Kathie Lee Gifford, reflecting on her extensive career, described herself as someone who often felt like a surprised observer of historical events, likening herself to the character Waldo. This sentiment extended to her performance at President Ronald Reagan's second inauguration in 1985. "It's like, why in the world is this skinny little kid from Bowie, Maryland singing for the president?" Gifford recalled.
During that inauguration, Frank Sinatra, present at the event, offered a brief but impactful endorsement of Gifford's singing. "The kid can sing," Sinatra reportedly said, a comment Gifford found encouraging during times of critical reviews.
Gifford also contributed to the soundtrack of the biopic "Reagan," starring Dennis Quaid and Penelope Ann Miller, which was re-released to coincide with America's 250th anniversary. She co-wrote and recorded the duet "I Knew It Would Be You" with country singer Josh Turner. While praising Quaid's performance as "Oscar-worthy," Gifford expressed disappointment that she believed he would not receive due recognition from Hollywood due to the film's subject matter.
She characterized the film primarily as a love story between Ronald and Nancy Reagan, noting the palpable adoration between the couple. Gifford shared a personal connection to Reagan through her late husband, Frank Gifford, who was a friend of the president. She recalled Reagan's earlier political affiliations and his role as president of the Screen Actors Guild (SAG), describing him as a "moderate, literate and good man."
Gifford also recounted encounters with other notable figures, including Mikhail Gorbachev, and expressed a generally fearless outlook on life, rooted in her faith. She adheres to the advice of Reverend Billy Graham, who cautioned against political involvement in entertainment, to avoid alienating audiences. Gifford stated, "I'll take someone's kindness any day over their opinion." She affirmed her appreciation for the U.S. Constitution and the freedoms it guarantees, including the right to individual thought, worship, and voting, stating that citizens "deserve the government we vote for."