Both Roberts and Richie were born in Tuskegee, where Roberts' father served as a Tuskegee Airman.
Richie grew up in the Alabama town, while Roberts and her family moved away shortly after her birth due to her dad's military career.
When the four-time Grammy winner and the "GMA" co-anchor reunited recently in Tuskegee, they reminisced about how Richie's mom, a school teacher, even taught some of Roberts' three siblings in a local school.
"This is more than just a birthplace," Richie told Roberts. "We grew up in history, and so things that people are trying to read about, it was every day."
Tuskegee, a city of around 9,000 people, is home to not only the Tuskegee Airmen -- the country's first African American military pilots -- but other history-making figures including Rosa Parks and Booker T. Washington as well.
Both Roberts and Richie said they remember learning in their childhood that "failure is not an option."
"We grew up on this military base, if you will, and so they had a standard for all of us," Richie said. "Failure is not an option."
Roberts said that phrase was common in her youth, saying, "My daddy used to say that. He used to say it was not an option."
Roberts' father, Col. Lawrence E. Roberts, earned his master's degree in Tuskegee and was an award-winning pilot who served in three wars -- World War II, the Korean War and the Vietnam War -- according to his biography.
It was in World War II that he and other African American pilots flew combat missions as the Tuskegee Airmen for the U.S. Army Air Forces. The legendary airmen, including support staff, are widely regarded as being among the Air Force's finest.
For Richie's visit to Tuskegee with Roberts, he brought his fellow "American Idol" judges Katy Perry and Luke Bryan to show them the accomplishments of his hometown, including the history of the Tuskegee Airmen. "American Idol," which will premiere its 22nd season next year, also hosted hometown auditions in Tuskegee.
"I get to show off Tuskegee," Richie said during his visit. "To bring it back here for me is a chance to get them to understand the roots of another kind of Black America that people don't get to hear and talk about every day."
In addition to showing them his childhood home, Richie also returned to what is now known as Tuskegee University, where he spent most of his beloved early years.
Looking back at his childhood in Tuskegee, Richie, who is preparing for the launch of his new Las Vegas residency, said he never could have imagined his lasting success, saying, "Not in my wildest dreams."
"We just talked about the airmen, Ph.D.s and doctors, and lawyers and planes and flying and stuff, and here I am talking about, 'We're the 'Black Beatles' and we're gonna take over the world,'" Richie said of getting his start in music. "Five years later, we hit. But what I'm surprised at is that it kept going."