This discussion may contain spoilers!
Yeah, I know, sooner or later, the unoffical "Did You Try?" list will be revealed, and then later, the offical "Did You Try?" list. Still, I like to reveal it...if only because, well, it's fun.
EDITED IN: Inn
Try to open the door before and after you recruited the Innskeeper in your party.
Ask the Innskeeper about Ye Flask.
Try to get Ye Flask 4 times.
Talking to Strong Sad
Talk to Strong Sad using the angel option twice.
Talk to Strong Sad using the devil option three times.
Complete the "Strong Sad fetch quest" over and over until he asks you to get the "Thing of Thingy".
Trodgor's Lair, FPS
Use all your Party Members to defeat each of the enemies to quickly bypass the level...
Or don't use the Party Members at all and use the 'long path', and meet up with Trogdor early!
Get your health low enough to get the Health Pack to spawn. Grab it.
Get your Light Gun ammo low enough for the Light Gun ammo pack to spawn. Grab it.
Try to get killed by Trogdor or the KOT during the FPS segment.
Disarm the KOT and let him say his last words.
Use all your items OTHER than the Trog-Sword. Marshie and the Light Gun for instance.
During the entire battle, set your Hints up to high to listen to Homestar Runner's 'advice' during during the battle.
Talk to Homestar Runner twice before using Marshie.
Talk to Homestar Runner twice after using Marshie.
Talk to Homestar Runner after killing Ultimate Trodgor.
EDITED: Added stuff that you could do at the Inn.