High Fidelity is another one that didn't immediately make an impact on me. As a 17-year-old, I walked away from the theater loving Jack Black's hilariously over-the-top know it all Barry, but not really connecting with John Cusack's self-loathing (yet occasionally arrogant) Rob, and his travails through the top 5 loves of his life, and why they didn't work out. A few years later, I watched the movie again and found it deeply affected me on an emotional level, now that I had some life experience with what Rob was talking about, and a deeper love of the pop-culture that Rob also cherishes. Now, as a 26-year-old with even more experiences, I find more than ever that I connect not just with Rob, but with Barry, Dick, Liz, and Laura. All the characters are amazingly well drawn (much of which comes from Nick Hornby's brilliant novel) and brilliantly played by the actors, with even Jack Black seeming like a real character, and not just Jack Black.
Sometimes a movie feels so personal to me that I fear showing it to other people, afraid that their opinion (whether positive, negative, or indifferent) will color mine in some way and my love of it will be somehow tainted. This is a movie like that. I occasionally hesitate in recommending such a deeply personal favorite, especially one that I don't think will connect with someone as fully as it does with me, immediately at least. Some people aren't willing to revisit movies that they didn't love the first time around. But I do have such a deep love and connection with it that I can't help but put it on this list and want to recommend it to anyone with an open mind.