Songfacts®:

• "Milkman" was borne from a song idea of Angaleena Presley's in which she thought about how her mother married young and was unable to identify with her daughter sowing her wild oats. She explained in a video interview:
  
  "My mum got married when she was 16 and my dad was 18 and they're still together. When I went off to college and started doing wild things, my mum had a really hard time with it because I don't think that she ever got to happen. She went to college but she had three kids and she was going to college so she didn't get to party that much so when I started partying she got a little judgey at times. I always wondered what our relationship would have been like if she had gotten to experience things those things. So that was where the song came from."
  
  Presley brought the lyric to the table during a Pistol Annies writing session and the other two girls "thought about their mums and they added stuff they could relate to."
• The song title comes from the idea that if Presley's mom had fallen in love with the milkman, she may have let her hair down a bit more and understood her daughter's desire to party. However, "mama never did love nothin' but daddy and me."
• The Annies knew they wanted some sort of harmony on the song but were undecided about which of them should sing what. Producer Frank Liddell resolved the issues by getting each of the three girls to record their parts without hearing what the others were doing. He then put the three vocal parts together.
  
  "It was like three different puzzle pieces coming together, but still very different," Ashley Monroe told The Boot. "I get deep chills every time I hear that part... one of my favorite moments on the record is when that happened."