The Boss

"Now get out there and make someone smile." The Boss is the head of Smiling Friends Inc. Within the show, he is a supporting character who typically informs his employees about their jobs and clients. He is voiced by Marc M.

Body
The Boss appears as an elderly human man with a large head and thin body. He has thinning hair with a patch of dark grey hair on top of his head and white hair on the sides. In some up close shots he has a faded bruise on his forehead.

Clothing
He wears a navy blue suit with a white shirt and yellow bow tie.

Personality
The Boss is a highly eccentric yet very friendly individual. He is polite and casual around his employees, and he seems to genuinely trust and regard them as 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 (though he sometimes plays video games in his office). Much like Charlie and Pim, he also has a knack for making people smile, and seems be even more skilled at it than his own employees when the situation demands it.

In contrast to his genuinely friendly and kind disposition, the Boss tends to engage in very odd behavior and mannerisms, and is strongly implied to have some sort of mental illness. When speaking, he has a habit of switching to a deadpan yet menacing southern accent out of nowhere seemingly for the sake of making his coworkers mildly uncomfortable. In the second episode, the Boss is seen walking around the hall while eating a plate of spaghetti, and in the following episode he casually mentions eating some of Alan's worms. In the Halloween special, he was among the many partygoers who assaulted the forest demon for "wearing blackface", feasting on one of its severed arms before tossing it into an indoor bonfire made from its brutalized remains. While facing competition from the Frowning Friends, he was driven "bonkers with jealousy", and consulted imaginary versions of Warren Buffett, Mr. Peanut, and Ronald Reagan for business advice. When that failed, he was reluctantly convinced to kill his competitors by an evil split personality. Despite his evident insanity, he is also shown to have a strong enough moral center to overcome his urges, quickly snapping out of his homicidal rage when Grim started crying for mercy.

Background
To be added

Charlie
Mr. Boss is Charlie's employer. They appear to be on fairly good terms, never being shown to quarrel.

Pim
Mr. Boss is Pim's employer. It's shown that Mr. Boss has a special level of trust for Pim, given the fact that he recruited him to pick up the firewood for the Halloween bonfire.

Alan
Mr. Boss is Alan's employer. They appear to be on fairly good terms, given the fact that they've never been shown to bicker.

Glep
Mr. Boss is Glep's employer. They appear to be on good terms, but this is hard to tell, given the fact that Glep speaks in his own language, never being shown to actually speak English until the end of Charlie Dies and Doesn't Come Back.

Boss Baby
He has a decent father-son relationship and openly feeds his baby when he feels like it.

Sightings
To be added

Voice

 * Marc M.

Debut

 * "Desmond's Big Day Out"

Quotes
"Don't. Go beyond the rickety bridge."

"Now get out there and make someone smile."

"Hey Charlie, the owner of the famous Salty's restaurant was just brutally murdered, and I need you and Pim to figure out who did it, thank you byeee."

"HEY."

"Relax, man. I was just gonna shoot you in the head and kill you."

"You should be happy your idea was so good that it drove me bonkers with jealousy."

Videos
To be added