The 25 Best Songs About Underwear

#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.

#18. Underwear, Loudon Wainwright III

The Lyric: You know when I know just how much I care / when I’m carefully folding your clean underwear.

Oh Loudon, you sad, sardonic, sad-sack of a sappy man. We hope you do find peace folding the laundry one day.

#17. The Stars of Track and Field, Belle and Sebastian

The Lyric: You only did it so you could wear / terry underwear

They’re not singing about a guy named Terry Underwear (though that’s a great name, we have to admit). It’s short for terry-cloth underwear. Which sounds … not so comfortable actually.

#16. There it is, Barry White

The Lyric: Let me undress you / from your clothes / to your underwear

Umm, Barry, we’re not trying to be rude or overstep our bounds or anything — I mean you are the reason like 80% of the children born in the western world are here — but, see, underwear are clothes. So we’re just — not sure how you undress us from our clothes to our underwear. It’s no big deal. Whatever.

Woof — that was serious and kinda sad. We could use a laugh right about now. Good thing when it comes to Underwear in songs you can bet a few of them will be comical.  15 more ’til the secret surprise guest arrives!

#15.  Inner City Pressure, Flight of the Conchords

The Lyric: You know you’re not in high finance / considering second hand underpants

Brit and Germaine give us a reason to get up in the morning. It’s called new wave synth send ups. Wow. Who does that?!

#14. The Underwear Song, Rodney Carrington

The Lyric: I found an old pair of underwear / hanging on a clothesline

We had planned to find a country song and use it to make fun of country, but wouldn’t you dog-gone know it, country beat us to the punch by making fun of itself. Touché country music, touché.

#13. The Willbury Twist, The Traveling Willbury’s

The Lyric: You put your hand on your head / You put your foot in the air / then hop around the room / in your underwear

We don’t know whether we should applaud Tom Petty, Bob Dylan, Jeff Lynne, and George Harrison or be really, really, awkwardly embarrassed for them. We’ll just watch John Candy in boxer shorts and not think about it.

#12. Homo Christmas, Pansy Division

The Lyric: You’ll probably get sweaters, underwear and socks

The next line — and pretty  much the entire song — says more than we ever could.

#11. L U V, John Mellancamp

The Lyric: Lying cheating everywhere / sexy boys in their underwear

Mr. Cougar Mellancamp are you saying that lying and cheating is the equivalent of sexy boys in their underwear. We disagree. Maybe it’s time you sang about jack and guy-anne, if you catch our drift. We said, good day, SIR!

AND NOW, THE FINAL TEN!! ARE YOU READY CLEVELAND?!  Just kidding. We just always wanted to say that.


4 thoughts on “The 25 Best Songs About Underwear

  1. Ron says:

    How did you miss the greatest underwear song of all time !???

    Let me be your underwear – Club 69

    Check it out on YouTube.

  2. Joshua Acosta says:

    Underwear by Royal republic. Literally just about a girl’s boss being able to see her underwear when he is laying on the floor.