Alan Jackson suffered one bad setback that changed his career

Apr 18, 2026

Alan Jackson was one of the biggest country artists of the 1990s. 

Success didn’t come easy for the Georgia native. 

And Alan Jackson suffered one bad setback that changed his career. 

Alan Jackson’s first single failed to gain traction with fans and the charts 

Country music legend Alan Jackson topped the charts in the 1990s on his way to becoming one of Nashville’s biggest stars. 

His first album, Here In The Real World, was released on February 27, 1990. 

The first single off the album, “Blue Blooded Woman,” failed to make the country top 40 charts when it was released ahead of the album in 1989 to generate interest in Jackson’s upcoming release. 

Every country artist wants to start their career off with a hit single. 

Jackson got a taste of defeat before his career began to take off. 

The second single from his debut album changed Jackson’s life and his career. 

“Here in the Real World” reached number three on the Billboard Hot Country Singles and was widely played on the radio. 

That song became the first successful single of Jackson’s storied career. 

Here In The Real World produced hits like “Chasin’ That Neon Rainbow,” “Wanted,” and the first number-one song of his career, “I’d Love You All Over Again.”

Jackson was worried after “Blue Blooded Woman” failed to become a hit. 

He was hoping that the single “Here In The Real World” would strike a chord with fans. 

“I was just writing songs, and I mean, ‘Real World’ was really kind of…not necessarily something out of my life or anything; it was just a story song about, you know, a love song, really,” Jackson recalled. 

“Wrote that with Mark Irwin, and turned out to be the first hit and the second single. The first one died, so that was my big hit that came after and saved me,” Jackson added. 

Alan Jackson was worried about his career after his first single failed to take off 

Jackson released his first album when his wife was pregnant with their first daughter. 

“Denise was pregnant with our daughter, was kind of scary,” Jackson explained. “You know, you never know, get one or two singles and then the label drops you, you know? So I didn’t know what was going to happen, but “Here In The Real World” kind of got it all going.”

The fourth single on the album was about Jackson chasing his country music dream in Nashville. 

“Then ‘Neon Rainbow’ that was just Jim McBride and I wrote that. We were just talking about where I’d come from and, you know, coming to Nashville and trying to get something going in the music business. Chasing that dream that so many people do,” Jackson stated. 

Jackson’s debut album became a big hit and was eventually certified as double platinum in 1994 after it sold more than two million copies. 

He followed that up with his sophomore album, Don’t Rock the Jukebox, in 1991 which cemented him as a country music star with number-one hits “Someday,” “Dallas,” and “Love’s Got a Hold on You.”

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