He attended Fine Art school at the University of Maryland, and graduated from the Pratt Institute in 2003.

[4] He has stated that his favorite paintings are those he has done of Brigitte Bardot, in addition to other symbols of sexuality like Anna Karina, Catherine Deneuve and Jane Birkin.

[6] That year he was the first ever featured artist of the first annual New York City Freedom Week, with an exhibition of portraits painted of the survivors of commercial sex exploitation and child soldiery.

[10] In September Penn was then chosen as the sole artist to represent the United States at the Pan-American Games international art exhibition RosaFest.

[12] In November Penn's works became a part of an exhibition in the duplex penthouse of the Trump SoHo which was curated by Indiewalls.