While Wooldridge’s students were beginners, they weren’t babies, and didn’t want simplistic, babyish stuff. They were drawn in, like tweens and teens are, to funny, creative, and absurd stories with unexpected twists. So, Wooldridge decided to make those kinds of stories himself.
In 2005, Wooldridge began writing his own music for his students. Although he had not even considered seeking a wider audience, it wasn’t long before other teachers found his first website, JamesWooldridge.com.
He renamed the site Señor Wooly in 2009, when he released the music videos Billy la Bufanda and ¿Puedo ir al baño? Both were hits. Since then, he has created numerous well-known musical stories, such as Guapo, Las Excusas, and Sé Chévere, among many others.
Although he is not currently teaching, Wooldridge keeps close ties with the local Spanish educational community, frequently casting Spanish students and teachers to perform in his productions.
Jim Wooldridge lives in Skokie, IL with his wife and two children.