First my daughter's iPod starting sounding strange. When she let me listen (took some negotiation), it seemed as if the sound had dropped either all, or a significant chunk of, the bass response. Singers no longer sounded autotuned (!). Wiggling the plug in the 1/8" connector sometimes helped, as did changing earbuds. Then tonight, on a flight home, I experienced the same problem with my own (otherwise perfectly reliable) earbuds on the aircraft entertainment system: very attenuated bass and midrange. Instant bad karaoke.
What could be going on with the connector? I could understand crackle and complete loss of signal, but this seems very frequency selective. If the input stage has a high-pass filter on it, wouldn't increasing impedence lower the cutoff frequency, not raise it?