John Legend joins Shannon Sharpe at Club Shay Shay for a conversation that starts off with a surprise gift from Shannon to John to celebrate his 11th wedding anniversary with his wife Chrissy Teigen. John reflects on the challenge of buying gifts for his wife, Chrissy Teigen, including a memorable year when he gave her a cookbook and a crockpot. He shares the story of how they met during one of his music videos, how he hand-selected her for the role, and when he knew she was "the one." John reveals that Chrissy is the funniest woman he’s ever dated, has great values, and even though her personality is quite different from his, these attributes cemented the idea that she is "the one" for him. He talks about how they made their relationship work even though they slept together on the first date, a moment many couples struggle to get passed. Many consider John and Chrissy "relationship goals," and he discusses how they navigate the ups and downs of their marriage. John explains why it took them so long to get married, recalling his near-botched proposal in the Maldives due to airport security.

John reflects on his upbringing in a big family in Springfield, Ohio. John addresses false comments made by Donald Trump during a debate about Haitian immigrants in his hometown and how those statements created unnecessary conflict. Shannon recalls attending one of John’s concerts and being struck by the way John tells stories during his performances, with his father's influence being a major theme. The conversation turns somber as John discusses how his grandmother’s death deeply affected his family, especially his mother, who struggled with addiction afterward. John shares how being homeschooled and growing up with his cousins shaped him, how entering high school at age 12 and college at 16 made him feel smaller than his classmates, and why he gave up organized sports. He reflects on how lessons from his father helped him through personal struggles, especially during tough times with Chrissy.

John opens up about Chrissy’s life-saving abortion, which made him pro-choice as an adult. John talks about his son’s Type 1 diabetes diagnosis and the challenges that came with it, especially after the repeal of Obamacare made insulin more expensive. He shares the story of how they discovered his son’s condition after he got sick at football camp. On a lighter note, John reminisces about a family trip to Lake Como and how they celebrated their love there, a theme captured in his song “I Don’t Love You Like I Used To.” The song title is meant to trick listeners but reflects his evolving love for Chrissy.

John reflects on his early career, working with Kanye West 20 years ago, and the strong artistic chemistry they shared. He reveals that he originally wrote “Ordinary People” for the Black Eyed Peas and that it was inspired by his parents. He discusses how the name "John Legend" came about, gifted by people in Kanye’s camp, and shares the story of negotiating with a musician and porn producer named Johnnie Legend to avoid a legal dispute over the name. John finishes Part 1 by talking about his work on Lauryn Hill’s The Miseducation of Lauryn Hill.

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