[2] From 2005 to 2014, he wrote on hip hop, literature, and painting for the San Francisco Bay Guardian,[3] and has written fiction on unusual sexual practices, like omorashi.
[4] As a hip hop journalist, Caples has been the first write on various Bay Area rappers, including J Stalin,[5] D-Lo,[6] Eddi Projex,[7] Traxamillion, Droop-E,[8] and Shady Nate.
[16] In 2006, Narrow house Recordings released a cd of Caples reading his poems with lo-fi musical accompaniment called Surrealism's Bad Rap.
With Julien Poirier, he has edited Incidents of Travel in Poetry: New and Selected Poems by New York School poet Frank Lima for City Lights Books (2016).
[20] A shortened version of his introduction, "The Lives of Frank Lima," received the Editors Prize for Best Feature Article from Poetry magazine.