• Adultanimated sitcom
• Black comedy^[1]
• Surreal comedy^[2]

• Zach Hadel
• Michael Cusack

• Michael Cusack
• Zach Hadel

• Michael Cusack
• Zach Hadel
• David Hootselle (episode director; season 3)

• Michael Cusack
• Zach Hadel
• Marc M.

• Australia
• United States

• Michael Cusack
• Zach Hadel
• Mike Cowap
• Emma Fitzsimons
• Brendan Burch (2020)
• Keith Crofford^[a] (2020)
• Walter Newman^[a]
  (2020–22)
• Ollie Green^[a] (2022)
• Kelly Crews^[a]
  (2024–present)
• Cameron Tang^[a]
  (2024–present)

• Scott Malchus
• Ollie Green
• Laura DiMaio
• Paul Moran
• Casey Rup
• Cody DeMatteis

• Scott Henry
• Lukas Xuereb
• Aron Fromm

• Goblin Caught on Tape
• Williams Street

While getting dinner at the popular fast food restaurant Salty's, Pim and Charlie find founder Simon S. Salty dead in a back room. They call the police, who explain that the murder investigation division was moved to a separate company due to budget cuts; Mr. Boss then calls and informs them that the Smiling Friends are in fact the police's new division. They interrogate Salty's team of living mascots, all of whom display alarmingly unhinged behavior. They eventually recover security footage from the discontinued "century egg" mascot that reveals that Salty had ultimately died of aheart attack from his own unhealthy diet (ironically, after eating what he swore would be his last burger before changing his lifelong eating habits), but that all of his mascots later separately attempted to kill him for their own reasons, unaware that they were attacking a corpse. Gleefully after they are declared innocent, the mascots leave the restaurant and immediately begin to wreak havoc in public.

While on a mission to help the princess of the nearbyEnchanted Forest smile for a portrait, Pim and Charlie get sidetracked by ahobbit-like forest dweller named Mip. Charlie undertakes several quests despite his earlier apathy towards doing so, causing Pim, who wanted to do the quests beforehand, to accidentally kill Mip in a jealousGollum-esque struggle. Remorseful, he and Charlie give the princess the gift Mip had intended for her, but she reveals that Mip was her stalker; inside the box is a bomb, which she frantically discards in a panic before finally smiling upon learning of his demise, much to the duo's confusion.

Pim and Allan try to help washed-up video game mascot Gwimbly after he ends up on the company's doorstep by getting his parent company to make him a new game. When the CEO refuses, they decide tocrowdfund the game themselves, leaving him enraged that they are using his intellectual property without permission. As he hunts them with the company's new mascot, Troglor, the trio discovers that Gwimbly's ex-nemesis is busy with his family life and his sidekick has died of afentanyl overdose. Meanwhile, a violent, burly man named James breaks into the Smiling Friends' office. He forces Charlie to do increasingly degrading things to (unsuccessfully) make him smile, culminating in him tearing Charlie's nose off. The CEO chases Pim, Allan, and Gwimbly into the office, where James stabs the CEO to death; satisfied by this, he finally smiles and leaves. Gwimbly and Troglor later join aSuper Smash Bros.-esque crossover fighting game, with Mr. Boss also joining as a playable character.

Pim and Charlie get a call from the concurrently running and very unpopularPresident of the United States, the unhygienic and unintelligent Jimble (Mike Bocchetti), requesting help in winning the upcoming election. He is struggling to run against his rival Squiggly Miggly as well as the sudden nomination of Mr. Frog, who gains countrywide support despite him openly reveling in extremely violent behavior. Their attempts at earning him a higher approval rating fail as Jimble soils himself during a speech, inadvertently crashes the economy trying to make everyone rich, and establishes aforeign policy with an infamousdictator that has committedgenocide against anentire race of people. While walking out in frustration, Charlie accidentally discovers a secret society of worms in theWhite House basement that are trying tosabotage the vote in favor of Mr. Frog, but accidentally persuades them into supporting Jimble instead upon revealing that frogs eat worms. At thePresidential Debate, a despondent Jimble admits that he was utterly incompetent as President and expresses remorse, swinging public favor in his direction. However, a single vote submitted by Glep inPennsylvania causes Mr. Frog to win the election anyway via theelectoral vote. Glep is doxxed by the news as he is angrily confronted by his friends, but they change their mind after his unintelligible explanation.

