"When You Leave That Way You Can Never Go Back" is a song written by Steve Clark and Johnny MacRae. The song—a bittersweet reflection of a condemned inmate's life, looking back at all the bridges he burned and wished could be repaired—was recorded by several country music artists, including Sam Neely, Bill Anderson and the band Confederate Railroad.

"When You Leave That Way ...", told in first-person narrative, begins with the man remembering some things about his childhood with fondness: his mother, waking to the rooster's crow and listening to Arthur Godfrey. However, his relationship with his father is very strained; after the two get into a fight one morning, the boy runs away and never returns home, beginning his troublesome life as a drifter.

Later, the man tries to settle down and eventually gets engaged to a young woman; however, on his wedding day, he leaves her standing at the altar. Later, he begins a relationship with a woman who is married; when her husband walks in on them, he shoots and kills him, eventually leading to his death sentence. (Just before the revelation of the latter of these events, within the bridge of the song, he mournfully tells how he wishes he could repair his broken relationships with his parents and hold his young son.)

He burns his final bridge when a clergyman comes into his jail cell to administer the last rites, shortly before he is to be put to death; however, the man tells him to go away.

Sam Neely recorded the first charting version of "When You Leave That Way ..." in 1983 for the MCA Records label. His version peaked at No. 77 on the Hot Country Singles chart that year.

Bill Anderson later recorded the song for his 1985 album Yesterday, Today, and Tomorrow.^[2] His version went to number 75 on the country music charts.

In 1992, Confederate Railroad recorded the song for its debut album, also titled Confederate Railroad. The song was released in 1993 as the fourth single from the album, reaching a peak of number 14 on the country music charts.^[3] It was also the b-side to the album's fifth single, "Trashy Women."^[3]

An uncredited review in The Miami Herald referred to the song positively, calling it a "soft, poignant song about burning bridges that can't be rebuilt."^[4]

The video was directed by Martin Kahan and it starts by seeing a man in coveralls attempt to chase a small child down a gravel road, then upon the sound of the prison cell door, the song begins with the man's flashback to the altercation with his father that got him to leave home, his meeting with the girl he stood up at the altar to him in prison, with his father reading about the execution in the local newspaper. The video concludes with the man in the coveralls (revealed to be his soul) returning to the farmhouse and seeing his son and father mourning. The video also cuts to the band performing the song in a room.