Mr. Boss (or just The Boss) is the head of Smiling Friends Inc. Within the show, he is a minor character who usually briefs his employees on their work and clients. He is voiced by Marc M.
Appearance
Body
Mr. Boss looks like an elderly man with a big head and a thin body. He has thinning hair with dark gray hair on the top of his head and white hair on the sides. In some of the close-up shots, he has a faded bruise on his forehead. In “Desmond’s Big Day Out”, he is shown pulling out a breast from under his shirt, which he uses to feed his son; however, in “Frowning Friends” and “Charlie Dies and Won’t Come Back”, he is seen shirtless without any visible breasts. Despite this, his son can still be seen, which casts doubt on whether he actually has breasts or not. It’s possible that he only has them sometimes, or he may have lost them since they were last seen.
Clothes
He wears a dark blue suit with a white shirt and a yellow bow tie. He puts on a black and green headset while playing.
Personality
Mr. Boss is a highly eccentric but very friendly individual. He treats his employees politely and casually and seems to genuinely trust them and consider them his friends. He is also very passionate and enthusiastic about running his business as he is always quick to respond to clients regardless of the occasion (although he sometimes plays video games in his office). Like Charlie and Pim, he also has a knack for making people laugh and seems to be even more adept at it than his own employees when the situation calls for it.
Contrary to his genuinely friendly and kind nature, Mr. Boss is prone to very odd behavior and mannerisms, and it is strongly implied that he has some sort of mental illness. He has a habit of switching out of nowhere into a deadpan but menacing Southern accent when speaking, seemingly to make his co-workers slightly uncomfortable. In “Mr. Frog”, he is seen walking the halls while haphazardly eating a plate of spaghetti[1], and in “Shrimp Odyssey” he casually mentions eating some of Alan’s worms. In “Stupid Halloween Special”, he is shown among the many partygoers who attacked the forest demon for “wearing a black face”, feasting on one of his severed arms before throwing it into an internal fire made from his brutal remains. While facing competition from Cloudy Friends, he was driven to “jealousy” and consulted fictional versions of Warren Buffett, Mr. Peanut and Ronald Reagan for business advice. When that failed, he was reluctantly convinced to kill his competitors with an evil split personality. Along with them, he has some sort of mental breakdown at the end of Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director’s Cut). Despite his apparent insanity, he is also shown to have a strong enough moral center to overcome his urges and quickly snap out of his murderous rage when Grim begins to plead for mercy.
Background
Nothing is known about Mr. Boss’s story yet.
Relation ships
Kaia
Mr. Boss is Charlie’s employer. They seem to be on pretty good terms with each other and are never shown to be arguing. He even said a few words about him during Charlie’s funeral in Charlie Dies and Won’t Come Back.
Pim
Mr. Boss is Pim’s employer. Mr. Boss is shown to have a special trust in Pim, given that he recruited him to collect wood for the Halloween bonfire.
Alan
Mr. Boss is Alan’s employer. They seem to be on pretty good terms with each other, considering they’ve never been shown to bicker. Alan voluntarily checks on Mr. Boss during his mental break in “Frowning Friends”, indicating that he cares at least a little.
Goof off
Mr. Boss is Glep’s employer. They seem to be on good terms, but it’s hard to tell, due to the fact that Glep speaks his own language, until the end of “Charlie Dies and Won’t Come Back” he’s never shown to actually speak English.
Boss Baby
She has a decent father-son relationship with her young son and openly breastfeeds him in front of her staff.