Frank and Len are writing a rock opera for everyone in the house to star in at the Gloomsville Music Hall. But they experience writer's block and just can't seem to get a handle on the opera's four star characters: Misery, Iris, Doom, and Ruby. Ruby suggests they just need to imagine what its like to be them. You know "get inside their head" more. Frank and Len try this to no avail. But when they slip and bump their heads – they wake up…inside...

When Doom's odd behavior includes pointing to things that aren't there, Ruby starts to worry she's having a nervous breakdown. The gang tries to set Doom on the right course but it turns out, Doom's not bonkers at all. She's just been seeing a ghost-in-training, "Boo-Boo" who is trying to win favor from his "Family" (two ghost gangsters both named Mr. White). Problem is, Boo-Boo can't scare a soul and Doom can't prove there's a ghost in the house...

The gang is shocked to discover that Scaredy Bat has never actually flown due to nerves and a "woozy" reaction to heights. Ruby takes the lead as they try to help him conquer his fear. But it's not until Scaredy Bat finds a good reason to fly that he actually learns he can – when his friend Ruby is in danger and he has to save her.

The whole house is a hive of activity as everyone prepares for the upcoming science fair. Skull Boy is distraught because he can't seem to come up with an idea for a project. With Poe's help, Skull Boy gets the idea that he should build a father to help with his science fair. After some failed father-son activities, Skull Boy soon realizes that his new dad may do more harm than good. His creation must be stopped before a rampage threatens to destroy...

When Skull Boy thinks he's a descendent of Shakespeare, he spouts his own love sonnets making Iris and Misery instantly crush on him. Skull Boy is embarrassed by the attention (and stalking) and gets Ruby to help him be "less attractive" to the girls. But Iris and Misery misinterpret all this time Ruby and Skull Boy are spending together as "loooove" so think Skull Boy must like the "Ruby type" better. Soon, they dress and act like Ruby and before...

When Poe injures his wing, he is soon driving everyone crazy with his incessant demands. Ruby relegates Poe to the highest turret in the house to rest and recuperate (and to preserve everyone else's sanity). In an homage to Rear Window, Poe soon misinterprets the actions of their new neighbor, convinced he is up to something sinister. His suspicions grow to panic as he watches Iris, Skull Boy and the rest of his friends one by one go next door....

Ruby plans a surprise party for everyone but due to a series of mishaps and broken telephone, everyone gets the wrong impression that Ruby's moving out. They plot various ways to make her stay not the least of which is Misery acting "happy" (result: disaster). Meanwhile, Frank and Len actually think Ruby is dying and do everything they can to console her during the inevitable "5 stages of death".

It's the 7th anniversary of the Day Misery Was Rescued from an Ice Floe and Ruby wants to make it extra special. She invites Misery's cousins, Malady and Malaise to join the festivities. The longer they stay however, the colder the house gets, until it completely freezes over. Misery reveals the only way to de-ice the situation is to separate Malady and Malaise. Poe and Iris take on the responsibility of entertaining the morose sisters and the de-icing...

Scaredy Bat is terrified at the prospect of losing his wisdom tooth for fear of losing all his wisdom. He's even more terrified of a scary tooth fairy coming in the night to snatch his tooth. The gang try to convince him things will be okay, and try helping him get rid of the aching tooth. Finally, the tooth comes out and Scaredy is nervous to go to sleep. The tooth fairy does visit that night – but turns out, she's more timid than he is and...

Once in a blue moon the dreaded Luna Monster appears and tonight is the night. A brave Ruby convinces her friends to camp out in the backyard in order to catch a glimpse of the legendary creature. However, she quickly loses her nerve and bolts for the house when the gang sitting around the campfire, shares stories about the scary monster. Iris, Misery, Skull Boy and Scaredy Bat convince her to come out of the house and overcome her fear. But will...