The trick H*R Wiki used is far more simple than the regular, traditional way of jumping through space and wandering blindly.
Here's how they did it:
"Enter the photo booth, interact with the top of the light closest to "The Cheat". After the pointer changes shape, keep holding down the interaction button and drag the shirt onto Strong Bad to wear it."
While the actual shirt bears little resemanblnce to Sam and Max, the icon that you drag down onto Strong Bad looks very similar to the Sam Crossbones.