Growing up in Springfield, Legend was one of four children with a musically inclined family. His father played the drums, his mother sang and ran the church choir and his grandma played the organ, Shepard said.
Legend explained that the church was where he was exposed to music.
“The church is one of those places where you can still be exposed to a lot of music and music particularly in a black church is so central to the experience that R&B singers are always going to come from there,” Legend said.
He added that all of his band members grew up playing in churches.
Another pivotal experience Legend discussed was transitioning from homeschooling to high school.
Legend explained that he was homeschooled through kindergarten and when it was time for him to go to first grade at Springfield Christian School, his mother said he was “too smart for first grade.” After taking a few tests and testing at a third and fourth grade level, the school placed him in second grade.
“After two years at the Christian school, we couldn’t afford it, so they brought me back home,” Legend said.
He was homeschooled for fourth, fifth and sixth grades.
Once his parents divorced, Legend said he went to public school. Instead of going into seventh grade, he was tested again and placed into eighth grade.
“I turned out fine, but I definitely think it was a challenge and I wouldn’t want to put my kids through that,” Legend said.
He explained that because he skipped two grades, he was in the same grade as his older brother, Ron Stephens.
“My brother was always there with me,” Legend said. “He took care of me and made sure nobody messed with me.”
Legend added, “We’ve been together through everything starting with the first day when I was born.”
A picture of the two brothers appeared in the newspaper the day Legend was born because his brother was one of the first siblings that were allowed to come inside the hospital, Legend explained. This was a new program at the hospital.
Legend’s closeness with his brother continues as Stephens is his personal barber that travels on the road with him.
Following his graduation in 1999, Legend went to the University of Pennsylvania and began writing, producing and recording his own music until he was introduced to hip-hop artist Kanye West, by his college roommate.
From there, his career took off. Legend is now the first African-American man to be an EGOT winner. He has won all four awards in the entertainment industry - Emmy, Grammy, Oscar and Tony.
Legend told Shepard that “music was that thing for me that just helped me navigate a lot of social circumstances where otherwise I would of been hopeless.”
He added that music helped him connect with other people and made him come out of his shell. .
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