Robert Penn's clients include American Ballet Theater, New York Public Library, Aaron Davis Hall, Marlon Saunders, Chimusic, Inc., Thelma Hill Performing Arts Center, N*E*L Productions and Derrick Roberts Productions.

When a client commissions his services, Robert plans the shoot, selects the crew to fit and then works as Director of Photography and/or Editor.

A three-minute film commissioned by choreographer Ronald K. Brown premiered in New York City on October 21, 2003 and has since toured with Evidence, A Dance Company in the United States and abroad. Theodore Bale described Penn’s work as a “stunning digital film” in his March 6, 2005 Boston Herald column.

Robert also produces original digital films for multi-arts performances, gallery exhibition and theatrical presentation. Harlem's Gallery M exhibited four of Robert's short films in 2006. New York State Council on the Arts (NYSCA) awarded Robert a 2006 Individual Artist Grant in Film and Video/New Media Technologies to develop a multi-screen film project that "samples" and "remixes" 1950s educational and public service films.

During 2005, Robert developed several evocative films for Nnenna Freelon's (Chimusic, Inc.) multi-arts tour of music associated with Billie Holiday, who lived from1915 to 1959. His synthesis of archival images and footage evoked facets of U. S. popular culture during those defining decades of the twentieth century, and Black life, in particular.

Dance Camera West, L.A. included one of Robert's documentaries, Connecting Cultures, in its film festival and MetroARTS 13, N.Y.C. programmed another, Evidence of Who We Are, in a cable broadcast hosted by choreographer, Mark Morris. In addition, Anthology Film Archives, N.Y.C. screened Black*Pride, a documentary he co-shot, directed and edited with James Scruggs.