Despite being a winning coach on The Voice, John Legend hasn't always had success with singing competitions.

The Grammy-winning artist appeared on The Tonight Show Starring Jimmy Fallon Monday where he revealed that he was once rejected by popular talent show Star Search.

"I wanted to be on Star Search so badly. I used to grow up watching Ed McMahon, and so many great artists actually came through Star Search," Legend told Fallon. "I would watch the show and I was like, 'I wanna be on there, I deserve to be on there!' "

Legend, 42, said that he was so passionate about the show that he entered a competition as a kid when Star Search came to his local mall.

"My local mall, it was called the Fairfield Commons Mall, outside Dayton, Ohio, they had a local Star Search competition and if you won the local competition they would send your tape to national Star Search," he explained.

The "All of You" artist said he ended up winning the competition but was never asked to move forward with the show.

"I won the local Star Search competition, they sent my videotape to the national Star Search, and I never got a call back," he said. "That was that."

While EGOT-winner didn't get his shot on the singing show, Legend said he was at least given a consolation prize.

"I did get a $500 shopping spree at the new mall and I bought a lot of clothes, so I was happy," he added to Fallon.

Legend recently opened up about his early love for music in an episode of Facebook Watch's Forward: The Future of Black Music in celebration of Black History Month.

While chatting with Grammy-nominated rising star and Rhythm + Flow winner D Smoke, Legend said he's been perfecting his craft since age 4.

"When did you first start playing the keys?" Smoke (né Daniel Farris), 35, asked. "When was the first time you sat down and was like, 'Okay, I'm gonna do this for myself?'"

"Probably a lot like you, we had a piano in our house growing up," PEOPLE's former Sexiest Man Alive recalled. "I saw it there and I was like, 'Well, obviously it's meant to be played.'"

That's when the "Bigger Love" hitmaker decided it was time to start learning. "I was like, 'Mom, I wanna take piano lessons.' I was 4 years old," he said. "I started taking classical piano lessons at 4 and then my grandmother was our church organist and she started to show me how to play gospel music when I was like 7 or 8."

Eventually, he added, "I had gotten to the point where I could play for the church." But Legend quickly quipped, "I wasn't that great back then."

The icon credits his childhood influencers for molding him into artist he is today. "That's really where I became a musician. You know the feeling? I wouldn't be where I am without that experience," he told D Smoke, who agreed.

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