[[WMG: When Itchy died between the first and second movie, he went through a time warp]]
Think about it. Dogs live about 10 to 20 human years on average, and both Charlie and Itchy are 25 in dog years. Itchy died from choking on a piece of chicken, and the first movie took place in 1939, while the second took place in 1996, the year of its release.
* Or Carface went through a time warp when he left, or there was a massive TimeSkip in the second movie.
* Perhaps Charlie and Carface's short trips back to earth caused chaos in Heaven's bureaucracy and held up a bunch of dogs for several years?

[[WMG: Carface's time in heaven between films is responsible for his VillainDecay]]
Spending so long in Heaven between films softened him a bit. He wasn't a good guy, but wasn't a threat like before. Worked for Dabura in ''Anime/DragonBallZ'' and he was a demon king, makes more sense here to. Also, this would help explain his [[spoiler: HeelFaceTurn in the ChristmasSpecial]].

[[WMG: Anabelle managed to convince Carface not to return to Earth]]
He's last seen preparing to steal his life clock at the end of the first film, Anabelle convinced him not to.
** She's last seen ''chasing after him'' and screaming "I SAID, YOU CAN ''NEVER'' GO BACK!!" In this case, "convince" equals "force."

[[WMG: Belladonna freed Carface from Hell as part of a DealWithTheDevil]]
Whenever Belladonna shows up, Carface works for her. It's never explained how he got out of Hell after Red dragged him there. Belladonna probably freed him in exchange for his service, she just didn't call in the favor until she finally showed up herself. When he performed his HeelFaceTurn and redeemed himself, it got him out of the deal.
* It all makes sense: to Carface, a crime lord and ruthless gambler, selling his soul to Red in exchange for life of servitude was "strictly business" and he had no idea [[NotWhatISignedOnFor he was getting more than he bargained for]]. He agrees to work for Belladonna because he assumes he'll suffer significant less as ''her'' lackie, but come the Christmas special, he sees that [[MyGodWhatHaveIDone he just made the same mistake again]] and all the years of serving demons have frightened him out of being a criminal, as [[EveryoneHasStandards he knows what]] ''[[EveryoneHasStandards true]]'' [[EveryoneHasStandards evil is]] and decided to become a better person for it. Kind of makes his VillainDecay more like CharacterDevelopment, doesn't it?

[[WMG: Charlie is a reincarnation of Rocky Sullivan from the movie ''Film/AngelsWithDirtyFaces'']]
Both Charlie and Rocky use use a similar catch phrase "what da u hear what da u say" Both characters in each movie get out of prison in the beginning of the films, and both are betrayed by their former crime partner who tries to kill Charlie/Rocky to keep all of the casino they built together.
* Charle was even born about the time Rocky would have died!

[[WMG: The couple that adopted Anne-Marie are really...]]
[[http://en.wikipedia.org/wiki/J._R._%22Bob%22_Dobbs J.R. "Bob" and Connie Dobb]]. Because, come on, the resemblance is just too uncanny!

[[WMG: The whole movie was a hallucination of Anne-Marie's.]]
She was a half-starved orphan living in a garbage dump full of dogs, and out of loneliness personified the animals herself.

[[WMG: The Heavenly Whippet really ''did'' know everything that would happen.]]
''All'' dogs go to heaven, right? Even complete bastards like Carface (and rather more loveable bastards like Charlie). Even if they have done nothing to earn it. And the Whippet claimed that she knows everything that's going to happen, but Charlie manages to "surprise" her nonetheless. He returns to earth and manages to earn his redemption in the process. At the end Carface also plans to escape, and Charlie is convinced that "he'll be back". The whole plot actually makes a lot more sense if you assume heaven is running a BatmanGambit with these "bad dogs", letting them think they tricked their way back to life when its actually all part of the plan for them to redeem themselves. All dogs ''do'' go to heaven, but only because the bad ones all try the same thing Charlie and Carface did, with similar results.
** She just became a [[MagnificentBastard Magnificent Bitch]] (in [[JustForPun more way than one]]).

[[WMG: Charlie never went back to Earth.]]
When a dog winds up their watch or clock, they are sent to purgatory, set out to look like the place they came from, where a series of challenges and tests are set up to determine whether dogs like Charlie or Carface deserve a place in heaven, or if they should be sent to hell.

[[WMG: Red was the monstrous demon creature from the first film.]]
They've gotta be the same character...they've even got the same chin!

[[WMG: King Gator is a descendent of [[Disney/ThePrincessAndTheFrog Louis]].]]
Ever since Louis made it as a successful trumpet player, he managed to land a lovely lady gator wife ([[ChickMagnet or several]]) and started a line of musically-inclined alligators in the New Orleans area over the next few decades. While King Gator hasn't exactly sought a musical career, he still displays a love for song and dance and is quick to befriend anyone else with an affinity for music.
* But don't the films take place around the same time?
** Well, maybe they're brothers or cousins or something.

[[WMG: Charlie is a [[OurLichesAreDifferent lich]].]]
His watch was his phylactery (SoulJar in Tropese).

[[WMG: David's step-mother is Anne-Marie or a [[KidFromTheFuture descendant of hers]].]]
It may be possible, both have dark hair and blue eyes, it could very well be possible that David's step-mother could somehow be Anne-Marie living in a different life after the death of Itchy, he could have died while with Harold and Kate since Anne-Marie is an adult now. Also, we never see how David's parents react with Charlie and Sasha, but when he asks them if they would like a pet or two, they seem to accept as David gives them food bowls.

[[WMG: The backstory given in "When Harry met Silly" is a lighter and softer version of how Charlie and Itchy actually met.]]
Charlie didn't want to freak out the kids with details of gangsters, booze and graphic death. In addition, Annabelle would have been on his tail if he told [[DarkerandEdgier the real version]]. So he fluffed it up, crafting a well-rehearsed fable that hid certain details under a lightened curtain.

[[WMG: The reason Killer was absent in the second movie but is present in the TV Series and Christmas movie was because he possibly time-traveled between the first and second movie.]]
It might also explain the ray gun he fetched for Carface.

[[WMG:Belladonna, Red and the Hell Hound are all one horrible shape-shifting entity of evil a'la ''Literature/{{It}}''.]]