With a cartoon running on the RuleOfCool and RuleOfFunny, it is no surprise that WebAnimation/HomestarRunner has several several awesome moments.

* Coach Z, of all characters, gets one in Loading Screens, doubling as SugarWiki/AwesomeMusic. He sucessfully freestyles. About [[MundaneMadeAwesome loading screens]], but still. This earned him more fandom than any other cartoon before.
** He was no slouch in [[http://www.homestarrunner.com/rapsong.html Rap Song]] either. Coach Z definitely has the rhythm in him, even if his lyrics are gross.
** Coach Z has definitely been getting better at rapping over the years. This example from Fish Eye Lens is definitely impressive:
--->Now let's pretends I got ten girlfriends\\
I make amends in my Benz with the fish eye lens
* Strong Sad surprisingly gets a lot, mostly due to his DeadpanSnarker attitude.
-->Did your terrible computer explode?
-->Did you get '''400,000''' viruses?
-->Um, ''excardon'' me, but none of that stuff is cool, Strong Bad.
-->There needs to be a better word for weird.
** And beating Coach Z up in a mad frenzy, whilst spouting defining CrazyAwesome the whole time.
** In the "rough copy" email, the snowball sequence. Someone pelts you with balloons? Throw permafrost at them! Strong Sad has kept some ''[[{{Hammerspace}} in his notebook!]]''
--->''[[CrazyPrepared I've been saving these [snowballs] in the freezer since I was eight!!]]''
** In "your edge", Strong Sad tricks Strong Bad into staying in the basement for several days by claiming websites said it was edgy to do so... and then walks away without looking back.
* Homsar scored one in the 2007 Halloween toon, by basically absorbing the Jibblies and sending it back at the painting, giving IT the Jibblies.
* Strong Sad of all people gets one when he successfully uses illusionary magic to scare Strong Bad in Email 196.
* The King Of Town got a minor, but still pretty cool, line in one of the Halloween cartoons, after Strong Bad makes fun of the Poopsmith dressing up as Lazer Tag. "Ease off, Strong Bad! He's not the one who dressed up as a GIRL two years in a row!"
* Pom Pom writing, producing, directing and distributing a feature film in the course of a few seconds, using his cell-phone. He then gets invited to the Sundance Film Festival.
* In [[http://www.homestarrunner.com/sbemail58.html dragon]]:
-->'''Strong Sad''': ''(holding an advanced drawing of a dragon)'' I think I've improved on your methods a bit, too. I employed some chiaroscuro shading, and-\\
'''Strong Bad''': I'll improve on your methods!! ''(sets Strong Sad's drawing on fire)''\\
'''Strong Sad''': What? That's not an improvement.\\
'''Strong Bad''': BWAHAHAHA! Trogdor strikes again!
* In [[http://www.homestarrunner.com/sbemail101.html this email]], Strong Bad writes the word 'Deleted' backwards in fancy English font and proceeds to punch Homestar, leaving the words on his face.
* A fan got one in [[http://www.homestarrunner.com/costumes2009.html the 2009 Halloween Costume Commentary]].
-->''(a picture of a man dressed in a costume incorporating sunglasses and a fedora appears)''\\
'''Strong Bad:''' I give up. You win. I have ''no'' idea what you're supposed to be.\\
'''Strong Sad:''' Well, allow me to explain.\\
'''Strong Bad:''' OH, GREAT!\\
'''Strong Sad:''' He's not simply ''(a picture of a Pom Pom costume appears)'' dressed up as a character, or ''(a picture of a costume of Professor Experimento, played by Pom-Pom)'' a character dressed up as someone else, or ''(a costume of Homestar and Strong Bad as MobileShrubbery appears w/ screenshot)'' a character dressed up as some''thing'' else, or ''(a costume of the detective from ''Where's An Egg?'' w/ character sprite)'' a character from a video game, or ''(costume of Strong Sad as Garden Boy w/ screenshot)'' [[ButHeSoundsHandsome a really cool character dressed up as a super cool guy all the time character]], or ''(costume of "Stave It Off" guy)'' that "Stave it Off" guy-\\
'''Strong Bad:''' I call him Stave!\\
''(costume of "the svelte, young Prince of Town" w/ screenshot)''\\
'''Strong Sad:''' Or an ''alternate version'' of a character. No, no hohoho! ''(sunglasses and fedora costume reappears)'' He's dressed up as an alternate drawing ''(screenshot of The Cheat)'' of an alternate version of a character ''(screenshot of Gunhaver)'' from the Sketchbook! ''(screenshot of [[{{Omake}} a sketch depicting Gunhaver as a human]])''\\
'''Strong Bad:''' All right, that is (a) amazing, (b) depressing, and (c) amazingly depressing.
