Written by Naomi Judd and Mike Reid, "My Strongest Weakness" was released in December 1992 as the fourth single from Wynonna’s self-titled debut album. The song rose to number 4 on the Billboard Hot Country Singles & Tracks chart, quickly becoming one of her most powerful ballads.
Naomi said she got the inspiration for the lyrics while "sitting in a ditch behind a Holiday Inn in Rooster Poop, Texas."
Wynonna introduced the song saying: “It’s a deep one. If you’ve ever been bitter, party of one, your table is ready... my mama wrote it and I sing it from my toenails, because I lived this song.”
This typed lyric sheet preserves Naomi’s and Mike Reid's original draft.