I'm kind of OCD when it comes to my iPod and the things played on my iPod. As in, I'm really picky about making sure that things are played to their completion, so that the "Play Count" number and time get recorded. If you stop it with even one second left, the Play Count doesn't tick over, you see. So, I love to see how many times I play stuff.
In my music, the highest playcounts - over 60, each - come from the Ron Meixall vocal warm-up CD that the Big Apple Chorus used to use. I alternated between that one and one by Roland Wyatt, and my top 15 spots are held by that. After that? "Goodnight Moon," the video that was put on my iPod just before The Boy's last hospital stay, with 44 plays - tied with the learning track for "Hey Good Lookin'" and Vocal Spectrum's "Cruella De Ville."
The highest non-barbershop, non-learning, non-warm-up tracks are Max Q's album, "For the Children," which is in the high 20's. The highest pop music play counts are the Weird Al Yankovic "White and Nerdy" video (20) and Metallica's "Enter Sandman" (19). Just in case you're interested.