| No.overall | No. inseason | Title | Directed by | Storyboarded by | Original release date | US viewers(millions) |
| 10 | 1 | "Gwimbly: Definitive Remastered Enhanced Extended Edition DX 4K (Anniversary Director's Cut)" | Paul ter Voorde | James Cunningham, Michael Cusack, Michael Dockery & Zach Hadel | April 1, 2024 (2024-04-01) | 0.13 |
| 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 to crowdfund 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 a fentanyl 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 a Super Smash Bros.-esque crossover fighting game, with Mr. Boss also joining as a playable character. Post-credits scene : James drunkenly expresses remorse for how he treated Charlie, believing Charlie to be the only person who truly cared about him. |
| 11 | 2 | "Mr. President" | Tina Tomar | Michael Cusack, Michael Dockery & Zach Hadel | May 13, 2024 (2024-05-13) | 0.28 |
| Pim and Charlie get a call from the concurrently running and very unpopular President 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 a foreign policy with an infamous dictator that has committed genocide against an entire race of people. While walking out in frustration, Charlie accidentally discovers a secret society of worms in the White House basement that are trying to sabotage the vote in favor of Mr. Frog, but accidentally persuades them into supporting Jimble instead upon revealing that frogs eat worms. At the Presidential 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 causes Mr. Frog to win the election anyway via the electoral vote. Glep is doxxed by the news as he is angrily confronted by his friends, but they change their minds after his unintelligible explanation. Post-credits scene : Jimble relaxes at a beach and enjoys retirement, taking advice Charlie had given him earlier in the episode. |
| 12 | 3 | "A Allan Adventure" | Paul ter Voorde | Michael Dockery, Jake Ganz, Paul Georghiou, Paul ter Voorde & Sheldon Vella | May 20, 2024 (2024-05-20) | 0.18 |
| Mr. Boss tasks Allan with buying more paperclips 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, a helicopter chase with the U.S. Air Force, a Sasquatch, a crew of undead pirates, and finally a massive leviathan that swallows Allan and ejects him from its blowhole. He washes ashore with the box of paperclips, but opens it to find it empty aside from a ransom 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 playing Burnout: 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 commits seppuku. 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. Post-credits scene : The landlord resurrects in a morgue, swearing that Allan will hang out with him again. |
| 13 | 4 | "Erm, the Boss Finds Love?" | David Hootselle & Anthony Price | Michael Dockery, Paul Georghiou & David Hootselle | May 27, 2024 (2024-05-27) | 0.28 |
| After Mr. Boss marries a malformed succubus 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 own rose bush. Mr. Boss thanks them for freeing him and declares that his true love is his work before singing to the four uncomfortable employees. Post-credits scene : Mr. Boss (who obtained 25% of Hell following Brittney's death) and Satan argue over fence line property boundaries. Note: Doug Walker makes a cameo appearance in this episode, portraying a parody of his Nostalgia Critic persona; a demonology-focused YouTuber whose videos Pim, Charlie, and Allan consult for information. |
| 14 | 5 | "Brother's Egg" | Anthony Price | Tijmen Raasveld & Jakub Zieba | June 3, 2024 (2024-06-03) | 0.20 |
| Pim and Charlie are called to help aspiring mad 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 to painkillers and not being present for their mother, leading up to her death. One of Daniel's eggs then hatches, revealing a homunculus 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. Post-credits scene : Allan cries over a film that is also about estranged brothers reconciling, despite disliking it before Pim and Charlie's departure. In contrast, Mr. Boss cries over his inability to revert his face to normal after he had changed it into a dog's face earlier. |
| 15 | 6 | "Charlie, Pim, and Bill vs the Alien" | David Hootselle | David Hootselle | June 10, 2024 (2024-06-10) | 0.17 |
| Pim takes Charlie to his UFO sighting group – Bill, Duncan, and Fillmore (David Firth). The meeting proves uneventful until a UFO arrives and abducts Pim, Charlie, and Bill – the latter of whom is dissected and eaten. The aliens 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 for destroying public property and disturbing the peace. As the partygoers flee, Pim and Charlie manage to hijack a flying saucer owned by the grey aliens and fly back to Earth, which they discover is flat and encased in a glass dome. Post-credits scene : Duncan and Fillmore have been falsely imprisoned for Bill's murder and Charlie and Pim's disappearances. Note: The official description for the episode is intentionally false, describing Pim in the plot of Mars Needs Moms. |
| 16 | 7 | "The Magical Red Jewel (aka Tyler Gets Fired)" | Jeff Liu | Max Collins, Tijmen Raasveld & James White | June 17, 2024 (2024-06-17) | 0.27 |
| 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 childhood pen 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 into anarchy. Meanwhile, Mr. Boss has tasked Allan, Glep, and Charlie with babysitting his teenage son Jason, but Jason inexplicably dies shortly after Mr. Boss and Pim leave. Mr. Boss is initially horrified, but uses the jewel to resurrect Jason, who sprouts butterfly wings. Charlie attempts to inquire about a manifesto 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 Jason lunges at the audience. Post-credits scene : Tyler, while at a bar with Charlie, resolves to focus on a music career instead of returning to Smiling Friends. |
| 17 | 8 | "Pim Finally Turns Green" | Paul Georghiou | Paul Georghiou & Michael Cusack | June 24, 2024 (2024-06-24) | 0.21 |
| The Friends build a snowman 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 an existential crisis and starts screaming uncontrollably. Charlie enlists Bill Nye to teach Rotten that death is natural and not something to fear, but Nye dies when his hot 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 frustrated yeti. 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. Post-credits scene : The Friends question the logistics of Rotten's new state of being before he consumes a boat and sends a tsunami towards the shoreline as horrified beachgoers evacuate. Note: The title and official description for the episode are intentionally false; the description states: "After eating a mysterious artifact found at an ancient burial ground, Pim suddenly and mysteriously turns bright green to everyone's dismay." |