Mr. Boss tasks Allan with buying morepaperclips for the office. Allan obtains them from an electronics store, but is faced with various obstacles and misadventures before he can make it back to the office - namely a thief, ahelicopter chase with theU.S. Air Force, aSasquatch, a crew ofundead pirates, and finally a massiveleviathan that swallows Allan and ejects him from itsblowhole. He washes ashore with the box of paperclips, but opens it to find it empty aside from aransom note telling him to retrieve the paperclips from his own apartment complex. There, he meets his landlord, who reveals he orchestrated the entire escapade to get Allan to spend time playingBurnout: Revenge with him, threatening to detonate a bomb that will ravage the entire city if he refuses. Allan reluctantly complies before using a paperclip to defuse the bomb. Ashamed at having been outsmarted, the landlord commitsseppuku. Allan returns to the office with the paperclips and is rewarded with a miniature figurine of Mr. Boss. Uninterested in keeping it, he gives it to Charlie instead.

After Mr. Boss marries a malformedsuccubus named Brittney, the company undergoes a complete rebrand under her influence. Suspecting Brittney of having sinister intentions, Pim, Charlie, and Allan do more research and learn that "Brittney" is actually Filia Diabolus, the daughter of Satan who manifests every 100 years to kill influential men and grant their belongings to her father, and that the only way to defeat her is to kill her during a full moon. Since the moon is full that night, they race to Brittney's castle (except for Allan, who leaves for an appointment with a "Doctor Monster"). Pim's attempt to stab her in her sleep fails when the knife Charlie had drunkenly purchased from a fellow wedding attendee turns out to be a prop knife. Still, she wakes up and becomes so distraught upon learning of their intentions to kill her (though admits that their assumptions were correct) that she jumps out a window, becoming fatally impaled by her ownrose bush. Mr. Boss thanks them for freeing him and declares that his true love is his work before singing to the four uncomfortable employees.

Pim and Charlie are called to help aspiringmad scientist Daniel "Professor Psychotic" create life. As Daniel explains his plan, his older brother Doug (Joel Haver) enters to complain about his lack of volume control and inability to find a proper job, ultimately evicting him. Charlie has lunch with Daniel to console him and help him find a new purpose in life, but the effort is unsuccessful as Daniel unintentionally scares away a female waiter. Meanwhile, Pim visits Doug at his job at a construction site to convince him to give Daniel another chance, and is successful after they witness Doug's coworker mourn his estranged brother being crushed to death. Pim and Charlie mediate an intervention between the brothers, which devolves into a physical altercation after Daniel accuses Doug of being addicted topainkillers and not being present for their mother, leading up to her death. One of Daniel's eggs then hatches, revealing ahomunculus who implores the brothers to stop fighting. Astounded by this discovery, the brothers resolve to put aside their differences and raise the homunculus together before sharing a tearful embrace.

Pim takes Charlie to hisUFO sighting group – Bill, Duncan, and Fillmore (David Firth). The meeting proves uneventful until a UFO arrives andabducts Pim, Charlie, and Bill – the latter of whom is dissected and eaten. Thealiens that abducted the trio are then abducted by a different alien race, who are hosting a party that Pim and Charlie unwillingly participate in. The hosts (Mike Stoklasa and Rich Evans) implore Pim and Charlie to vaporize a populated planet as a "prank", promising to take them home if they do and threatening to place them in an eternal torture chamber if they refuse. They reluctantly comply, only for the aliens to reveal that the planet was devoid of life, the torture device was fake, and the ship can't fly backwards, rendering them unable to return home. During the ensuing argument between Charlie and the aliens, the police arrive to arrest them fordestroying public property anddisturbing the peace. As the partygoers flee, Pim and Charlie manage to hijack aflying saucer owned by the grey aliens and fly back to Earth, which they discover isflat and encased in a glass dome.

