Smiling Friends - Characters & Cast

Driven by an innate, almost pathological need to validate his own happiness by making others smile, often at the expense of his own safety.

Pim begins as a purely manic source of positivity. Over three seasons, he undergoes a sobering transformation as his idealism is repeatedly crushed by the world's cruelty. By the end of Season 3, he remains optimistic but gains a more grounded, weary understanding of his mission's difficulty.

Initially motivated by personal comfort and avoiding conflict, his drive evolves into a genuine, if begrudging, commitment to the well-being of his colleagues.

Charlie's development is defined by his literal brush with death and subsequent trip to Hell in Season 1. This experience gradually moves him from a position of lazy apathy to a more active, protective role within the company, eventually seeing him face existential dread in Season 3 with a newfound sense of loyalty to his friends.

Maintaining his empire of smiles through whatever surreal or unethical means necessary, fueled by a warped sense of love and control.

Moving from a background figure to a central catalyst for chaos, Mr. Boss is revealed to be far more than a simple businessman. His arc reveals a history of demonic marriages and secret society involvements, ultimately showing him as a dangerously insane but oddly paternal figure to the team.

The pursuit of order and personal satisfaction, often finding himself forced into heroic roles despite his desire for a simple, quiet life.

Allan evolves from an office manager obsessed with cheese and paperclips into a highly capable action hero. His solo adventures in Season 2 and Season 3 showcase his hidden competence, proving he is the structural glue that keeps the company from falling into total madness.

Contentment with small pleasures (iPad games, snacks) while secretly carrying the weight of centuries of experience and history.

Long viewed as a background joke, Glep's arc culminates in the Season 3 finale, "The Glep Ep." It is revealed that Glep is an immortal being nearly 1,700 years old who influenced world history and co-founded the Smiling Friends after saving Mr. Boss's life in the 1990s.