Go to the photo booth and aim your Wii remote towards the top of the light closest to The Cheat. Move the cursor around until you notice it change and press A. Hold the A button down and drag the shirt to Strong Bad for him to wear.
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Strong Bad's Cool Game for Attractive People: Homestar Ruiner - WiiWare Hints
To get the hedge Trophy, cut all of the cut-able hedges in front of the King Of Town's Castle, on the side of Marzipan's House, at the Track, and to the right of the Stick or the Photobooth (I can't remember, sorry =/).
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