He is the son of New York businessman and lawyer Arthur Penn, who led the acquisition of the Capital Markets Assurance Corporation from Citicorp.

Films that Penn has been involved in writing include Last Action Hero, X2, X-Men: The Last Stand, and Elektra.

Penn is also a jury member for the digital studio Filmaka, a platform for undiscovered filmmakers to show their work to industry professionals.

[3] In July 2012, Avatar Press released the first issue of Penn's first comic book, Hero Worship.

It centers on Zenith, an indestructible hero who has fans following every disaster, trying to catch a glimpse of the ultimate celebrity and risking their own lives in the process.