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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.
While traipsing in a snooty Nob Hill area, Charlie and Itchy are lured into a trap set by a bratty dog-hating kid named Teddy.
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.
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.
Itchy becomes infatuated with a pedigree named Bess, who, through a number of miscommunications, thinks it's Charlie who likes her.
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.
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.
Bess and Sasha plan a double date with Charlie and Itchy, unaware that the bickering buddies have had their personality souls swapped by Annabelle.
Sasha visits her sister and her new puppies in Los Angeles, leaving Charlie and Itchy in charge of the Flea Bite until she returns.
Charlie auditions to be the new spokes-dog for Gulpo Dog Food, but the company picks Itchy instead. Now Itchy's famous and Charlie's left sulking in the Flea Bite Café, leaving everyone wondering, 'Will success spoil Itchy Itchiford?'
Annabelle assigns the duo on a mission to help a boy named Leon join his Little League team. What Charlie doesn't know is that this is Itchy's twentieth mission, and if successful, he will be reallowed entry to Heaven. With the separation between him and his best friend at stake, Charlie struggles with moral dilemma: to deliberately tank the mission or help out and let Itchy go back to Heaven.
Sasha wants a 'perfect dog' and Charlie takes advantage of being hit by a car to smother her in love and kindness, until she goes mad.
