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Title: Chapter Eight (11 Dec 2000)
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| Episode cast overview, first billed only: | |||
| Jessalyn Gilsig | ... | Lauren Davis | |
| Chi McBride | ... | Steven Harper | |
| Anthony Heald | ... | Scott Guber | |
| Nicky Katt | ... | Harry Senate | |
| Tom McCarthy | ... | Kevin Riley (as Thomas McCarthy) | |
| Loretta Devine | ... | Marla Hendricks | |
| Joey Slotnick | ... | Milton Buttle | |
| Rashida Jones | ... | Louisa Fenn | |
| Sharon Leal | ... | Marilyn Sudor | |
| Fyvush Finkel | ... | Harvey Lipschultz | |
| Debbi Morgan | ... | Superintendent Marsha Shinn | |
| Rick Gonzalez | ... | Juan Figgis | |
| Bianca Kajlich | ... | Lisa Grier | |
| Stacy Hogue | ... | Kelly O'Toole | |
| Edwin Hodge | ... | Jamaal Crenshaw | |
Buttle meets a beautiful girl, Lisa, who shares his love of Shakespeare. Back at Winslow High, Senate learns that Juan Figgis' mother has been convicted on drug charges and is going to prison. Meanwhile, Lipschultz collapses in class and is rushed to the hospital. Buttle breaks up with Louisa when he realizes he is in love with Lisa, only to find out she is not a 20-year-old Harvard student, but an 18-year-old student at Winslow High. Written by alberta1
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