Country Cuts: 6 Huge Hits from 1988

hank jr

Country music in the late 80’s was a dynamic scene, featuring a fabulous mixture of grizzled veterans and new blood. Rising stars such as Randy Travis and Dwight Yoakam shared time on the charts with stalwarts such as Haggard and Milsap. It is important to note that this was country music “BG”, or Before Garth. The legendary “Class of ‘89”, which includes Garth Brooks, Clint Black, Alan Jackson, and Travis Tritt, catapulted country music into a new stratosphere. Over the next thirty years, the Class of ’89 accounted for 64 #1 country hits. Brooks has become one of the highest selling solo music artists of all time. But in 1988, the country music landscape looked different.   

One year before being upended by Brooks and Co., Music City was on the cusp of cultural change. Country’s prodigal son/bad boy Hank Williams Jr. was named Entertainer of the Year by the Academy of Country Music and the Country Music Association. It was also an incredible year for the ladies. Mother-daughter team The Judds swept the Top Vocal Duo categories while Roseanne Cash charted four #1 singles, more than any other artist.   

The country singles charts of thirty-five years ago displayed beautiful parity due to the awesome depth of both emerging and established talent. Just four songs held the top spot for multiple weeks. It was an even musical playing field, before the genre got above its raisin’. Surely the last remnants of an era, but one filled with incredible music. Here are six of the most successful songs and artists to fill the country charts in 1988.     

“Eighteen Wheels and a Dozen Roses” – Kathy Mattea

Hitting #1 in May, this Kathy Mattea number has survived as a sentimental classic. It was the first song to spend more than one week at the top position and Mattea’s second #1 of the year. “Eighteen Wheels and a Dozen Roses” was written by brothers Gene and Paul Nelson and remains Mattea’s signature tune. It won ACM song of the year, ACM single of the year, and CMA Single of the Year.

“I Told You So” – Randy Travis

“I Told You So” reached the chief spot in mid-June. It was Randy Travis’ second of his three #1 hits in the year. It was also the second song to spend more than a single week at #1. From his second studio album, the tune was penned by Travis and helped secure him the award for CMA Male Vocalist of the Year. Carrie Underwood covered the song for a 2007 album, peaking at number two.

“I’ll Leave This World Loving You” – Ricky Van Shelton

Written by Wayne Kemp and Mack Vickery, Kemp recorded this song on MCA Records in 1974. By the time the tune reached Shelton in 1988, it had been covered by both Ronnie Milsap and Mel Street, to marginal fanfare. “I’ll Leave This World Loving You” hit #1 in late November and was the third single to spend two weeks in that position. It capped an amazing year for Ricky Van Shelton that included three #1 songs and the CMA Horizon Award. 

“When You Say Nothing at All” – Keith Whitley

This song was budding superstar Keith Whitley’s second #1 in 1988. The tune was written by Nashville legends Paul Overstreet and Don Schlitz. “When You Say Nothing at All” was the last song of the year to serve multiple weeks at the top of the charts. It made #1 in late December, finishing out the year at that position. Less than six months later, Keith Whitley was found dead at the age of 34 from alcohol poisoning.   


“Hold Me” – K. T. Oslin

This song is one of the most celebrated from 1988. Released in September, “Hold Me” was written and performed by K. T. Oslin, appearing as the second single off her second album. It became the first #1 song of 1989 and was the singer’s third #1 overall. The tune was emphatically praised, as was Oslin. “Hold Me” won two Grammy awards including Best Country Song. Oslin took home both CMA Female Vocalist of the Year and ACM Top Female Vocalist.


“Streets of Bakersfield” – Dwight Yoakam and Buck Owens

Written by Homer Joy, this tune was originally released by Buck Owens in 1973. In 1988, burgeoning star Dwight Yoakem decided to reconfigure and rerecord the tune as a duet. Yoakem, a passionate Owens acolyte, talked the venerated legend out of semi-retirement and into performing with him on the track. New elements were added such as Mexican influenced accordion provided by master musician Flaco Jiménez. Also a classic music video, “Streets of Bakersfield” reached the top slot in mid-October. It was Yoakem’s first career #1 song. It was Owens’ first #1 song since 1972.  

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