When Billy decides he wants to grow up to be like Grim, he says nothing will stand in the way of their friendship. They meet a girl named Blandy, who looks very much like Billy, and Billy falls completely head-over-heels in love with her. When Blandy shows romantic interest in Grim, Billy is struck with mad jealousy and wants Grim out of the picture. Mandy consults Grim's encyclopaedia of monsters and realizes Blandy is actually a creature from another dimension. Despite Blandy showing her true form and leaving, Billy remains madly romantically infatuated with her; but only up until the following episode.

When Billy goes to visit his maternal grandmother and Mandy decides to have the day for herself, Grim finds himself free of the kids to do whatever he wants to do. Since Grim quickly gets bored he goes to visit General Skarr, and lets him take his magical scythe, which Skarr uses to build an army of giant lawn gnomes. Since Grim is so used to having two kids with him when they go on an adventure, he enlists Mindy and Pud'n to help him combat Skarr and retrieve his scythe. Mindy and Pud'n prove to be worthy substitutes but they are scared away by Mandy when she notices the unusual trio

When Billy digs his front yard he finds a frozen caveman, who is actually Fred Flintstone (from The Flintstones), but whom Billy names Jake Steele. Billy tries to acclimate Fred to the modern life but the job is not easy. When Fred is taken to school, he predictably goes out of control, kidnapping Miss Butterbean and running away in Principal Goodvibes' car. The ensuing chase results in Fred crashing into an ice cream truck, becoming frozen again. Instead of reaping him, Billy decides to bury Fred in the yard again. A future is shown where both Billy and Fred are defrosted by brain-eating creatures.

When Billy's dad gets a promotion at his job, he tells his family they are going to move to another town, starting a dispute between Billy and Mandy over who gets custody of Grim. Grim suggests they settle this in court, and hours later Billy, Mandy and Grim find themselves in the Underworld court, presided by Judge Roy Spleen, and which has Fred Fredburger, an incorrigible dumb character, as a juror.

Billy, Mandy and Grim visit Mighty Moe, an old man who has discovered the secret to add extra years to his lifespan: a good diet and exercise. Mighty Moe decides to publish his secret in a book, and Grim needs to stop him by offering junk food.

When Billy, Mandy and Grim go to the beach, Billy is swallowed by a whale known as Blubbery Joe, which also houses in her stomach Mister Geppetto and Pinocchio. Tired of not having a real son, Geppetto convinces Billy to be his "real son", while Pinocchio becomes increasingly jealous and is set on eating Billy's flesh to become a real boy and gain Geppetto's fatherly love and affection. Mandy and Grim search for Billy on board Captain Deadwood's ship, who is made of wood and who has been hunting Blubbery Joe for years. Billy, Geppetto and Pinocchio are expelled from Blubbery Joe's stomach, and as Billy needs to go home, Blubbery Joe accepts to be Geppetto's son.

When Billy and Irwin want to watch classic giant monsters movies, Grim decides to take them to Japan to see real monsters. They meet the turtle-like Cragorah (a parody of Gamera) who engages in a fierce battle with the three-headed Kittirah (a cat version of Ghidorah). To help Cragorah, Grim transforms Billy into a giant monster too (a parody of Ultraman). Mandy soon arrives with the intent of punishing them all for organizing this expedition without her permission. Controlling Mecha-Gorillasaur (a giant gorilla robot) she defeats Kittirah and beats Billy.

When Mandy and Grim go to the warehouse store, Mandy notices that everything seems to be in order, lacking any presence of chaos. Hoss Delgado, spectral exterminator, arrives saying that everything has been that way since he started dating Eris, the goddess of chaos. Mandy assures Delgado he must break up with Eris to restore chaos, but fearing her temper, he is reluctant to do so. After failed attempts by Grim, Mandy, Billy, and Irwin to break their relationship, Delgado finally tells Eris the truth about he wanting to break up, and she complies by turning into a giant insect and devouring him.

When General Skarr tries to get rid of a weed in his otherwise perfect garden, he asks Grim to use his scythe to do the job. Billy drives a lawnmower and ruins the garden; also, the scythe's magic accidentally shoots Skarr, transforming him into a plant-like creature. Using his new plant powers, Skarr rebuilds his garden, and tries to exact revenge on Billy by throwing a party, and attacking him. Skarr gets mulched by a helicopter rotor, but he is reborn as a small weed.

