Imagine Naruto joining the Akatsuki and immediately starting to redecorate their hideouts. He'd probably put up posters of his favorite things like Ichiraku Ramen and pictures of his friends. The Akatsuki members would be so confused, especially Itachi and Kisame, who are used to a more somber and serious environment. Naruto's presence would disrupt their usual routines and create all sorts of comical misunderstandings and situations as they try to adapt to his energetic and positive nature.
One possible hilarious adventure could be Naruto trying to convince the Akatsuki members to have a ramen - eating competition. He might use his charm and enthusiasm for ramen to get them all involved, and the sight of the usually serious Akatsuki members slurping down ramen would be quite comical.