Tom Petty, Garth Brooks Dominate Best Songs of 1989

by Julian Spivey

10."She's Crazy for Leaving" by Rodney Crowell

​Rodney Crowell and his mentor Guy Clark wrote the fun break-up song “She’s Crazy for Leaving” in the early ‘80s and it first appeared on Clark’s 1981 album The South Coast of Texas. Nearly 10 years later in the early part of 1989 the song, off Crowell’s 1988 classic Diamonds & Dirt, would become Crowell’s third consecutive no. 1 (of what would wind up a record-setting five from one album). Crowell’s version of “She’s Crazy for Leaving” is truly one of the underrated country songs of all-time with its infectious fun in spite of lost love. 

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9. "I Sang Dixie" by Dwight Yoakam 

​It’s almost hard to believe, but Dwight Yoakam has only had two no. 1 singles in his career, and both were released in 1988: “Streets of Bakersfield” with Buck Owens and “I Sang Dixie.” “I Sang Dixie, released in late 1988, would top the country music chart in early 1989. The song describes its narrator meeting a dying old man on the busy Los Angeles streets and how the old man longs to be back home in Dixie. It’s a song any Southerner away from home can completely understand. 

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8. "The Road Goes on Forever" by Robert Earl Keen

​Robert Earl Keen’s great outlaw story song “The Road Goes on Forever” debuted on his 1989 sophomore album West Textures and has gone on to become one of the many fan-favorites in his live concert set. The song never became a hit, none of Keen’s songs truly have as he’s remained someone of a cult favorite, despite being one of America’s greatest singer-songwriters of the last 30-plus years. The story of Sonny and Sherry gained a bit more fame in the mid-‘90s when recorded by the country supergroup The Highwaymen featuring Johnny Cash, Kris Kristofferson, Waylon Jennings and Willie Nelson. 

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7. "Runnin' Down a Dream" by Tom Petty

Tom Petty took a bit of a minor risk in 1989 with his first solo album Full Moon Fever, though many members of his band the Heartbreakers did play on the album, but that risk turned into the biggest selling album of his career. “Runnin’ Down a Dream,” which has become of the great rock music driving songs, was the second single off the album in 1989 and would top the Billboard Mainstream Rock chart, while also becoming a top 25 Billboard Hot 100 charter. The song would remain a staple in Petty’s live shows until his death in 2017. 

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6. "I'm No Stranger to the Rain" by Keith Whitley

​“I’m No Stranger to the Rain” was Keith Whitley’s fifth and final single from his 1988 album Don’t Close Your Eyes. It would also be the final single released before his tragic and untimely death in May of 1989 at just 33 years old. “I’m No Stranger to the Rain” hit no. 1 on the country charts just a few weeks before Whitley’s death. The song is incredibly hopeful about being no stranger to the worst and life and coming out the other side. It’s a shame that’s not what would happen in real life for Whitley. This is one of the genre’s most underrated songs of all-time. 

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5. "The Dance" by Garth Brooks

​1989 was the year we were first introduced to Garth Brooks, who would soon skyrocket to becoming one of the biggest smashes in the history of country music. His self-titled debut was released on April 12, 1989 and included three of the greatest songs he’s ever recorded: “Much Too Young (To Feel This Damn Old), “If Tomorrow Never Comes” and “The Dance.” “The Dance” wouldn’t be released as a single until 1990, but we’ll include it here as it was released on the album that year. The song about living life to the fullest because you never know when it’s going to end would become one of Brooks’ greatest hits and won Song of the Year at the 1990 Academy of Country Music Awards. In 2003, CMT named “The Dance” as the 14th greatest country song of all-time. 

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4. "I Won't Back Down" by Tom Petty 

​“I Won’t Back Down” was the very first single ever released by Tom Petty without his band The Heartbreakers and did very well on the Billboard charts hitting no. 12 on the Hot 100 and no. 1 on the Mainstream Rock chart. The song, which would sort of become Tom Petty’s theme song, is an unapologetic ode to never giving up. The song was co-written by Petty and Full Moon Fever producer, fellow Traveling Wilburys member and Electric Light Orchestra leader Jeff Lynne and would see a second life after the devastating terrorist attacks of 9/11 when it turned into a rallying cry four country, especially after Petty performed it on a televised telethon just 10 days after the attacks. 

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3. "Killin' Time" by Clint Black

​Around the middle ‘80s there was a comeback of traditional country music sounds and values led by artists like Randy Travis and Dwight Yoakam, but the second wave of this sound would show up in 1989 with artists like Garth Brooks, Clint Black and Travis Tritt all debuting that year. Brooks has gone on to become the greatest of them all, but nobody had a better 1989 in country music than Black. Black’s debut album Killin’ Time would see the two biggest hits in country music of the entire year with his debut single “A Better Man” being the no. 1 song of the year and his second single “Killin’ Time,” which I believe is the best release of his career, coming it at no. 2. Just that opening guitar lick of “Killin’ Time” is one of the greatest sounds in the history of country music. Black also released the single “Nobody’s Home” in 1989, which might give him the greatest first three singles to start a career of anybody in country music history. 

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2. "Much Too Young (To Feel This Damn Old) by Garth Brooks 

​I know I’m in the minority, but I fully believe “Much Too Young (To Feel This Damn),” the very first single of Garth Brooks career, is the greatest song he’s ever recorded. The song, which talks about how hard life can be for a rodeo man, topped off at no. 8 on the Billboard country chart in 1989. “Much Too Young (To Feel This Damn Old)” is likely the second greatest rodeo song of all-time, just behind George Strait’s 1982 release “Amarillo by Morning.” 

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1. "Free Fallin'" by Tom Petty

Tom Petty absolutely owned the world of popular and rock music in 1989 with his first solo album Full Moon Fever. “Free Fallin’, co-written by Petty and Jeff Lynne, was the album’s third single and its best received topping out at no. 7 on the Billboard Hot 100 chart, the highest charting single of Petty’s career. “Free Fallin’” also became the third straight no. 1 single off the album on the Mainstream Rock chart. Petty’s dominance of 1989 can’t be stressed enough considering this was a time when rock music just wasn’t crossing over to the pop charts as well as it had before. Petty’s three singles from 1989 would all remain staples of his career, so much that they were three of the four songs he and the Heartbreakers would perform during their Super Bowl halftime show in 2008. 

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Let us know what your favorite song from 1989 was ...