When Billy and Irwin are yet again bullied by Sperg, they decide to play for the school's football team so they are not bullied anymore. During practice, Irwin shows a powerful arm and he becomes the starting quarterback, while Billy is relegated to being a punching bag. During their first game, Mandy directs the team into scoring their first ever touchdown, so Coach Kilgore gives her the job of captain cheerleader, taking it away from Mindy. With Irwin's arm and Mandy's cheerleading the team reaches the finals. Mindy tries different ways to get back at Mandy and recover her job, but she ends up affecting her own team, which eventually loses the game.

When Mandy and Grim tell Billy to quit watching TV and follow his life dreams, Billy gets into a chicken costume and decides to become a world famous "chicken juggler". When Billy's mom tries to convince him to be a chiropractor instead, Billy runs away to Uncle Chokey's farm to pursue his dream. Billy and Uncle Chokey juggle chickens at the rhythm of an old phonograph, whose music turns the farm into a 1920s black and white rubber hose cartoon. Due to a shortage of eggs in the city, Mandy and Grim go to the farm to investigate. They destroy the phonograph and things return to normal.

When Billy gets his kite stuck in a tree, he starts throwing objects at it to knock it down, including Mandy and a group of three boy scouts, but all objects get stuck too. Frustrated, Billy and Grim call a druid for help, who in turn trains them to become druids, so the three of them can perform a ritual. Meanwhile, inside the tree, Mandy battles a group of squirrels, and leads the scouts back to the ground. Since the druidic chants did not work against the tree, the druid goes ahead and uses a chainsaw to bring the tree down, but this gets him arrested.

When Billy destroys Grim's favorite childhood toy, Fancy Jake, Grim feels devastated and wishes he had never lost the limbo game that made him become Billy and Mandy's best friend forever and ever. A lawyer appears saying that although the game is legally binding while all parties remain on Earth, it is not if Grim leaves Earth. In consequence, Grim follows the lawyer's advice, opens a mystical portal, and leaves. With Grim traveling aboard his spaceship, the lawyer takes off his disguise and introduces himself as Morg, the Martian Grim Reaper, who is also Emperor of Mars and commands an army of Martian, brain-eating zombies.

As Billy sees Hoss Delgado's manliness is action again, Billy wishes to grow up to be a hero like him. Grim tells Billy that in older times an evident way to become a hero was to slay a dragon. They travel to the Middle Ages so Billy can train under the supervision of the best dragon slayer, Sir Boss Del Guapo, who resembles the present time Delgado. Billy becomes friends with the dragon he was supposed to kill and spares his life, becoming the dragon's hero. Del Guapo finds himself transported to the present, where he has a brief encounter with Delgado.

As Billy and Mandy celebrate Father's Day, Grim becomes very depressed that he sits inside Billy's closet only listening to country rock music. Grim explains that, since his own father cared more about country rock than his own son, he has been living a lie; telling his father he is a famous country rock singer, and not the actual Grim Reaper. Mandy arranges for Grim's father to come visit and she tells him the truth, but still the old man does not believe her. Grim decides that the only way for his dad to listen to him is while performing country music. At an outdoor concert, Billy, Mandy, and Grim start performing a country rock song, in which eventually Grim reveals his supernatural abilities as the mighty Grim Reaper to his father. Grim's dad accepts his son is the Reaper, but he still does not forgive him for lying to him.

When Mandy says even a trained monkey is more competent to do cleaning chores than Grim, and would complain less, Grim makes Dickie Galoot, a monkey appearing in a Japanese-styled animation, come to life to prove her wrong. As Dickie turns out to be extremely good at cleaning Mandy's house, Grim decides to leave the kids for good. Due to his friendship contract, Grim is unable to break free, and he is forced to battle Dickie to recover his place as the "cleaning monkey" of the group. Grim successfully defeats Dickie at cleaning Billy's house, but this all turns out to be an ingenious plan devised by Mandy to win a bet against Billy.

When Billy finds his "son" Jeff the Spider lying in his bed with "Spider Pox", he goes to Mandy for help to get rid of the giant spider. While ignoring Billy, the next morning Mandy awakens afflicted by Spider Pox too, developing four additional arms and the ability to produce spider web. Mandy's condition progresses and she completely turns into a giant spider, who captures Billy's parents and Grim. Grim tells Billy that, to cure Mandy, he must use the venom of the spider that infected her. While Billy successfully gives Mandy Jeff's venom, he also carried the virus and infected the people of the city, who have all turned into spiders.

