Open iTunes. Go to your library. Answer, no matter how embarrassing it is.

Sort by Song -
First Song: (I Just) Died In Your Arms - Cutting Crew
Last Song: Yuko & Hiro - Blur

Sort by Time -
Shortest Song: Horn Intro - Modest Mouse
Longest Song: Eskimo - Damien Rice

Sort by Artist -
First Artist: The 1910 Fruitgum Co.
Last Artist: The Zutons

Sort by Album -
First Album: (What's the story) Morning Glory - Oasis
Last Album: You Could Have It So Much Better - Franz Ferdinand

Search the Keyword - song title only - and see how many songs appear:

"Sex": 2
"Death": 3
"Love": 120
"You": 236
"Me": 260
"Drug": 2
"Hate": 5

Shuffle your library and list the first five songs. No padding your playlist you hipster, you. Be honest!! or I'll kill you.

1. Song For Kelly Huckaby - Death Cab for Cutie
2. Parachutes - Coldplay
3. Hui Dao Guo Qu - Jay Chou
4. Smoke Gets In Your Eyes - The Platters
5. Grace Is Gone - Dave Matthews Band

Total music: 2100 songs, 5.6 days, 8.79GB

That was fun!