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]]. 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!!]]''
** Tasering Strong Bad during Baddest of the Bands. [[CrossesTheLineTwice Repeatedly.]]
* ''Strong Bad's Cool Game for Attractive People'' features [[spoiler:Strong Bad learning Homsar's language]] in ''Strong Badia the Free''.
* 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 two, both by getting the better of Strong Bad. The first one is 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!" The second one is pretty much the entire plot of ''Strong Badia The Free''. For those who don't want to play it, here's the basic story, summed up in all its spoileriffic glory.
** [[spoiler:The episode opens with Strong Bad receiving an email from someone named Roy T, asking Strong Bad if he thinks he would be a better ruler than the King Of Town. As Strong Bad replies, the KOT himself suddenly bursts into the room, along with the Poopsmith, dressed in riot gear. He explains about his new email tax - one Creamy Ding Snack Cake for every email sent or received - and that Strong Bad is in violation of it. When Strong Bad refuses to obey the new law, KOT has him put under house arrest, in a way that makes him seem less like a bumbling, ineffectual ruler and more like a ruthless dictator. Strong Bad eventually escapes and decides to make Strong Badia its own independent nation, aiming to overthrow the King Of Town. After conquering most of the other characters' nations, Strong Bad and Homestar lead the Homestarmy on a full-scale assault on the KOT's castle. After hours of ferocious fighting... well, actually, the KOT gives up after about five minutes, and Strong Bad takes over the castle. Discovering that the King has a computer, he checks the King's inbox, only to find an email in the "Sent Items" folder... signed "Roy T." The EXACT SAME EMAIL Strong Bad received in the beginning of the episode. The King Of Town sent Strong Bad that email to TRICK STRONG BAD INTO OVERTHROWING HIM. Because he was tired of being the King. Now Strong Bad has all the responsibilities, while the KOT (now known as the Of Town) gets to kick back and relax in Strong Bad's house. It doesn't last, of course, but the KOT pulling something like this is seriously awesome in my eyes.]]
* KOT got another one in Baddest Of The Bands, where he actually (without even trying, and with Strong Bad's "help", no less) UPSTAGED Strong Bad during their performance. The KOT getting the better of Strong Bad seems to be a recurring theme.
* From ''Strong Badia The Free'', Homsar's lines to Strong Sad if the two meet during the Maps And Minions game. For what Homsar usually is, those lines make him sound almost Badass, especially "I'm the long way back from naptime!"
* Homestar's singing voice in Baddest Of The Bands.
* Strong Bad defeating TROGDOR in 8-Bit Is Enough. Trogdor, who's supposed to be IMMORTAL. TWICE. Though it's implied that was AllJustADream.
** Also from 8-Bit Is Enough, Trogdor's introduction is deliberately made awesome.
-->'''Strong Sad:''' It sounds like the fan's broken! You'll have to get it serviced!\\
'''Strong Bad:''' Serviced? Where am I supposed to get FAN SERVICE around here?\\
''(The 8-Bit version of Trogdor's theme blares as the Trogdor machine grows wings, legs and a beefy arm and proceeds to chase everyone except Strong Bad out of the room)''\\
'''Strong Bad:''' That... may be... the coolest thing... that has ever happened.
* Marzipan, despite being TheScrappy due to her preachy ways, gets a few in Baddest of the bands in the two easter eggs where she pummels Strong Bad.
** She and Cool Tapes was Limozeen's favorite band. And some SugarWiki/AwesomeMusic to boot.
** Marzipan beating up Strong Bad was a bit of a small running joke. In Episode 4, Dangeresque 3, Strong Bad has to distract Marzipan to get some of her hair. When he does succeed in doing that, it cuts to Strong Bad pulling a pencil out of his head (mask?), implying Marzipan practically harshly injured Strong Bad.
* 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 ''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.]]