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Bob Ross is a painter on Counterfeit Island. He can be seen selling his paintings on Main Street (Counterfeit Island) in front of the Moldy Baguette Inn.
Bob Ross is a painter most likely based off of the real painter of the same name. He has a grey hair Afro and circle beard. He wears a blue v-neck sweater over a white dress shirt and brown pants. Not much is known about his personality, but he is certainly astute enough to notice suspicious things, such as why the Investigator would buy a frame-less painting.
Most of the time, Bob is standing outside the Moldy Baguette Inn selling his paintings. Partway through the island however, after talking with the Curator, Bob tells you about how he recently sold a frame-less painting to the Investigator, which he found suspicious. It is later revealed that the painting was used to cover up "The Scream" painting which had been stolen by Black Widow, disguised as the Investigator.