Although many specific/linear interpretations of this song will work, I get much more out of the song when I think of it metaphorically and relate it to the human psyche. This is what the video for the song is trying to bring out imo.

In the video for Shock The Monkey, we see a business man in a suit trapped in a very dark, uncomfortable room with lights flashing in from the outside. This room represents the physical/material world. The lights are very invasive, which indicates feelings of paranoia and fear. We also see a few quick flashes of a statue of a human head with stones underneath the skin. Note that with each passing flash of the statue, the head becomes gradually more hollow and mechanical inside. This is symbolizing the split between modern man and his inner psyche (i.e. his connection to the spiritual realm is frozen or cut off… in other words, it has turned to stone and his inner spirit is eroding).

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The man sits down at a desk, opens his briefcase, and takes out some paper with the words “shock the monkey” written on it in different languages. There’s also a projector playing a movie showing monkeys. The man becomes increasingly frustrated and scared, as he can’t seem to keep his desk from violently shaking and disrupting his work. This represents his inability to control his repressed inner demons which are now bubbling to the surface in a disruptive way.

His specific “demons” are difficult to identify from the video alone, but the lyrics of the song (and other comments made by Peter Gabriel) definitely indicate that these are feelings of jealousy in relation to a woman (that’s why he specifically says “darling” in a few lines). But again, the main idea is that this man cannot control his fear because he keeps trying to repress it instead of dealing with it in a healthy manner. So we see the man become exhausted trying to push these feelings back down, as he slumps back into his chair.

The camera then fades over to the same man in a similarly-structured room. Only now, the man and the room look much different. He’s dressed in white, and his skin is also painted white. This represents the man as a spiritual being… a being of light and energy who is not living in constant fear because in the spiritual realm, nothing is repressed… so there’s nothing to really be afraid of (or to be jealous of, to be addicted to, to covet, etc.). You’ll notice that he’s sitting comfortably at his desk letting white chips fall from his hands. This shows that he is not afraid to “let the chips fall where they may”. He’s able to comfortably work around the things in his environment that he cannot control.

In this room, we also see that the lights are located on the inside this time, rotating around and making the room much brighter and more dynamic than the previous one (indicating that this spiritual being understands that his fears come from within himself and they are malleable, just like the physical world). He sits cross-legged on the floor in a meditative position, holding two red sticks that he apparently uses to create a spark. I’m not sure of the exact significance of the sticks, but I think they’re generally symbolic of the initial spark (or “shock”) that ignites man’s desire to reconnect with his spirit (or his unconscious, or whatever you wanna call it). This might also be referred to as “the process of individuation”, “alchemical transformation”, “rehabilitation”, etc. These are all essentially the same idea that this song is describing.

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Anyways, this “spark” ignites a circle of flames that surrounds the spiritual man sitting on the floor (showing that he is in perfect balance), while the paranoid material-man runs frantically through a forest (completely unbalanced, and victimized by his unconscious). As the spiritual man meditates in the fire ring, we see the paranoid material-man jump through the ring after being submerged in water. This shows us that the man is starting to become in-touch with his spiritual self. His unconscious spirit is shocking his conscious-self, which initially makes things even more uncomfortable for him in the physical realm (hence the line, “don’t like it, but I guess I’m learning”). That’s why it starts to rain in his dark room, and the ceiling starts to fall.

Then we see the spirit-man in the white room letting chips fall on the table again, while he laughs at a shadow of a monkey on the wall. He’s laughing because he is in touch with his shadow-self. His shadow doesn’t weigh him down, as opposed to the paranoid material-man whose monkey is much more than just a shadow on the wall. It comes in the form of midget people who literally hang on his back and arms, pulling him down and rendering him virtually immobile.

The spirit-man then flips one of the white chips as if it’s a coin-toss, and then we enter a new room with a “gabriel” sign on the door. This new room is the material-man’s imagined new office. This new room is much more spacious and comfortably lit from the inside. You can also notice the statues on his desk, which are the same statues that we got quick flashes of in the beginning of the video. These statues symbolize the death of his former paranoid, fearful self. The material-man appears much more relaxed as he flips a coin just as his spirit-self did.

Finally, we flash back to the paranoid version of the material-man who has his head down on his desk. This means that he’s been dreaming of the scene we just saw in his ideal, comfy office where he’s a much calmer version of himself. This tells us that he’s had a vision of a better life for himself because he’s becoming more in-touch with his whole psyche, not just his ego-self. That’s why when he wakes up from the dream, we see that his face is painted white just like the spirit-man. He has “shocked the monkey to life”, and is on his way to becoming a more enlightened human being who can live a richer, fuller life.