The Story behind Waylon Jennings’ Oldie “Rainy Day Woman”

Written and recorded by American country musician Waylon Jennings, “Rainy Day Woman” utterly compares the ironic nature of life’s ups and downs to a woman. This track was the second single released in December 1974 to his album The Ramblin’ Man. It climbed the Billboard Hot Country Singles and Tracks chart at No. 2 and the Canadian RPM Country Tracks at No. 18.

Jennings’ gritty baritone was prominent in the song, which embodied the outlaw country culture. Stephen Thomas Erlewine of Allmusic pointed out that the tracks of The Ramblin’ Man “has a wilder sound and a greater diversity of songs that make it seem more unruly than its immediate predecessor and more blatantly outlaw.” This is a testament to the country singers’ significant force in the 70s to produce Waylon Jennings’ greatest hits that challenged traditional Nashville sound.

Fast forward to 1994, Mark Chesnutt covered the song and made a duet with Jennings for Chesnutt’s album What a Way to Live.

Meaning Behind the Song

Waylon Jennings’ “Rainy Day Woman” is one of those songs that you would find yourself unexpectedly jamming to. When life gets tough, he compares life to a woman who is only around “rainy days” but disappears during good times. One thing about that woman, though, is she has “been a friend” to the man.

Jennings’ adroit ability to add humor and excellent guitar work in the song cannot go unmentioned. The singer’s ragged and rough vocals perfectly sum up its old country vibes, which fit the narration of a complicated affair with a woman who cannot be easily satisfied: “That woman of mine, she ain’t happy; ‘Till she finds something wrong and someone to blame.” This seemingly propounds the idea of their love affair’s struggle to bloom.

The lyrics can have varied meanings but its relatability will remain. If you look at it more deeply, the song also suggests that what we take for granted is what we need all along.

Comfort yourself in Waylon Jennings’ vocal performance of the oldie but goodie song, “Rainy Day Woman.”