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• Almost any scene with Halt on a ship. period.
• Horace mentioning Will's drawing skills (or complete lack thereof). Even Malcolm gets in on it. Will isn't laughing.
• In the eleventh book, The Lost Stories, more than half of the short story "Purple Prose" might make you laugh at loud.
• The Entire scene from the beggining of Sorcerer in the North, where Will defuses a standoff between desperate Skandian raiders and his fief by Inviting the Skandians to a feast at the castle. Hilarity Ensues
• Despite above mentions of his artistic skill, Will is pretty good on the Lute. Actually, it's a mandola. He's also made a song about his mentor, Halt.
• When Will is awarded the Silver Oakleaf in Erak's Ransom, Alyss and Evanlyn are the ones to place it around his neck. Upon doing so, both of them impulsively kiss Will's cheeks and then glare daggers at each other.
• Halt's obsession with coffee is often brought up, and just as often hilarious.
  • Not to mention his preference for honey in his coffee, which is treated by the other Rangers (including Crowley and Gilan as a Bizarre Taste In Food).