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"That's the Circus Leader's Mask, isn't it? That is a fine mask. It is filled with the feelings of tenderness left behind in the back of one's heart." -Happy Mask Salesman
This Mask is obtain from Gorman to show his gratitude. When worn the mask constantly "cry" and get reactions from people who are related to Gorman, such as the Gorman's brothers, they will restrain from saying any rude comments to Link while he is wearing that mask.
How To Obtain
To obtain the Circus's Leader's Mask, Link must first gain acsess to the Milk Bar. To gain acsessm, Link must first obtain the Romani's Mask, obtained by helping Cremia. Link must have also obtained the Zora's Mask. Once inside the Milk Bar Link must help Gorman play the Ballad of the Wind Fish. Link must play a segment of the piece as each of his forms. Gorman will be so moved by the piece so much he gives Link the Circus Leader's Mask.
When helping Cremia defend her cargo as she rides in to town from the Gorman's Brother disguise in Garo's masks, if Link wear the Circus's Leader Mask they will cease their attack until Link removes the mask. This does not help seeing as Link must do the quest to obtain the Circus's Leader Mask.