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Sam's dad is in the mafia
And it manifests itself in the land of darkness as the bridge. The bridge is very mob-like with his greediness, aggressive nature and one of his click points he talks about having "friends" If we believe the common theory that the land of darkness is just Sam pretending this based on the events in his life, then this is likely his dad. It could also explain the vast number of characters as well.

Everyone in the land of darkness is dead
How they died is a clue as to why they are a certain object or say a certain line. For example:

The nice tree was a kind old lady who died of old age.

Otto was an eight year old child. One day, he went out for a boat ride in a wooden boat when it tipped over. Otto, unable to swim, died. That's why he thinks wood sinks.

King died in a coal mine explosion where he suffocated/starved to death. His "rust on the tracks" meant he was unable to get out.

Carrot was an activist who was assassinated.

Pencil was a child accidentally left behind in the park where he got hit by a car.

The toaster died from an eating disorder. He used to play with his food and not eat it, that's why the cheese has to stay in the park.

The wishing well worked itself to death.

The grandfather clock died at the age of two many years ago from an unknown disease. It was likely before modern medicine. This explains why he has to enjoy "every minute."

The pieces of kitchen equipment were restaurant workers killed in a kitchen fire at lunchtime. This explains why it was always lunchtime.

The living room furniture: A family killed when someone broke in and killed them. They think Sam is the one who kills them.

Wink and Blink were a gay couple who got murdered. More specifically, Wink was murdered and Blink survived. That explains why Blink wants all of Wink's power. It's survivor's guilt.

The three trees guarding the garden: victims of a hate crime. The last thing they saw were trees, so now they think that all trees are good and everyone else is evil.

The chair: Murdered in her home. She was shot in the leg and bled out. It explains why she says phrases from the game Clue, and why it's her leg that breaks.

The bridge: Committed suicide by jumping off a bridge after suffering a major financial blow.

The instruments: Musicians who died in a car accident.1. The head was the driver and decapitated in the accident.2. The organ was in the passenger's seat. He kept telling the head to be careful, but he wasn't.3. The trombone survived the accident, but suffered a brain injury making him unable to speak. This is why he does not speak. He died years later of natural causes.

The events of Pajama Sam 2 caused the climax of Ouendan 2
When Pajama Sam had accidentally pressed the big red button, it had caused parts of the World Wide Weather to scramble. One of the machines affected was the sun machine, which didn't get its fuel due to the lack of Wing Nut. In result the sun was on the verge of dying. As Pajama Sam was getting Wing Nut back to its place, the both rival Ouendan realized the need to teamwork. The teams cheered and so did the Earth, giving the Sun enough energy to survive longer. Eventually Wing Nut is restored to his place, and the sun was restored to full health.

Pajama Sam's house is a TARDIS
If you think about it, he goes into his closet and he finds the Land of Darkness and he goes into the pantry and finds himself in Level Ate.

Paper knows that the plunger is his, and he is a Jedi
When Sam grabs the plunger from the ski route, Paper knows that it is his plunger but he sensed by using the Force, that the Sam needed it to save the world.

Pajama Sam owns at least two editions of Pajama Man issue #1, each with a different cover
Each cover corresponds to one of the stories in the issue. The edition with Dr. Grime on the cover is by far the rarer of the two.

Pajama Sam's future self wrote/will write the Pajama Man series.

Sam's house is an interdimensional hub— and his mom knows.
Since we never actually see Sam's mother, I'm gonna peg her as non-human: She has blue skin, like her son, so we've already got a bit of evidence in that direction. This theory states that not only is she a non-human entity, she has the ability to create and manipulate portals to other universes. She's kind of an interdimensional explorer, who gave up her day job to settle down and raise a kid in a nice suburban community.

However, she still retains the power— and she uses her connections with dimensional deities to help her out with parenting. Kid's freaking out over sleeping in the dark? Well, hey, you slept in that guy's guest room for a month in college. Kid won't eat his veggies? Seeing the effects of political imbalance amongst the food groups will teach him to have a balanced diet! Thunder and Lightning? Oh, they're just the nicest couple! Of course they'll put him up in the weather machine for a night— hopefully, he doesn't break anything.

Anyway. This would explain why the characters in the "pretend" worlds make pop culture references and jokes that go over Sam's head, and why everything always works out fine in the end. And as a bonus? That carrot that's in every game is an interdimensional traveler as well. And, though it's going out on quite a limb, he's Sam's biological father. It was a fling back when his mom was younger, okay? He's clearly a child of the 60s, so it sounds about right, age-wise. She'd been meaning to have a little explorer of her own, anyway.Sam's mom sends Sam off on interdimensional travels to raise him correctly, and Sam's dad watches over him on these adventures.

Sam is friends/neighbors with Ned Needlemeyer.
Sam's adventures all deal with moral issues in his life, with a hyper-active imagination that makes them appear to inhabit entire worlds. Furthermore, manipulating these worlds allows Sam to understand and cope with said issues. Ned Needlemeyer goes through the same process with his nightmares, albeit in a far darker, more abstract way.It wouldn't be surprising if they went to school together or something.

Pajama Sam is an adult on some sort of drug.
Most likely a hallucinogen. Each episode is him hallucinating at a different setting.

No Need to Hide When It's Dark Outside takes place at his house and surroundings, Thunder and Lightening is his hometown, You Are What You Eat is at the grocery store.

If by some miracle Humongous Entertainment starts making new games, the next Pajama Sam game will be called Pajama Sam 4.
  • Considering how... Infamous Life Is Rough When You Lose Your Stuff! is, along with the fact that it is technically an unnumbered installment, I can see them doing what Crash 4 did.
    • Pajama Sam 4: It's About Time For Fun When In Competition.

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