As Billy notices Mandy and Grim's usual negative attitude, he wishes they were in a magical land of happiness, so Grim transports them to an enchanted forest. Billy enjoys the relaxed surroundings until he meets a cantankerous and sour unicorn named Mary-Frances. Billy tries to change Mary-Frances attitude, but she is reluctant due to an earlier trauma of not being able to swim and follow the other unicorns into the sea. After Billy teaches Mary-Frances to swim, she feels happy and finally can join the other unicorns, but they turn out to be bullies, the real reason she never joined them in the first place. Billy stays with the unicorns and Mary-Frances goes back with Mandy and Grim to watch TV.

There is a new student in the school, named Dora (parodying Dora the Explorer), who insists on getting people to open her lunch box. Mandy befriends Dora once she gets into a fight with the snobby Mindy. While noting something strange with Dora, Grim does not recognize her as Pandora until it's too late and she tricks Mandy into opening Pandora's box, releasing all kinds of plagues upon humanity. Mandy restores everything to normal, and captures Pandora inside the box, saying that nobody tricks her, and that when the time is right it will be Mandy herself who will unleash humanity's doom and destruction.

When Grim decides to visit again his childhood idol, the aged king of the vampires, Dracula, the latter suggest they drive to an early bird buffet, only to get lost in the scorching desert. Grim and Dracula need to find their way back home while dealing with situations like meeting a creepy truck driver and being attacked by a giant scorpion. After what they have gone through, and thinking that Dracula is just a selfish, old man, Grim decides to go a separate way. After finding that Dracula in fact helped him by sucking out the scorpion's venom, Grim rushes to help Dracula, and they finally make it to the diner. However, it appears that Dracula left without paying the check.

As Mandy returns from Billy's house, it is evident that Mandy's parents are extremely afraid of their daughter and her iron fist rule over them. Unable to live in fear any longer, Mandy's parents call a nanny from a reality TV show who specializes in disciplining spoiled children. Mandy and the nanny clash while the nanny tries to teach Mandy's parents to show authority to control their daughter. Grim helps the nanny in her feud against Mandy by using his scythe to make Mandy's parents more controlling and resolute. Mandy quickly restores her tyrannic control over her parents, and shows the nanny she actually controls everything and everyone.

At a school fair, Grim's scythe accidentally transforms the dull Principal Goodvibes and his hippopotamus into gangster rappers, Goodvibes now calling himself Principal Goodbling. In the following, Goodbling changes the entire school to be more hip-hop-oriented, to the annoyance of Mandy. Although initially Grim likes the new style of the school principal, he later thinks Goodbling is just a poseur and goes to talk to him, but Goodbling attacks with yo-mama jokes. Irwin's grandmother, Tanya, confronts Goodbling and proves to be better than he is at yo-mama jokes that Goodbling reverts to being the boring Goodvibes.

As Grim appears in an Underworld TV commercial for "Big Move" laxative pills, an accompanying contest promises a day with the famous Grim Reaper to the monster who writes the best 500-word-or-less essay describing the fun things they would do. It turns out the winner of the contest, and sole participant, is the dimwitted Fred Fredburger, who only wants to eat frozen yogurt. The Big Move company blames Grim for their sales going down since they hired him. In consequence, Grim tries save his reputation and make the best day for Fred, but it is a disaster with Grim ruining Fred's yogurt and Fred going missing in an amusement park. The Big Move executives give Grim a beating for ruining their company, and Fred finds his own paradise in a cold place with nachos- and frozen yogurt-loving creatures.

As Billy, Mandy, Grim, and Irwin hang from a rope about to be eaten by a giant sea serpent, Irwin wonders how they came into that trouble. Billy and Grim each tell separate stories on how they originally became best friends forever and ever. Billy's fantastic story is about him and Mandy being space patrol officers who collect the Grim Reaper's bones, cloak, and skull to summon him; Grim tells a story on how the evil Mandy and his pet servant Billy managed to capture him inside a containment unit (parodying the Ghostbusters' ghost traps). Mandy quickly tells the real story, and footage from the first episode is seen, before the four are swallowed whole by the serpent.