* In "stupid stuff", Strong Bad makes a bet with Kevin Grumbles that if Strong Bad can make Homestar say something smart, he gets some Grumblecakes. While he is trying to achieve this task, this exchange occurs:
-->'''Strong Bad''': ''(to self)'' Maybe if I employ a little reverse psychologies... If I ask a stupid enough question, I'll get an intelligent answer! ''(to Homestar)'' I say there, Homestar, butt's twelve by pies?\\
'''Homestar Runner''': Ooh, yes! [[BatmanGambit I got Strong Bad to say something stupid!]] The Grumblecakes will be mine! ''(walks off)''\\
'''Strong Bad''': What?! What the crap just happened?! Is it possible that I was just... ''outsmarted'' by ''Homestar Runner''?! [[SoreLoser I'LL GET YOU, KEVIN]] ''(grumbles)''!!!
* Strong Sad catching Strong Bad off of his game (even if only for a moment) by changing Marzipan's answering machine message. Strong Bad calls to leave one of his trademark prank calls, but is shocked to hear Strong Sad!
-->'''Strong Bad:''' Wait, what?! Hold on; I wasn't prepared for this. Just gimme a sec. ''[Hurriedly writes something down]'' Okay, I'm ready. ''[Reads in a struggling tone]'' "Yes, this is...Strong...Bad...calling for...Strong...Sad...uh, I'm gonna...knee you in the face...for...breakfast?!" Hold on! Let me reconfigure and call back.
* As the Cheat's "career" in animation goes on, he's done music videos for not just Strong Bad, but big-name musicians like Taranchula, Limozeen, Peacey P, and even ''Music/TheyMightBeGiants''. Not only that, but his animation has definitely gotten more impressive as time has gone on ([[http://www.homestarrunner.com/rapsong.html "Rap Song"]] in particular has rotoscoping and other effects in it.)
* Out of universe, the fact that the website was able to release almost all of its content on DVD, have a music CD, and have an episodic game made by a development team the creators admired greatly when growing up.
* 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. True to his word, "[[http://www.homestarrunner.com/fisheyelens.html Fish Eye Lens]]" became the first official release to the site on October 3.
* April Fools 2016 brought us a 30 minute long Marzipan's Answering Machine, in which [[spoiler: the Poopsmith breaks his vow of silence once again.]]
* Speaking of Marzipan's Answering Machine, "personal favorites" shows some of Strong Bad's personal favorite e-mails, the first two of which definitely happened, the rest of which seem to have been made up, and yet one of which, in particular, does seem to account for exactly what happened to Marzipan's original answering machine... by virtue of having left such a good crank call on it that it exploded.
-->'''Marzipan:''' (on answering machine) Hi, this is Marzipan.\\
'''Strong Bad:''' CRANK CALL!!\\
[The answering machine explodes.]
** ...which turns the above into a CallBack [[spoiler:when the ''new'' one explodes as part of a years-in-the-making April Fools that leaves Strong Bad baffled on the floor. "April Fools', Strong Bad!"]]
* In the email "pom pom", Strong Bad attempts to poke Pom Pom with a pin while setting him on fire. The first time he misses due to being blindfolded. The second time his aim is accurate... and Pom Pom dodges the attack, ends up behind him, and gets ''seven'' consecutive hits on Strong Bad, which sends him flying all the way back home from Bubs' Concession Stand before he could touch Pom Pom.