This is Pineapple, the 11th Place finisher of Season 1.
Because he's the oldest of the masks, Pineapple has seen and been through more than the other masks, so he usually takes things as they come and never wipes the smile off his face. But this doesn't mean that he never worries at all, for the record. Sometimes he really is worried and just smiles to hide it (although his true emotions always manage to come out anyway).
Besides being laid back, Pineapple can also be a very fun guy to be around. In my AU, he has a pet scarlet macaw named Cheech. He and Cheech the parrot are the masks' equivalent of Tommy Chong and Cheech Marin.
PERFORMER: Tommy Chong
STRENGTH: Goes well with ham
WEAKNESS: Ripens quickly
LIKES: Surfing, ham (don't tell Piglet), the tropical aesthetic, being happy, telling jokes
DISLIKES: Cold weather, Cheech talking back at him
YOU ARE READING
The Masked Singer Headcanons
FanfictionThe book is about my AU building, and character headcanons. I recommend you read this book before reading my other Masked Singer books.