You have to tell the truth no matter how embarrassing. You may omit Podcasts and AudioBooks if you’d like. If you use symbols to force sort stuff where it doesn’t normally appear (such as tildes) you can go to the first naturally sorted item.
What are you using to answer? iTunes 10 for Mac
How many songs? 5315
Sort by artist
First artist: A-Trak
Last artist: 33Miles
Sort by song title
First Song: AA 24/7 (Dance Mix)
Last Song: 2000 Miles (Coldplay)
Sort by time
Shortest Song: Hope the Rock Show Goes Good (FM Static)
Longest Song: Autumn Interlude (Amethystium)
Sort by album
First Album: AA 24/7
Last Album: 2010 SideOneDummy Records Summer Sampler
Sort by “Last Played”
What was the most recent song played: Highway 20 Ride (Zac Brown Band)
What was the least recent song played/when: Operation Everything (Seth Frentsos)
First song that comes up on Shuffle*: Mr. Brightside (The Killers)
(If you don’t have Shuffle on your device, what would you like to come up next time you press PLAY?)
Search for these terms
How many songs come up?
Try it and see what you get and let me know in the comments.