In a memorable Club Shay Shay episode, Shannon Sharpe kicked things off by surprising John Legend with an 11th-anniversary gift to celebrate his marriage with Chrissy Teigen. Legend shared laughs over his own gift-giving missteps, recalling the year he gave Chrissy a cookbook and a crockpot. Their love story is a testament to fate, beginning on the set of one of Legend’s music videos, where he felt an instant connection to Chrissy’s humor and values and knew early on that she was “the one.”
The conversation unfolded to reveal the more personal side of their journey, including their first date, when they decided to spend the night together, their delay in tying the knot, and the Maldives proposal that Legend says didn’t quite go as planned.
Legend looked back on his roots, growing up in a big family in Springfield, Ohio, where he was homeschooled and entered high school by age 12. Though smaller than his peers, which led him to leave organized sports, Legend’s father’s guidance became a lasting influence, especially in handling challenges in his marriage with Chrissy. He also spoke openly about their difficult experiences, including Chrissy’s life-saving abortion and their son’s Type 1 diabetes diagnosis, obstacles that were made more challenging following the repeal of Obamacare. Reflecting on happier memories, Legend recalled a family trip to Lake Como that sparked the inspiration for his song “I Don’t Love You Like I Used To.”
The conversation turned to Legend’s early music career, where he shared anecdotes about working with Kanye West and the origin of his iconic stage name. He noted how “Ordinary People,” now one of his most beloved hits, was initially written for the Black Eyed Peas and spoke warmly of collaborations with icons like Lauryn Hill. On future aspirations, Legend expressed hopes of working with Beyoncé and Adele, while also sharing his admiration for DJ Khaled’s ability to unite artists across genres.
Reflecting on his biggest songs, Legend singled out “Ordinary People” as a personal favorite, though he admitted “All of Me” is his most commercially successful track. Inspired by Billy Joel, he first sang it to Chrissy while they were engaged. Legend discussed his career evolution, his recent choice to sell his music catalog, and his concerns over the decline in church-rooted musical talent—a legacy he hopes can be rekindled.
When looking toward the upcoming presidential election, Legend praised Vice President Kamala Harris for her potential impact on underrepresented communities, noting her background at an HBCU and as California’s Attorney General. He voiced concern over Donald Trump’s influence on America’s social landscape, expressing optimism that leaders like Harris could bring meaningful change if she ascended to the presidency.
