 Rachel Dratch , longtime comedy partner and fellow Saturday Night Live ( SNL ) alumna of Fey , the latter who was the show 's head writer from 1999 until 2006 , was originally cast to portray Jenna Maroney . Dratch played the role in the show 's original pilot , but in August 2006 , actress Jane Krakowski was announced as Dratch 's replacement . Executive producer Lorne Michaels announced that while Dratch would not be playing a series regular , she would appear in various episodes in a different role . In this episode , Dratch played Pamela Smew , a group therapist in charge of sensitivity training between Tracy and Toofer . This was Dratch 's fifth appearance on the series . Various other cast members of SNL have appeared on 30 Rock . These cast members include : Chris Parnell , Fred Armisen , Kristen Wiig , Will Forte , Jason Sudeikis and Molly Shannon . Fey and Tracy Morgan have both been part of the main cast of SNL . Chris Hansen of Dateline NBC 's television segment To Catch a Predator appeared as himself in this episode , in which he confronts Dennis on To Catch a Predator . 
