After being nominated for Grammy awards in four different categories for the album Nick of Time, Raitt went for a creative retreat in Northern California to begin work on Luck of the Draw. "I did it on purpose to see if I could come up with anything," Raitt said in 1991. "In case I won, I wanted to make sure that I had done some writing and didn't feel that Nick of Time was a fluke. I didn't want to win just 'cause I quit drinking and spent twenty years not making any money, you know? There wasn't enough. So I basically forced myself to go to songwriting boot camp. There were three of four days when it didn't happen — but because I didn't have alcohol or unhappiness or anything to get in the way, it started to open up and I started three of the four songs of mine that are on this album. And then it didn't matter if I won or not, because I had proved to myself that it was okay."
The album surpassed Nick Of Time's commercial success, having sold seven million copies in the United States alone by 2010, and was supported by a 180-date tour from 1991-1993. It replicated much of her U.S. success overseas as well, selling two million in France and Italy. It remains Raitt's biggest-selling recording to date.
According to the liner notes, Raitt dedicated this album to late blues guitarist Stevie Ray Vaughan.