 Carey plays a fictionalized version of himself . Drew is an assistant director of personnel at the Winfred @-@ Lauder department store . Carey explained " I wanted a white @-@ collar job with no authority and a bad boss . Someone to do all the work and get no credit . He could 've worked in a bank , in insurance . " Carey said it was " a no @-@ brainer " on settling on the character , saying " It 's just me . " While Christa Miller was trying out for the role of Drew 's close friend Kate O 'Brien , ABC thought she might be too inexperienced for the role and they asked to see her appearance in the Seinfeld episode " The Doodle " . The episode had yet to be aired and Miller had to beg the show 's co @-@ creator Larry David for a rough cut to show to ABC . Miller went on to secure the role of Kate and Helford considered her to be the only person right for the role . 
