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.
Big Name Fan: Due to the site's popularity, there are several. In fact, there are so many that the fan wiki has to use multiple pages to list all the references to the site in pop culture.
Creator's Pet: Strong Bad. Starting off has an Ensemble Darkhorse, it seems his popularity has gone too far. What with him being the star of the official game based on the website as opposed to Homestar, and receiving more exposure than all other characters (again, including Homestar), even going as far as to exert his popularity over Homestar in cannon, has certainly gained him more than a few haters.
Crosses the Line Twice: A lot of Strong Bad's abusive behavior would be horrifying in just about any other context, but it often ends up being so ridiculously over-the-top or childish/ineffective that it becomes hilarious rather than disturbing. However it can occasionally go a bit too far in this direction; see the entry for Dude, Not Funny! below.
Dude, Not Funny!: Really, a lot of Strong Bad's abuse of Strong Sad isn't funny. How he annually boards up Strong Sad in a bathtub around Decemberween comes to mind.
There's also the toon where Homsar is starving to death in the snow with his body caved in. As if that wasn't bad enough, the series went on hiatus with the last toon having no appearance or mentioning of Homsar.
Ear Worm: Quite a few, including "The System is Down!", "An Important Rap Song", and "One, Two, One, Two..."
Near the end of "Fall Float Parade," a giant Marshie Balloon feebly controlled by The Cheat rams into the platform where Marzipan and Coach Z are reporting. This became less funny when three days after the cartoon was posted, a Macy's Thanksgiving Day Parade balloon accidentally slammed into a streetlight, injuring two people.
"Best Caper Ever", which is about Homestar floating on an ice floe through the Arctic as Strong Bad and The Cheat try to remember what happened, came out February 9, 2009, one day after 134 people were rescued from a freeflowing sheet of ice that broke off into Lake Erie. Because of this, the page title of the cartoon was "Total Coincidence! Not Intentional!".
Harsher in Hindsight: In "Sbemailiarized Entertainment," Mike Chapman says he "can't wait to stop working– start working. On them." Not long after, the franchise would enter a lengthy hiatus.
In the commentary (published early 2001) for The King of Town, Strong Bad complains about not having his own cartoon. The following August, the first Strong Bad Email was put on the site, and Internet history was made.
"Attention Holiday Shoppers! Bubs Friday starts Thursday!" The last item in a "not Football TV" montage back on Thanksgiving 2007. Four yearslater...
In the 2008 Halloween cartoon "Most In The Graveyard", Coach Z dresses up as DJ Lance Rock from Yo Gabba Gabba. Matt Chapman has since become a writer for said show.
"A Jorb Well Done" became this after South Park's "Goobacks" had its own mispronunciations of "job".
Homestar: Strong Bad, your costume is making me feel (suggestively) loosey-goosey!
Strong Bad: Shut your face pile right now, or I'm gonna start feeling a little punchy-wunchy.
In this cartoon where Strong Bad is making fun of Halloween costumes, there is one of a girl dressed up as Homestar Runner, which leads to conflicting feelings on the subject. Then Homestar Runner pops up and starts calling him 'sweetie.'
Rescued from the Scrappy Heap: The King of Town was formerly regarded as a dull, one-trick pony and as such, was far and away the least popular character on the site. A combination of Flanderization and his own amusingly pitiful attempts to boost his status gradually endeared him to fans.
Shallow Parody: The 20X6 series. The Brothers Chaps aren't really all that up on anime, and it shows.
Stylistic Suck: Some (not all) of the Shallow Parody factor can be blamed on Strong Bad in-universe, who wrote the premise of Stinkoman based on one episode of one anime that he watched several months prior.
Tear Jerker: "Sick Day." You can't help but feel sorry for everyone in this one. Strong Bad is so ill that he's taken refuge under his desk and is rendered incapable of answering the latest email, The Cheat is sobbing in a bucket of puke, and Strong Mad is crying for help in his quarantined room. Homestar's ill to a delirious extent as well, though it's hard to tell if that's just his normal countenance or if it's compounded by his sickness.
An in-universe example in "Homestarloween Party"; everyone takes turns in adding to a supposedly scary story, and when it's finally Strong Sad's turn there's a robot and the Goblin. Strong Sad's addition to the story results in the formerly-human robot remembering its humanity, crying, shorting itself out, and crushing its two human grandchildren and the Goblin. "And no one lived." Everyone else is reduced to tears, and Marzipan tells Strong Sad that he's banned from next year's party.
The April Fools' 2014 toon, which was the first toon in nearly four years, can easily strike a chord. It starts out with the once-happy page welcome screen having fallen apart, then goes through a number of features from the site's older days that the same people who would rejoice at an update in the first place are bound to remember fondly. At the end, there's a reprise of the already-heartbreaking Homestar Windows 98 Shutdown Song, and Homestar and Strong Bad just chipperly discuss the possibility of another update in three, five, maybe fifteen years. It gets worse in an Easter Egg, where they reveal that they've done absolutely nothing with their lives in all this time, Homestar himself even living in a moldy duffel bag.
As of July 2014, Matt Chapman confirmed on the Jeff Rubin Show that he is back in Georgia and seriously wanting to bring back the series. Elaborating that they never wanted to stop the show for so long, but after Matt's second child, it gave them the opportunity to answer the animation studio people they've been contacted by over the years, resulting in 4-5 years of professional animation work. With Matt back at home living close to Mike, they plan to rev it back up sometime in Summer-Fall 2014.
Unpopular Popular Character: Coach Z. While most of the main characters besides Bubs and Homestar have difficulty putting up with his awkwardness, some fans find the same hilarious awkwardness endearing.
Also the King of Town.
The Woobie: Coach Z spends Decemberween trapping himself in his locker and drinking Listerine.