Janeane Garofalo as Cassie Pines
Episodes 2
The Goodbye Guy
February 7, 2000
2x4
Jerri suffers a devastating loss and can find no sympathy for her grief, though Mr. Jellineck chips in with his special blend of self-important empathy. The Father-Daughter Sack Race plays a pivotal role in this Very Special Episode.
Read MoreThe Last Temptation of Blank
Season Finale
October 2, 2000
3x10
Winona Ryder stars as Fran, the coolest girl in school, who makes a bet that she can make Jerri so cool that even Brent Brooks (Paul Rudd) will ask her out.
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