Moving on to film Barry accepted supporting roles in Mask, The Legend of Billie Jean, and as Wolfman in Top Gun. In 1988, he co-starred with Mary Tyler Moore and Lynn Redgrave in the Broadway production of Sweet Sue, in which he appeared nude, and which had a run of 164 performances. The following year he appeared in the drama Warm Summer Rain opposite Kelly Lynch. Barry turned to independent filming and other interests outside of Hollywood. In 1991, he moved to France and rode in a Wild West show. Barry starred, directed, produced, and co-wrote the Cowboys and Indians low-budget thriller Blood Trail which led to no major offers for distribution.