Great essay. Maybe you should mention some of the historical landmarks near Penn in the paragraph that discusses location and culture. Mentioning the Penn traditions was also brilliant. Overall, great essay. I, too, am applying to Penn. I hope we both get in. =)
This is certainly not boring. It's actually very interesting, and the message is clear. By the way, you need a colon (not semicolon) after "how much we shared: love, appreciation..." Good job.
Good job. Yes, the topic is certainly unusual, but this is good because it will distinguish you from the other applicants. You did reflect on how this piece influences you, but, I do think you should work on this relection a bit more. For example, include why this piece is so important to you, and why this particular piece has such a strong influence, otherwise, you're just talking about a piece of music that you enjoy. Neverthless, you're certainly headed in the right direction, and the essay is very beautiful to read. So, good job, and good luck. =)
I actually thought the metaphorical use of the "road of life" was quite appealing. I hope you integrated your personallity and authenticity in your essay, but I'm sure the additional five paragraphs have accomplished that. If you made the essay unique, and really accentuated on how this road has changed you, then the essay is certainly not cliche. Good job, and good luck. I, too, am applying to the University of Chicago.