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“‘Til I Was Loved By You” was included on Wright’s debut studio album Woman in the Moon. Written by Jackson and Mark Irwin, the song reached No. 48 on the Country Airplay chart in 1994. Wright earned her first Country Airplay top 20 hit with “Shut Up and Drive” in 1997 and topped the chart in 1999 with “Single White Female.”

In 1996, Faith Hill released his Jackson-penned ballad, which became a top 10 Country Airplay hit. The song centers on a woman who spends years shaping her life around her husband’s preferences, only to realize she needs to live her own life.

In the early 1990s, Hill was opening shows for Jackson on tour, and asked if he would write a song for her album. In an interview with the Chicago Tribune in 1995, Jackson said he wrote the song because, “I’d felt some of that [female self-sacrifice] in my own life and witnessed it in other people’s. It’s a pretty standard kind of story, really.”

He also noted that Hill turned down his first attempt to write a song for her.

“I wrote this thing that was kind of country and was for a girl,” Jackson told the outlet at the time. “‘It’s Time You Learned About Goodbye’ is the name of it. Good song. I think somebody else might cut it. But she said, ‘That’s a little bit more country than what I’m doing’ or something like that. I said, ‘Well, I’ll just go write another one.’ So I thought I’d write something that wasn’t very country. That song (‘I Can’t Do That Anymore’), the melody and all, is not real traditional country stuff. So I wrote it, and she liked it. And I’m glad.”

In 1994, Clay Walker reached No. 1 on Billboard‘s Country Airplay chart with this uptempo, love-filled hit. Jackson wrote the song with Keith Stegall and Roger Murrah.

“The first time I’d ever heard that song, it was [Alan] singing it,” Walker told CMT, adding that his producer James Stroud told him Jackson was letting him have the song. Walker also noted that after the song went to No. 1, Jackson went to Walker’s hometown of Beaumont, Texas to do a concert: “He actually did that song, ‘If I Could Make a Living,’ and said, ‘Hey, here’s one recorded by one of y’all’s hometown boys and written by me.’ That was just one of the coolest things. I did get a note from Alan saying how proud he was that the song had gone No. 1. Just getting that note was pretty special.”

Jackson and Randy Travis co-wrote this 1991 release, which went on to become one of Travis’ signature hits. The song depicts someone who is growing disconnected from his lover’s preference for a “high society” lifestyle, preferring to associate with people who prefer a simpler style of living.

Jackson and Travis were touring together and decided to write some songs. In addition to “Better Class of Losers,” two other Travis-Jackson co-writes were included on Travis’s 1991 album High Lonesome: “Forever Together” and “I’d Surrender All.”

“It was close to time for Randy to record, so he got first choice on the songs we wrote,” Jackson told American Songwriter in 1992. “Maybe next time it’ll be the other way around.”

It was — Jackson later went on to release another Travis co-write, “She’s Got the Rhythm (and I Got the Blues),” which reached the No. 1 spot on the Country Airplay chart in December 1992.

This song, co-written by Travis and Jackson, was included on Travis’ album High Lonesome. The song reached No. 1 on Country Airplay.

Jackson and Travis had a run of success with their co-written songs, also earning hits with Jackson’s “She’s Got the Rhythm (and I Got the Blues),” and Travis’s “Better Class of Losers.” Speaking with Taste of Country in 2011, Travis said that his tour manager reminded him that Travis and Jackson wrote those two songs in the same day: “We were sitting at the Kentucky State Fair in Louisville, Kentucky and we wrote both of those songs the same day…I’ll tell you what, to write two in one day and both be No. 1s, my percentages usually aren’t that high. I give Alan most the credit. That boy’s a good writer. Man, he’s a good writer.”