As I was listening to "Holland, 1945" by Neutral Milk Hotel, I noticed that iTunes says I've listened to it 127 times. Which is a lot. But it also way understates it, because it doesn't count the times I've listened to it on CD (many), iPod (a good number), or on my computer before I got the version of iTunes that keeps these stats.
The ten songs I've listened to most often in iTunes are:
134 times: Animal Collective - Grass [YouTube]
127 times: Neutral Milk Hotel - Holland, 1945 [mp3]
107 times: Broken Social Scene - Anthems for a Seventeen-Year-Old Girl [YouTube]
104 times: Modest Mouse - Gravity Rides Everything [mp3]
104 times: Wolf Parade - Shine a Light [mp3]
96 times: Calexico - Service and Repair
96 times: Dismemberment Plan - The City
96 times: Modest Mouse - White Lies, Yellow Teeth
96 times: Radiohead - Karma Police [YouTube]
96 times: The Thermals - No Culture Icons [YouTube]
The median number of times I've listened to a song in my iTunes collection (4631 tracks) is 18.