iTunes counts how many times you listen to songs. You can even sort your library that way. So I decided to see what my biggest songs were.
The only thing that throws off the count is that I don't think my old 3rd generation iPod (the white one with no clicking buttons on the front, circa 2003) does the counting, and it gets the most action because it's in my car. My newer iPod with video from 2005 does count I'm sure, and that one is mostly in my bedroom. That's maybe a playlist a night. Naturally the newer Apple TV and iTunes itself does count, as does the iPhone. The point is that there's a bias toward stuff in the last two years or so. So here's the count:
185 - Shine, Tracy Bonham (not surprisingly given it's my favorite song of all time)
171 - Up To The Roof, Blue Man Group (with Tracy)
163 - I Have to Save The World, Venus Hum
159 - Naked, Tracy Bonham
159 - Edge of the Ocean, Ivy
148 - Daylight Robbery, Imogen Heap
147 - Everything (Between Us), Liz Phair
139 - Chant Jam, Blue Man Group
137 - Silent Movie, Natasha Bedingfield
133 - I Feel Love, Blue Man Group and Venus Hum
129 - Have You Got It In You?, Imogen Heap
129 - Just a Ride, Jem
126 - Typical, Mute Math
123 - White Flag, Dido
122 - Time to Go, Cirque du Soleil: Delirium
119 - Sojourn, Natasha Bedingfield
118 - PVC IV, Blue Man Group
113 - Goodnight and Go, Imogen Heap
105 - See the Sun (live), Dido
105 - Headlock, Imogen Heap
I never look at my play counts. I may have to analyze my listening soon. I do listen to a lot of podcasts, so who knows how that impacts things.
Here's a question: What qualifies a play in iTunes? Is it a certain percentage of a track, or just reaching the end? For example: I am listening to "Wolf Like Me" by TV on the Radio. If I have one minute left and I go to the next track, is it still a play?
Answered! The track just needs to finish. If you want to cheat the play count, you just skip to the last few seconds of a track and let it play out.
(edits: 1) to add question, 2) to answer.)