and Frank put it back on it's plate, and the rest of the family doesn't notice.