Shoeless Jeff and Scott Free in San Francisco


Our Vision

Smart Songs formed out of a vision to provide kids and teachers with positive, educational hip hop, that would help make learning fun. The organization was co-founded by artists Shoeless Jeff and Scott Free in early 2008 after several years of rapping together.

Lifelong hip hop fans, they began collaborating on their own songs back in 2001. When they were in high school, they each recorded music individually, honing their craft as rappers. Entering college, they teamed up to create a hip hop band, where they performed live for crowds in concert. The music they made during this era was cool, but not targeted as educational.

This all changed when they performed with their live band, at an inner city Boston high school, in late 2007. The students responded so well to Shoeless Jeff and Scott Free, that they both instantly knew that kids found their music entertaining. This experience led them to begin creating educational based music, without sacrificing what they always considered to be good quality hip hop.

More than a decade later, they are still at it, making songs and videos, that are played in schools throughout the country.


Shoeless Jeff

Jeff, also known as “Shoeless,” was given his nickname by his Little League baseball coach who noticed that he played ball with his socks pulled up like an old-fashioned player. This old-time baseball player was Shoeless Joe Jackson, who once played a game without shoes, entertaining the fans. “Shoeless” Jeff is never afraid to entertain the fans.

Jeff serves as the group’s creative and artistic director and has helped produce many of the songs and videos released to date. He is a graduate from the Honors program at Providence College, where he studied Theatre Arts.


Scott Free

Scott, also referred to as “Scott Free,” was given his nickname because of his ability to kick “free”style rhymes. He also received the name because of his knowledge of America, the Land of the Free. An avid hip hop fan his whole life, he seeks to make songs that people of all ages can appreciate.

Scott serves as the group’s marketing, public relations and finance director. He is a graduate of Providence College, where he double-majored in American Studies and Economics.