The talk show host, now 63, had the star on The Rosie O'Donnell Show back in 2000, when the singer was just 18 years old.

Rosie O'Donnell made a bold statement after Trump's citizenship threat, embracing her American roots with a powerful fashion choice. She also shared which musicals she thinks Trump should watch to ...

Rosie O'Donnell highlighted her slimmer frame in graffiti-print pants, a black tee, an oversized 'New York' blazer, boots and ...