Country music’s signature storytelling has captivated audiences for decades.

Music in the genre has a way of uniquely tugging at listeners’ heartstrings with deeply vulnerable stories of love and loss, hurt and heartache, and more. Legendary singer-songwriters like Patsy Cline, Alan Jackson, Charley Pride, Brooks & Dunn, Merle Haggard, Johnny Cash, Dolly Parton, Loretta Lynn and many others have paved the way for some of today’s powerhouse songwriters, including Luke Combs, Carly Pearce, Lainey Wilson, Chris Stapleton and Jelly Roll, to name a few.

Some artists have released music that connected with listeners so profoundly that those songs have stood out as some of the saddest of all time (iHeartRadio’s Bobby Bones even compiled a playlist of sad songs draft picks). In 2019, Rolling Stone revamped a ranking that originally published in 2014, listing the 40 saddest country songs of all time. Find the full list here, and see the five saddest country songs of all time below.

5. John Michael Montgomery, “The Little Girl,” released in 2000