Waldron was featured in a string of commercial roles before landing the part of Becky "Icebox" O'Shea, the only girl on an all-boys football team, in the movie Little Giants.Little Giants is considered her first feature film debut (the film The New Kid, in which she also acted, has never been released). After starring in Little Giants, Waldron went on to play Michael Douglas' daughter in the movie The American President.
Waldron's first television role was in the pilot for CBS's Morning Glory. She then guest-starred on the series Malony in which she played the dramatic role of a teen who had witnessed a murder.
Waldron was nominated for Best Performance in a TV comedy series, Supporting Young Actress category from the Twenty-first Annual Young Artist Awards for 1998-1999 for her role in Ladies Man.