Toby Keith's 'Should've Been a Cowboy' Voted Best Country Song of the '90s

During the 1990s, country music rose to an all-new level of success as people like Garth Brooks, Shania Twain, Trisha Yearwood, and Alan Jackson all became superstars. Despite iconic songs released by those artists, one track that became the "foundation" of a Country Music Hall of Famer's career was voted the "Best Country Song of the ‘90s" by fans.

The Ultimate Decade Debate: A 1993 No. 1 Hit Edges Out the Competition as the Best Country Music Song of the '90s

In October 2025, Ranker updated its article that lets users vote on the "best country songs of the '90s." Based on the input from fans who cared enough to seek out the article and weigh in, Toby Keith's "Should've Been a Cowboy" took the No. 1 slot. It beat out the second track on the list, Garth Brooks' "Friends in Low Places."

Originally released in February 1993, "Should've Been a Cowboy" was the first single from Toby Keith's debut album. It didn't take long for it to reach Billboard's Hot Country Songs chart, where it debuted on March 6, 1993, and spent 23 weeks in total. Just over 33 years ago, on June 5, 1993, the song reached No. 1 on Billboard's Hot Country Songs chart, where it stayed for two weeks.

'It's the Foundation for Me of Everything': The 1993 Masterpiece That Built a Hall of Fame Career

In June 2018, Toby Keith was interviewed by The Oklahoman about the 25th anniversary of his first hit, "Should've Been a Cowboy," reaching No. 1. During that discussion, the country music superstar spoke about how the iconic song was the basis of the rest of his legendary career. "It's the foundation for me of everything."

He also explained that he kept the track in the spotlight throughout his lengthy career. "I'm giving that song its due. … I've never played a show that I didn't play that song. I've probably got 15 or 20 No. 1s I don't play, and I've probably got 20 or 30 top 10s I don't play. I do a two-hour show every night, and I play a lot of hits and a lot of No. 1s. But I've never not played that song – no matter what."

As he noted during that interview, the country music star released a staggering number of hits before he passed away in February 2024 from stomach cancer. As a result of everything he accomplished, Toby Keith was then posthumously inducted into the Country Music Hall of Fame in October 2024.

Next: 51 Years Ago Today, a 1975 Country ‘Anthem for Hard-Working, Small-Town Folks Everywhere' Hit No. 1

This story was originally published by Men's Journal on Jun 18, 2026, where it first appeared in the News section. Add Men's Journal as a Preferred Source by clicking here.

2026 The Arena Group Holdings, Inc. All rights reserved.

This story was originally published June 18, 2026 at 7:15 AM.