On April 1, 1995, Trisha Yearwood’s “Thinkin’ About You” hit No. 1 on Billboard’s Hot Country Songs chart, beginning a two-week reign. It became the third of her five career leaders, among 19 top 10s.

No one can tell a story in song quite like Trisha Yearwood. Yearwood’s eponymous album came out in 1991. In the years since then, Yearwood’s reign as one of country music’s best storytellers continues ...