She was singing hemorrhoid-medication jingles on national television in her 30s — then at age 45 became the first woman ever to win the CMA Song of the Year. K.T. Oslin shattered country music's age and gender rules with 80's Ladies, the song critics crowned the anthem of a generation.

Dropped by Elektra after a debut single that charted for "about 15 minutes," Oslin fought through depression and a return to hollow jingle work before betting everything on one final Nashville showcase in 1986. RCA's Joe Galante saw her theatrical delivery and lyrical maturity as assets, and the late-blooming songwriter rewrote what mainstream country let women sing about — divorce, aging, and messy adult life.

• Her failed first single, Clean Your Own Tables, charted for about 15 minutes by her own joke

• Signed her major label deal ...