When was Riley Green on Redneck Island? Country star recalls winning $100,000 and planning retirement

Prior to Riley Green establishing himself as one of country music's emerging stars, he was on a reality television show and took home $100,000. It was long before his songs like "There Was This Girl" and "I Wish Grandpa Never Died" became hits.

Green was a contestant on the CMT reality competition Redneck Island hosted by WWE great Steve Austin. The series, which debuted in 2012, was like Survivor and the contestants were stranded on an island, with 24 of them competing in physical challenges for a chance to win $100,000.

Green first joined Redneck Island in season four. At the time, he was still an up-and-coming musician from Alabama, playing shows at places like Flora-Bama while attempting to further his career.

Do you remember @RileyGreenMusic's big win on reality TV? https://t.co/cypqQQGbaj

— Taste of Country (@TasteOfCountry) September 4, 2025

Riley Green has stated that the producers approached him at one of the shows and told him to audition for the show. He first hesitated but later thought it could be a good way to get his music in front of more people.

"I did it because I thought it could help my music, and I believe it will. If 40,000 people watch it and they mention my music, I believe it’s worth it.” he told The Anniston in a later interview.

Green's first time did not last long, he was eliminated early in Season 4, but the show invited him back the next year for Season 5 in 2016.

Green's second time on Redneck Island was much more successful. With his partner Becky Andrews, Green completed all the tough challenges throughout the season and made it to the finale episode. They won the show and received a total of $100,000 that was split between the two of them.

Riley Green opens up about the lessons learned from the reality TV appearance

To Riley Green, at the time, $50,000 was supposedly a life-changing amount of money. He would later confess that he thought that amount would “retire” him.

"I thought I was just gonna retire after that. I thought $50,000 was all I'll ever need," Riley Green said on the Zach Sang Show.

But the experience also woke him up to the reality of money. "I found out what taxes are pretty quick," he said. "And the IRS found out I was a person," he chuckled, suggesting that he was compensated for the small-town gigs he was doing at his age and understood cash before his time as a singer.

Apart from the money, Green said that he got to see the inner workings of the entertainment industry. He explained that producers would often cue contestants during exit interviews to create plotlines for the show.

Riley Green opens up about his hesitation to sing in front of people in his twenties during his recent appearance on the Zach Sang Show. pic.twitter.com/r7YOJRfMQI

— Country Chord (@CountryChord) September 4, 2025

Initially, his response as to how he handled these interviews was to give the producers one-word answers, but eventually Green learned that playing along made the process easier.

"I realized if I said what they wanted, I could get out of those interviews faster," Green said. "So I started getting good at interviews, you know: What are we trying to paint here? What picture?" he added.

Green also reflected on how the show depicted him, specifically in his bio, calling him a "career drinker." His mother did not appreciate that, but Green accepted that as part of the reality TV persona at that time. He thinks it was a stepping stone, even though it did not create a fanbase right away, it did give him lessons and exposure.