I can see your point in that the kolmogorov complexity of two lines in a song isn't much larger than one line. Similarly, 30 digits of pi and 300 digits of pi have very little difference in kolmogorov complexity.
What I don't know is if state-of-the-art password guessers are great at recognizing larger patterns in the entire canon of human knowledge. I.e. is there a "common phrases" attack that's analogous to a "dictionary attack"?
Google released the world's largest corpus and did us a favor by analyzing it for n-grams. For example, they found that the phrase "serve as the initial" was over a 100 times more common than the phrase "serve as the insurance". [1] For $150 you can buy the 24GB data set yourself, so it's a fair assumption that makers of password crackers could reliably guess common phrases first. [2]
That may be true, but we still end up better off. The compute time for the password cracker has gone up quite a bit, making it a more expensive endeavor (they've got to build dictionaries for both WKP's and passwords with fuzzing). It doesn't solve the problem, but it's a start in the right direction (away from fuzzing of dictionary words, which is clearly bad for human memory, and good for password crackers efficiency).
However, when using randomly chosen dictionary words to build phrases (not well known), the entropy shoots well above the level of being reasonable to crack in a lifetime.
Given that the knowledge about correct parts of a password based on known sources (pi, peace and war, song lyrics etc) drastically reduces the amount of possible solutions. But how would an attacker figure out the first part of such a password? What comes to mind are timing attacks http://en.wikipedia.org/wiki/Timing_attack
What other possibilities did I miss?
EDIT: I get that having a long streak of my pass in a dictionary would reduce overall security but it's still unclear how a partial match in the dictionary would be detected.
What I don't know is if state-of-the-art password guessers are great at recognizing larger patterns in the entire canon of human knowledge. I.e. is there a "common phrases" attack that's analogous to a "dictionary attack"?