In December 1986, RCA released Oslin's first label single, titled "Wall of Tears." Despite breaking into the top 40, the song failed to become a major hit. In 1987, the label issued the self-penned "80's Ladies," which became her first major hit. Oslin had written the tune several years prior in small chunks over time. "I thought it was one of those show pieces. I never dreamed or thought it would be a single," she stated in 2011. The single peaked at number seven on the "Billboard" Hot Country Songs chart in July and went to number four on the "RPM" Country Singles chart in Canada. It would later win the Grammy Award for Best Female Country Vocal Performance and Song of the Year at the Country Music Association Awards. Oslin became the CMA's first female artist to win the Song of the Year accolade. "80's Ladies" also received a positive response from critics. Steve Huey of Allmusic called the track "anthemic," while Mary Bufwack and Robert K. Oermann called it "the anthem of a generation." Bill Friskics-Warren of "The New York Times" compared its piano sound to that of Jackson Browne. In July 1987, Oslin's debut studio album of the same name was released on RCA. It became the highest-charting album by a female country artist in 20 years, topping the "Billboard" Top Country Albums chart in February 1988. It was also her highest-charting release on the Billboard 200 reaching a peak of 68 in March 1988. It would later certify platinum in the United States for sales over one million copies. Both of the follow-up singles to "80's Ladies" ("Do Ya" and "I'll Always Come Back") reached number one on the country chart.