3 Country Music Stars Who Didn’t Make It Big Until Their 30s

Most people believe that you should pack up shop and hit the road if you don’t make it big in music by your ’20s. Even though this seems to be true for many successful musicians, there are exceptions to this rule. There are numerous musicians whose big breaks didn’t come around until rather “late” in the game. Though, this did not stop them, and arguably, it helped them even more.

Rising to fame later in life does many things for one’s career. It gives them more life experience for songwriting, instills a level of maturity amidst the wild forces of fame, and allows for more stability. Arriving late to the game isn’t always a bad thing, and here are three musicians who prove that to be true.

1. Chris Stapleton

Prior to his 2013 launch, Stapleton studied engineering at Vanderbilt, served as the frontman of The SteelDrivers, and was a decorated Nashville songwriter. That said, his ’20s and early ’30s were a series of twists and turns that would go on to lead Stapleton to become a veteran musician before he even went solo.

After years of civilian life, Stapleton entered the country music stratosphere by releasing the single “What Are You Listening To?” in 2013. He was 35-years-old. Props to Stapleton for not only hanging onto the dream for himself but also for his fans, as country music is far better off having Stapleton being an industry giant.

2. Sheryl Crow

She was a teacher, an ad jingle writer, and a background vocalist for Michael Jackson and Jimmy Buffett. Crow has worn many musical hats in her time and seemingly always knew she was destined for solo success. However, it took her years to reach this goal given that Crow did not release her first solo song until she was 31-years-old.

In 1993, Crow released her single “Can’t Cry Anymore.” Following the singles’ success, Crow would go on to release her first album, Tuesday Night Music Club, and solidify herself as a major player for years to come.

3. Sturgill Simpson

If it wasn’t for his wife urging him to try and make a music career, fans might have never known Simpson. Simpson was truly a jack of all trades. Serving in the Navy, waiting tables at Ihop, and managing a freight shipping yard all before he even considered a music career. Simpson was 35 when he released his debut album, High Top Mountain.

Needless to say, his well-lived life has led to some very intriguing stories within his music. Thanks to Simpson’s diverse experience and late entry into country music, the artist has gifted country music with a fresh interpretation of the genre.

Photo credit: Debby Wong