Itchy gets sent to the pound and has to break out with help from Killer.

For having messed up three missions in a row, Charlie's put on probation by Annabelle so isn't allowed to do, say, or even think anything bad until he does a good deed. When Carface and Killer take over the Flea Bite Café and turn it into an arcade, Charlie and Itchy have to cross-dress to get the café back.

Charlie is put on Heavenly Trial by Belladonna, who alleges that he's been abusing his angelic position. If found guilty, Charlie will be stripped of his duties and sent to work on the other side.

Charlie recounts how he met Itchy, and how he'd been a bad dog to a pair of puppies arguing over a bag of dog food.

Itchy accompanies Bess to her dog school reunion, with Itchy pretending to be of pedigree. Afghan Hound Tiffany humiliates Bess, sparking Charlie to prank her, but it only makes everything worse. After Tiffany puts fleas on Itchy, the beam she's standing on collapses. With the other dogs unwilling to help, it's Itchy to the rescue.

Charlie decides to try Kibbleland's new game, but he becomes selfish to not only think of himself and nobody else, not even Sasha. This becomes serious when Belladonna tricks Sasha into playing the game as a big tornado approaches and sucks her into the world of Kibbleland. The duo must find a way to rescue her before she's trapped forever.

Bess is being threatened by her ex Manfred and wants out to be with Itchy. Itchy tries everything to protect her but it's Charlie who saves Bess. Itchy is later hypnotized by a magician who turns him into a superhero.

Charlie and Itchy are sent on a seemingly nefarious mission, unaware that who they believe is Annabelle is in fact her demonic cousin Belladonna.

Bess and Sasha plan a double date with Charlie and Itchy, unaware that the bickering buddies have had their personality souls swapped by Annabelle.

Carface and Killer steal Itchy's Heavenly Collar, so Charlie, Itchy, and Sasha plan to get it back. When the plan involves Sasha flirting with Carface, Charlie's jealousy gets the better of him.

Itchy becomes infatuated with a pedigree named Bess, who, through a number of miscommunications, thinks it's Charlie who likes her.

Itchy is unable to properly beg for food, unlike Charlie, who masters it quite often. Under Charlie's guidance, Itchy begs a spoiled rich girl for ice cream, who, in return, takes Itchy as a new pet. Meanwhile, Carface and Killer have picked the same house as their next target in a string of burglaries.

Charlie becomes obsessed with being recorded doing a heroic act. That is, until Itchy almost drowns, but the reporters catch him saving Itchy, and the two get to go to an exclusive hotel suite.

Itchy is frightened by a wilderness movie, but Charlie tells Itchy that every dog has wolf blood in them, even Itchy. And so Charlie decides that they are going on a trip into the wild, so Itchy can live up to his heritage. They encounter a lost girl scout named Charlotte, and help her find her troop.

Itchy and Charlie write a report for David on the history of all dogs and how they helped society.

Itchy gets so scared that he can't help Charlie, who decides it's time for Itchy to face his fears. He tells Itchy that they are spending the night in a supposedly haunted mansion, unaware that it's not just superstition.

It's David's 10th birthday and he's received a voice recorder. However, it gets him study hall from the vice principal, so Charlie and Itchy bust him out for a day of fun but must watch the clock to get their human friend back in time.

Charlie needs a vacation, and manages to convince Itchy into taking one, but with so many bad things happening, Charlie can't even go a block without being someone's Guardian Angel.

Itchy tells the story of the amazing Double Dog Dare and how he saved the world.

A new, rule-abiding canine named Lance the Wonder Pup arrives from Heaven, only bringing headaches to those around him.

Anabelle assigns Charlie and Itchy to find a home for a little puppy. The puppy turns out to be extremely wild and impossible to find a home. Charlie, however, discovers that Sasha is impressed with his nobility he is when caring for the pup.

A magic multiplying box spells three times the trouble when Charlie overbooks his afternoon between a date with Sasha, his poker buddies, and a fight with Otto and his gang.

Charlie volunteers to go get notes that David's crush Alex left in her mom's car, but Sasha must go with Charlie instead. Charlie, however, doesn't see women as good partners for this type of thing. Sasha decides to show Charlie what women can do.

Charlie and Itchy are sent to a military base and show a kid how to have fun, but Anabelle also sent them there so Charlie would learn some respect for authority figures.