28 Years Ago Today, Alan Jackson Released the Frothy Love Song That Became His 16th No. 1 Hit

On this day (October 19) in 1998, Alan Jackson released “Right on the Money” as the second single from his seventh studio album High Mileage. Written by Phil Vassar and Charlie Black, the song spent one week at number one on the U.S. country songs chart in January 1999. It marked Jackson’s final chart-topper of the 1990s and the 16th overall of his career.

In January 1991, Alan Jackson reached the top of the U.S. country charts for the first time with “I’d Love You All Over Again”, the final single from his 1990 album Here in the Real World.

He would become quite familiar with that position, having since sent 25 more songs to the top of the charts. Even as more pop-oriented influences began to creep into country radio through the 1990s, Jackson held firm to his traditional stance.

Alan Jackson Dominated the ’90s Country Charts

A well-established genre mainstay by this point, Alan Jackson released his seventh studio album, High Mileage, in September 1998. The album rocketed to the top of the Billboard Top Country Albums chart. It even managed to crack the Top 5 of the Billboard 200, peaking at number four.

Impressively, all four singles reached the top 5 of the U.S. country songs chart. But only one—”Right on the Money”—claimed the number-one spot.

While Jackson has proven many times over that he knows his way around a tearjerker (“Remember When” and “Someday”, anyone?), this breezy tune is an unabashed declaration of love to a woman Jackson considers the perfect partner.

There’s absolutely no reason to doubt her / When she says I wouldn’t last ten minutes without her / She’s right on the money.

Notably, “Right on the Money” also marked Phil Vassar’s third number-one hit of 1998. He had already scored a pair of chart-toppers recorded by Jo Dee Messina — “Bye Bye” and “I’m Alright.”

Jackson had already reached number three on the U.S. country songs chart with the album’s lead single, “I’ll Go On Loving You”.

After topping the charts with “Right on the Money”, the follow-up singles — “Gone Crazy” and “Little Man” — peaked at numbers three and four, respectively.

[RELATED: Born 68 Years Ago Today in Georgia, the Country Music Hall of Famer Who Helped Revive the Genre With a String of 90s Classics]

After selling more than 75 million records across the globe, Alan Jackson officially retired from touring with a final concert at Nashville’s Nissan Stadium on June 27, 2026. He recently celebrated his 68th birthday on October 17.

Featured image by Getty Images/John Atashian