I was looking at some numbers yesterday, and found out that "Dashboard" by Modest Mouse is the first song to reach 100 plays on my iPod. I guess it's not surprising since I was totally obsessed with this album for nearly all of 2007.
I'm sure there have been other songs I've heard more than 100 times. A few that come to mind include "Vogue" by Madonna and Hole's "Celebrity Skin." It's just that this is the first one since I've had my iPod. A contributing factor was getting my iPod hooked up to my truck--probably the best money I've ever spent.
There are a few other artists who have songs nearing the "100 Plays" achievement. Among them, the Yeah Yeah Yeahs, We Are Scientists, The Distillers, Peaches, Luscious Jackson, the Arcade Fire, and of course, Sleater-Kinney.
Occasionally, I'll listen to an album non-stop and get tired of it after a few weeks; but some albums never get old. If anyone has the formula for a timeless record, let me know.