From Homestar Runner Wiki
I'm Tim, a long-time Homestar Runner fan (little questions was new when I first visited the site) and fairly long-time Wiki lurker. I haven't made any big contributions besides creating the Flipped Images page and transcribing some commentaries found on the Greatest Hits DVD. My commentary transcriptions so far: 50 emails, pizza joint, slumber party, your funeral, kind of cool
My favorite toons are those that feature some good Homestar interaction. The email stupid stuff, besides offering some great lines about Grumble/Cheatcakes from Strong Bad, has some great Homestar moments like the "standing on one foot" gag and his attempts to look a smart by speaking "Science!" into a test tube. Homestar crashing Strong Bad's party in do over ("I need The Cheat!" "Oh, okay. Meh."), car ("Did you just say doyng?"), the facts, and long pants are a treat, although those don't seem to be many people's favorites.
Homestar also has some great Answering Machine moments, especially his message as a telemarketer in #4: "I can give you rates as low as anybody. Seriously. I don't know what they are... but I probably could give them to you." Or his sad imitations on #9, especially his self-imitation: "Let's have a marriage. Let's have a marriage license."
In my opinion, Homestar Runner is past its prime, but still has some quality stuff for a fan. While the occasional callback is nice, it seems like some toons' humor is overreliant on inside jokes and references. The callback to guitar in dragon was cool, and made sense; it was even relevant to someone who would only watch dragon. The Animated Adventures of Puppet Homestar and email thunder have almost zero value outside of callbacks, and they're not particularly funny ones, just sort of acknowledgements. That being said, this wiki claims there to be way too many gags/jokes. Blood, pudding, non-trophied pizza, french fries, and cross-dressing are not running gags.
A lot of the old Tandy-era emails weren't really that funny, but they did have some cool Strong Bad characterization that later went away. For instance, in band names, Strong Bad cleverly referenced a number of 80s metal bands. Nowadays, we'd just get vague parodies in the guise of Limozeen, which is okay and all, but overdone. He went from a slightly self-absorbed bully who was cool ten years in the past to a Brothers Chaps mouthpiece for making parodies of old cartoons, pet shows, magicians, indie films, workplaces, hair & death metal, garage sales, breakfast cereal... whatever he gets emailed about, he'll just make some direct parody/mockery of now. I suppose he made fun of anime and drawing tutorials in the site's height of popularity, but I'd still prefer more characterization and less callbacks and parodies. Especially lady...ing-style self-parodies, mixing the worst of both worlds.
One thing I love about the site, and has remained a feature still, is its interesting use of the English language. From little things like be's/besing or "three o' dems" or "I'm've was to make football often times" to the incoherent ramblings of Homsar, Senor Cardgage, or Shark-Tooth Bubs, there's stuff to be enjoyed. You can throw in an occasional "juys," "combolations," or "What it is, my doge?" in conversation without requiring the listener to be a Homestar fan. Of course, it's enhanced if the other person IS a fan, and that's what I appreciate most. Humor that is enhanced by knowledge of the site, but not requiring it.