Pickering was an old friend of playwright
Larry Shue and often worked with him. On stage, James played the role of Woody in Shue's early play "Grandma Duck Is Dead," documentation of which is held in the 1978-1979 file in the University of Wisconsin-Milwaukee's Manuscript Collection. Their Collection and website have photos of Pickering during a 1979 production, at the Milwaukee Repertory Theater, of this farcical one-act play about the antics of graduating seniors in a college dormitory in 1968.
Famously, Pickering also played the hilariously annoying Rick Steadman - a house-guest-from-hell who comes for dinner, but plans to move in for an indefinite stay - in Shue's immensely popular play "The Nerd" (photos again can be found online). This character-based comedy toured the U.S. and abroad and, in the 21st century, still enjoys revivals in college and repertory companies. The play was adapted for German television as "Laus im Pelz" (1987), with the role going to
Dieter Hallervorden. Shue dedicated the published playbook of "The Nerd" to James Pickering.
