Songfacts®:

• Toby Keith penned this light-hearted rocker about two buddies with the Nashville songwriter Rivers Rutherford. He explained that the song's title was something his father used to say. "I always thought it was funny," he said. "See a pretty girl and go, 'Look out, boys. That's the size I wear right there.' It's like when me and Scotty (Emerick) wrote 'As Good As I Once Was.' That's something my dad used to say, too. He also used to say, 'I don't know what I'd do if your mama ever left me … guess I'd just go with her.' Me, Scotty and Dean Dillon wrote that one ("Go With Her").
  
  "Stuff like that is very intriguing to me and I had it laying around," he continued. "Rivers took off on it and we decided it was about a couple buddies drinking. I had the 'Five-foot-two, 95 pounds. Round in the places she's supposed to be round' and Rivers just flipped over it when I told him the idea. There was another little piece that didn't work, but Rivers fixed the chorus and then we wrote the verses. It's just comical."