These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Alternative Character Interpretation: Is the Boss a complete moron? A competent bureaucrat with a sociopathic streak? An initially decent guy made callous by a career dealing with idiot bosses and cynical employees?
Archive Panic - The whole archive is online - 21 years of daily strips - That's more than 7300 comic strips.
One series of strips involved Dilbert's co-worker growing a beard out of his forehead, which caused him to get promoted to manager. When Alice tried to kill him by pushing him down a flight of stairs, he died, but demons infested his corpse and he came back to life. Alice then tried to stab him to death with Dilbert's pen... at which point the whole arc just kind of ended. Even within the (already strange) confines of the strip, this arc is a whole new level of strange.
Alice killed the PHB in a different arc, but to fill the power vacuum she ripped another PHB out of a parallel reality to serve as their PHB. Also classifies as Status Quo Is God.
Asok once died, only to be reincarnated as a Snickers bar. Then used his psychic powers to change into a human.
Then the was the time Scott Adams got transported to the strip itself, which lead to a parody of The Wizard of Oz.
Dogbert:"A disturbing number of [the readers]'' have requested the return of Loud Howard. Loud Howard is neither funny nor insightful. He is simply loud. It's a wonder why anyone would want more of this guy.
Loud Howard:"THEY LOVE ME!"
It should be noted that after his first (and for the longest time, only) appearance in the strip Loud Howard was made a supporting character in the cartoon (shouting the obvious works a lot better as a gag in animation) in order to expand the cast. Had Adams not done this it is doubtful the masses would've demanded his return to the strip.
Catbert, notable for being the only character the fans named (see Sure, Why Not? below).
Genius Bonus: The fable that the Pointy-Haired Boss relates in this strip is traditionally used to explain the Scrum software development methodology. If you're not familiar with Scrum, the strip is still very funny, but if you are, it's clear that the PHB thinks himself clever for using an analogy that he read somewhere else and probably doesn't understand.
Memetic Mutation: According to Adams, the term "Bungee Boss" has entered the business lexicon for the situation WhenTheNewBossWantsToChangeEverythingButOopsTooLateHe'sReassignedGoodbye.
Happens rather often. Just read any list of New Century Business Jargon; a lot of it will have come out of Dilbert.
The term "Pointy-Haired Boss," aside from being a Trope Namer, is almost ubiquitous (as is the derivative "pointy-haired" as a synonym for "stupid").
One-Scene Wonder: Loud Howard has been in exactly three strips to date, one of which was Adams Breaking the Fourth Wall to complain that he didn't understand why people were so interested in a one-joke character. He was popular enough with readers that the Animated Adaptation made him a recurring character. Loud Howard also had a whole bunch more jokes in the animated series, most of which wouldn't work in the strip format.
One Sunday strip featured a security guard who secretly raided the employees' hidden snack stashes during the night. Whoever did the colors made him black, which lead to people accusing Adams of this (in the anniversary book, he explains the whole thing while wryly observing that they chose a poor time to diversify the cast).
Write What You Know: Dilbert started running while Adams was still working at Pacific Bell, with Wally being mostly a non-speaking background character. Then the company began offering buyout packages to the employees, with the caveat that they were only available to the lowest 10 percent of the workforce(as a way to get rid of deadweight). One of Adams' coworkers(who Adams describes as "one of the more brilliant people I've ever known") decided that was a fine idea and began to "work as hard as he could to become the worst possible employee in order to get money for leaving", which included openly running a side business from his cubicle. Adams loved the concept of a cynical employee with no loyalty to his employer, and Wally was born.
The TV series:
Critical Research Failure: In "Y2K", Dilbert's "perpetual calendar program" predicts that June 30, 2014 will be a Thursday. It's actually a Monday.
Crosses the Line Twice: Alice marries a death-row inmate and immediately stuffs the gag into his mouth herself before he's executed. It's much more horrifying than it sounds.
Harsher in Hindsight: These days someone walking into a government building strapped with dynamite (which they then prepare to light) isn't so funny anymore.
The scenario of a crochety old lady who only owns one share of a failing company rambling about irrelevant things at a stockholders' meeting may sound familiar to fans of a certain other show that came much later. The fact that said old lady is voiced by thesame person certainly doesn't help.
Ho Yay: The scene from the merger episode where the process of finding a merging partner is played out like someone looking for a sex partner. Including the part where an executive tells the Pointy-Haired Boss that he wants to merge with him right there in the bar.
The PHB accuses Dilbert of this after the latter saves his life via CPR. In addition to assuming Dilbert tried to Date Rape him.
Magnificent Bastard: Dogbert, whose "religious belief" is "that everyone exists for the sole purpose of entertaining me." On one episode, he sets up a carnival booth where you "knock a street urchin off a beam with a baseball and win a toy." In another, he convinces Congress to abandon all holidays in favor of National Dogbert Day (The traditional Dogbert Day feast: the bald eagle. He wanted something special) for the sole purpose of being annoying. (The same reason he invented Secretary's Day.)
The aptly named Bob Bastard, the caped and hooded company tester on a quest to crush the hopes and dreams of engineers.
Dilbert: I'm sorry Alice, but he's the embodiment of all that's horrid and loathsome in this world. Alice: Just because it's written on a bathroom wall doesn't mean it's true. Dilbert:He wrote it!
Nightmare Fuel: When Loud Howard sneezes, hit the floor. Lest ye have your flesh torn and your body stripped right down to the skeleton.
Lena and her nasty collection of still-living heads from the men she's decapitated in order to steal their ideas.
The alien merger shown draining human heads
Ugly Cute: The Dupeys, even after they've grown up past their cute point
The Woobie: Dilbert in many cases given how he's often trying to remain somewhat optimistic despite the world he lives in. Not to mention the crap he takes from virtually everyone, including his own mother.