After firing an employee named Tyler, Mr. Boss informs the Friends that he must journey to the foreign country Spamtopia to purchase a magical red jewel. Pim accompanies him, as he speaks the local language, Spamish, having learned from his childhoodpen pal Oscar. While obtaining the jewel from the elusive "Mr. Jester", Pim accidentally breaks Spamtopia's sole law by making eye contact with Mr. Jester, who, revealing himself to be the ruler of Spamtopia, sentences the two to death. However, he turns out to be Oscar and spares them after remembering Pim, ultimately eschewing the law entirely; Spamtopia thus descends intoanarchy. Meanwhile, Mr. Boss has tasked Allan, Glep, and Charlie with babysitting his teenage son Jason, but Jasoninexplicably dies shortly after Mr. Boss and Pim leave. Mr. Boss is initially horrified, but uses the jewel to resurrect Jason, who sproutsbutterfly wings. Charlie attempts to inquire about amanifesto he found hidden in Mr. Boss's desk. Still, the glittery dust spread by Jason deafens and blinds everyone whilst triggering the building's alarms and sprinklers before Jasonlunges at the audience.

The Friends build asnowman out of garbage, naming it Rotten (Dana Snyder). Rotten comes to life after Pim attaches a radioactive daffodil to its head, and Pim decides to teach him about the pleasures of life. Pim denies Rotten's request to visit the beach, claiming the sun will kill him; horrified at the concept of death, Rotten suffers anexistential crisis and starts screaming uncontrollably. Charlie enlistsBill Nye to teach Rotten that death is natural and not something to fear, but Nye dies when hishot air balloon flies into power lines. Pim and Charlie leave Rotten on a snowy mountain so he can live forever, but he is returned to the office by a frustratedyeti. Glep suggests storing Rotten in the office freezer, which initially leaves him content, but as time passes, he becomes depressed. As the Friends leave for a trip to the beach, Pim realizes he can take Rotten by putting him inside a cooler, but he melts when another beachgoer accidentally knocks it over. As they mourn him, he suddenly reappears as an ocean wave, along with the ghost of Bill Nye.

The Smiling Friends get a call from a ridiculous-looking man named Silly Samuel (Conner O'Malley), who is upset that no one takes him seriously due to his bizarre appearance. Pim and Charlie's various attempts to help him fail, as his physique renders him unable to wear clothes, get plastic surgery, or even remotely alter his body without fatal consequences, and he is unwilling to embrace his nature to become a circus performer. Meanwhile, a building inspector performs a surprise inspection of the Smiling Friends office, during which a nail keeping the building in place is released, causing it to roll down the street toward a nearby park full of onlookers laughing at Silly Samuel. He attempts to warn them while also berating them with truthful yet controversial statements about other topics. Glep stops the building before it crushes anyone; realizing that he was telling the truth, the onlookers label Silly Samuel a "prophet" and carry him off as he smiles. The building inspector thanks Mr. Boss for entertaining him despite the building's abysmal quality before turning into dust.

After Mr. Frog assimilates the entire planet under his leadership, he finds himself dissatisfied and resigns from his new role as "emperor of earth", declaring a discarded peanut as his successor. Pim and Charlie find him depressed in a bar and offer to help him smile again. Frog joins theUltimate Fighting Championship, where he kills all of his opponents with sheer durability despite not even trying to fight back. After Pim mentions family in a song about life's pleasures, Frog travels to his father's (Creed Bratton) cabin. Frog's father reveals that Frog's mother has recently died of cancer, then berates Frog for his psychopathic behavior and abandonment of his family, ultimately disowning and ejecting him. While meditating in the forest, Frog achieves inner peace and subsequently enters a realm where he meets the "Bug of Knowledge". After eating the bug, Frog experiences a series of visions highlighting significant moments in his life and career. Content, he transforms into a photorealistic frog, smiles, and says, "Goodbye."

