The 25 Best Songs About Underwear

You've made it this far?! We’re going to take a mellow turn now – like a set break – but keep trucking and you’ll get to meet our surprise guest! 
From: The Underwear Expert

#19

Sleepwalking

Lyle Lovett

The Lyric

The police man spied me in traffic there, in my t-shirt and my underwear

he said son son it sure don’t look good

No, Lyle, no that doesn’t look good. Sure this is blues but is it autobiographical? Did it have anything to do with maybe a certain “pretty woman” and you? And what kind of t-shirt? What underwear? Details, man! Of course we won’t tell a soul.