In "Johnny 99" Springsteen sings about an auto worker who gets laid off in Mahwah, New Jersey and shoots and kills a night clerk while drunk and distraught. As a result, he is apprehended and is sentenced to 99 years in prison, but requests to be executed instead. On the song, Springsteen is accompanied only by his acoustic guitar. Despite the bleakness of the song's themes - including unemployment, poverty, robbery, murder and possibly execution - the tune is ironically jaunty, with a shuffling rockabilly beat.
Like several other songs on the Nebraska album, "Johnny 99" is a song about complete despair. It has direct links with certain songs on Nebraska: the protagonist in "Johnny 99" notes that he has "debts no honest man could pay," repeating a line used by the protagonist in "Atlantic City", and, like the title song, "Johnny 99" is about a murderer — though rather than being a psychopath like the protagonist in the title song, "Johnny 99" is motivated by his economic circumstances.
Like the rest of the Nebraska album, "Johnny 99" was recorded in January 1982 in a no-frills studio set up in Springsteen's home in Colts Neck, New Jersey. Most likely it was recorded on January 3, 1982, when most of the album tracks were recorded.
The background of the song is based on a real life incident, the closing in 1980 of a Ford Motor Company plant in Mahwah, which had been open since 1955. The song also has antecedents in two folk songs that appeared on the box set Anthology of American Folk Music: Julius Daniels' "99 Year Blues" and Carter Family's "John Hardy Was a Desperate Little Man".
Despite its bleak themes, it has been a reasonably popular song in concert, with 379 live performances through May 2014. A live version was released on the album Live/1975–85. During a September 22, 1984 Born in the U.S.A. Tour concert in Pittsburgh, Springsteen used the introduction to "Johnny 99", to respond to President Reagan referencing the message of hope in Bruce Springsteen's songs, stating "The President was mentioning my name the other day, and I kinda got to wondering what his favorite album musta been. I don't think it was the Nebraska album. I don't think he's been listening to this one."
Other artists have recorded "Johnny 99". Most famously, Johnny Cash recorded this song along with another Nebraska song, "Highway Patrolman" for an album that Cash entitled Johnny 99.The song has also been recorded for Bruce Springsteen covers albums by John Hiatt and Los Lobos. Punk rock band The Loved Ones covered the song on their EP, Distractions. Mark Erelliand Jeffrey Foucault also covered the song for Seven Curses, an album of murder ballads. The band Shovels and Rope covered the song as well and perform it occasionally live.
In praising the album Nebraska, "Johnny 99" is one of the songs that was singled out by Mikal Gilmore of the Los Angeles Herald Examiner. In discussing Springsteen's growth as a writer, he stated that "When Springsteen tells Charlie Starkweather and Johnny 99's tales, he neither seeks their redemption nor asks for our judgment. He tells the stories about as simply and as well as they deserve to be told - or about as unsparingly as we deserve to hear them - and he lets us feel for them what we can, or find in them what we can of ourselves."