Even before he earned eight Grammy nominations for his debut album Get Lifted—tying with Mariah Carey and his mentor Kanye West for the most nods this year—and before his weepy hit song "Ordinary People" was played during weddings and breakups alike, John Legend was already far from average. At 4, when he was still called Johnny Stephens, he was already asking his mom for piano lessons. He skipped two grades and graduated from high school at 16—at which point he turned down both Harvard and Georgetown. "I was quite the overachiever," admits Legend, 27, who won three Grammys this year. As he gears up for the release of his second album Once Again, the man once nicknamed Doogie (as in TV boy genius Doogie Howser, M.D.) tells PEOPLE's Tiffany McGee what becomes a Legend most.

1 You won't see many typos in his lyric sheets

"I was a spelling bee champ in fourth grade," says Legend, and he has a clipping from a local paper (see next page) to prove it. Homeschooled by his seamstress mother (his dad was a factory worker), Legend outspelled the kids at a private school, then won the Springfield, Ohio, competition. Nervousness got the best of him at regionals. "I knew the word, but I spazzed out for a second and said a totally irrelevant letter at the beginning before I spelled it right. But they don't let you correct yourself." Does he still have the trophies? "I don't remember where they are. That is not hot."

2 He was a musical prodigy

Growing up, "I was surrounded by music," he says. "My brother played the drums, my dad played the drums, my mother sang and directed the choir at church." Legend (left, at age 4) asked to take piano lessons because, he says, "I just saw a piano at my house and figured I should learn how to play it." He may not have been able to reach the pedals, but soon he was playing by ear. He joined his church choir at 7, and by 11 he was directing the group. "I was starting to stand out as a musician," he says. "I was a precocious little kid."

3 He's a PowerPoint pro

After graduating from the University of Pennsylvania with an English degree when he was 20, Legend prepared for a musical career by ... crunching numbers as a management consultant. In his three years at the Boston Consulting Group, "each day was different," he says. "You try to solve problems for your clients by using financial and anecdotal analysis. It all sounds very sexy: PowerPoint and Excel."

4 He's not about the bling

With Kanye West producing his debut, he eventually scored a deal with Sony. "When I got my first big check, I paid [my college loans] off. No more debt!" And then came the shopping spree? Sort of. "I bought a place [in Manhattan]. I just bought some art—some abstract stuff—and some collages are coming too. A friend who works at MoMA is like my art consultant. I just wanted nice stuff that would hold value."

5 He learned how to be a ladies' man

Always younger than his classmates, he didn't have an easy time with girls in school. "I got over it, but it does stunt you a little bit," he says. These days he's got an unfair advantage. He impressed his current girlfriend on their first date: "I was performing at a fund-raiser at the Museum of Modern Art, so I invited her." Usually serenades are "too obvious," so he leaves it to other musicians to set the mood. Here's his playlist for wooing:

VULNERABLE by Marvin Gaye
"It's very romantic. Kind of dark, but sexy romantic."

• NINA SIMONE
"I play it if she's got interesting musical tastes. It's a little bit off—artsy and weird in a good way."

• "GRACE" by Jeff Buckley
"It's kind of intense and passionate. If you want that, you get that."