Alan Jackson’s Heartbreaking Song ‘Sissy’s Song’: The Story Behind The Classic Country Hit

by Matthew Wilson
Photo credit: John Shearer/Getty Images for Acme Feed & Seed

Alan Jackson’s had many hits over the years, but Sissy’s Song is Jackson at his most tender and mournful. The country singer tells of a woman who died too early in life and left her family behind. Now Jackson revealed the painful true story behind the song.

Speaking with The Boot, Jackson said he wrote it after a housekeeper who worked for him died. Leslie Fitzgerald, or Sissy as people called her, died in a motorcycle accident on May 20, 2007. Her death shocked Jackson because of the sudden loss. He didn’t expect someone so young to die.

“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,” Jackson said. “She had an accident on a motorcycle, she was 40-something. 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.”

Alan Jackson wrote ‘Sissy’s Song’ for Leslie Fitzgerald’s funeral.

Jackson said he wrote the song specifically for Fitzgerald’s funeral. But later, he decided to include the song in his album Good Time.

“It’s a real special song for me. I recorded it for the funeral, but [producer] Keith [Stegall] and I went into the studio one day and put the guitar and vocal down,” Jackson continued. “It’s just me and the guitar and the harmony parts. After some people heard it at the label, everybody wanted to put it on the album.”

Jackson released the song as the fourth single on the album in March 2009. The song went on to place No. 9 on Billboard’s country chart and No. 61 overall.

[H/T: The Boot]