Pim and Charlie fall through asinkhole in the office and become trapped in the lair of Mole Man, an anthropomorphicnaked mole-rat who has become obsessed with the duo after overhearing their banter over the years. Mole Man prods the duo to compliment his penis, which he is deeply insecure about. Charlie refuses, causing a hysterical Mole Man to chase them through a series of underground tunnels. Meanwhile, Mr. Boss christens Glep and Allan the "new Smiling Friends" upon learning that Pim and Charlie likely did not survive the fall, and sends them to help a single mother, Maurine, with her triplets. The children wreak havoc until Pim, Charlie, and Mole Man emerge from a vent in Maurine's house as she returns. Mole Man inadvertently exposes himself to her, but she finds his penis attractive. He agrees to marry her and stepfather her children, renouncing his obsession with the Smiling Friends, who agree that Mole Man's penis is rather unassuming and not "disgusting" as he had led them to believe.

The Friends contemplate what to order for lunch, repeatedly ignoring Pim when he suggests pizza. A mysterious green-skinned witch then arrives at the office asking for change. Pim tries to give it to her, but the other Friends refuse, and she curses them. The power then goes out, and the Friends undergo some disturbing changes - Glep is possessed, Charlie melts, Allan turns into a spider, and Mr. Boss is taunted by an apparition of his deceased mother. Encouraged by demons who insist that the others do not respect him, Pim goes into a blind rage and murders the Friends. This is all then revealed to be a vision the witch is showing them from her orb to demonstrate what will happen if they do not give her money. Mr. Boss chokes her, and Charlie apologizes to Pim for his earlier behavior. Spider Allan returns with pizza, to the confusion of regular Allan and the others, only for him and Mr. Boss to be run over by cars.

While vacationing at Mr. Boss's remote cabin, Charlie hopes to get a valuable photograph of the legendary "Brown Blur" cryptid Mr. Boss has a painting of. He and Pim instead encounterMoth Man (Jim Norton), and an anthropomorphizedMother Nature who is upset when Charlie throws an empty soda can onto the ground. They blame the littering on Moth Man, then clean up the various trash hikers have left in the forest. Mother Nature thanks them for restoring her to health before fatally crushing Moth Man under a tree as revenge for littering. Amushroom overhears Pim scolding Charlie and informs Mother Nature, who then furiously attacks and tries to eat Charlie. Meanwhile, Mr. Boss tries to convince Allan to relax and stop thinking about work, leading to a tryst between the two. Realizing that Allan, Mr. Boss, and Glep will not save them, Pim throws the soda can into Mother Nature's mouth, killing her. Pim and Charlie return to the cabin, where Mr. Boss reveals that the "Brown Blur" painting was actually a photograph of the inside of his anus during acolonoscopy.

When Charlie feigns illness to skip work and play a new video game and Allan and Glep travel to ananime convention, Mr. Boss rehires Squim, the "first-ever Smiling Friend," to help Pim with a job. Although Pim innitially enjoys Squim's positivity, he becomes annoyed when Squim inappropriately attempts to cheer up an ice cream man mourning his late wife. Meanwhile, Mr. Boss views Charlie's Steam activity, berates him on the phone for lying, and threatens to fire him if he does not arrive by noon. On the bus, Charlie actually falls ill and vomits, causing the bus to crash. He deliriously stumbles toward the office, causing traffic collisions and eventually stripping naked. As police surround him, Squim attempts to de-escalate the situation by dancing and is shot. His soul emerges from his body and continues dancing, but is also shot. In the hospital, a doctor informs Charlie that he was infected by aparasite in akebab he ate earlier. Mr. Boss commends Charlie's loyalty to him and reveals that Squim's soul survived after surgery.

Pim and Charlie are called to help a kingdom of happy creatures called the Shmaloogles, though Charlie immediately attempts to leave. As he does, Pim and a Shamloogle are kidnapped by a wizard: an occurrence the Shmaloogles are unfazed by until Charlie rallies them to seek retribution. The wizard confides to Pim that he isbalding and uses the Shmaloogles' blood to prevent further hair loss: hence why he kidnaps them. Charlie and the Shmaloogles swarm the castle and subdues the wizard, prompting Pim to reveal the reason he was kidnapping them. Charlie suggests an over-the-counter medication which he claims has worked for him in the past, which the Wizard claims he will try to use in the future. While atWawa, the King of the Shmaloogles mentions that he saw Charlie take a photo up Princess Shmaloogle's skirt during the castle raid, though Charlie angrily swears his innocence, pointing out that he has not had access to his phone all day.