No song quite exemplifies that connection for me than "If You Were Here" by the Thompson Twins. For those not in the know, this is the song that closes out "Sixteen Candles." The mood of the song is a perfect ending to the movie, masterfully setting John Hughes fans up for even more impactful combinations of music and scene in his later movies (think "This Woman's Work" in "She's Having a Baby" or "Oh Yeah" at the end of "Ferris Bueller's Day Off").
The funny thing is, I have rarely listened to "If You Were Here" outside of the movie. I couldn't sing you every lyric, and honestly, it's not the best Thompson Twins song out there (I'm going with "Love on Your Side"). It just sounds amazing in those closing credits, to the point that I don't turn off the movie). I hear it, and it feels so '80s, and new wave, and alternative, and sweet, and electronic, and mellow, and North Shore, and teen ... that I just want to close my eyes and remember visiting my godparents' house in Glenview in 1985. Or running on the North Shore trail with my cross country team in high school. Or dreaming of a girl I liked 30 years ago who lived in Deerfield who I never had a chance with. Or driving with my friends up the Edens Expressway. Or working at my uncle's school in the summer of 1989, taking my bike every day through the green streets of Northfield.
Granted, this wasn't quite my world because I lived in the city and only went to school in Niles. But for a certain subset of teens, it felt like John Hughes was making movies for us and just us. "If You Were Here" captures so much of that. It accompanied the sweet conclusion to the movie that was more in line to what most teens felt rather than the dumb sex comedies of the 1980s. And it just sounded great -- on so many levels.