The Devastating Story Behind Alan Jackson’s ‘Sissy’s Song’ Is Heartbreaking

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Country music legend Alan Jackson‘s heartbreaking hit “Sissy’s Song” brought listeners to tears upon its release in 2009. However, with every sad song typically comes a tragic story or various forms of tearjerking experiences. In the case of the “Livin’ On Love” singer, this song hit close to him, literally. Jackson told The Boot,

“I wrote it for a girl that worked for us who died. She was a lady that looked after the whole house. Leslie Fitzgerald was her real name, but we called her Sissy. She had an accident on a motorcycle; she was 40-something [when she died on May 20, 2007]. She was just somebody who was in our house every day … then, all of a sudden, [she was] gone. When people get old, you expect them to die, but it’s different when they are young and it’s tragic like that.”

Jackson went on to explain how he had recorded the song for the woman’s funeral. It wasn’t until later on that the song was praised by various listeners that Jackson was encouraged to add this ballad to his 2009 Good Time album.

The song speaks of unbearable heartbreak, confusion and the sad truth that death can often be sudden and without reason. Listen to the lyrics below to capture the incredible gift that Jackson gave this clearly unforgettable woman.