- Ep: 14
- Sherman, Woman and Child
- Special Guest Voices: Sam McMurray (Cyrus Tompkins), Rhea Perlman (Ardeth)
- Written By: Mike Reiss & Al Jean
- Directed By: Bret Haaland
- Ep: 15
- Siskel & Ebert & Jay & Alice
- Special Guest Voices: Roger Ebert (Himself), Gene Siskel (Himself), Rex Reed (Himself), Gene Shalit (Himself)
- Written By: Jon Vitti
- Directed By: L.H. MacMullan
- Ep: 16
- Lady Hawke
- Special Guest Voices: Morwenna Banks (Olivia), Ricki Lake (Herself), Queen Latifah (Herself)
- Written By: Tom Brady
- Directed By: Rich Moore
- Ep: 17
- A Song For Margo
- Special Guest Voices: Todd Louiso (Johnny), Jimmy Breslin (Himself)
- Written By: Joshua Sternin & Jeffrey Ventimilia
- Directed By: Tom Mazzocco
- Ep: 18
- From Chunk to Hunk
- Special Guest Voices: Rhea Perlman (Ardeth), Tress MacNeille (Julie)
- Written By: Steve Tompkins
- Directed By: Steven Dean Moore
- Ep: 19
- All the Duke's Men
- Special Guest Voice: June Lockhart (Herself)
- Written By: Patric M. Verrone
- Directed By: Chuck Sheetz
- Ep: 20
- Sherman of Arabia
- Special Guest Voice: Tress MacNeille (Boy at Marty's Party)
- Written By: Richard Doctorow
- Directed By: Brian Sheesley
- Ep: 21
- Frankie and Ellie Get Lost
- Written By: Richard Doctorow & Judd Apatow
- Directed By: David Cutler
- Ep: 22
- Dukerella
- Written By: Ken Keeler
- Directed By: Bret Haaland
- Ep: 23
- I Can't Believe it's a Clip Show
- Special Guest Voices: Milton Berle (Himself), Kareem Abdul-Jabaar (Himself)
- Written By: Tom Brady, Richard Doctorow, Al Jean, Ken Keeler, Mike Reiss, Joshua Sternin, Steve Tompkins, Jeffrey Ventimilia, Patric Verrone, Jon Vitti
- Directed By: D.R.L. MacMoortler
| Jon Lovitz ........................... Jay Sherman |
| Nancy Cartwright ................... Margo Sherman |
| Christine Cavanagh ................. Marty Sherman |
| Gerrit Graham ................... Franklin Sherman |
| Doris Grau ................................. Doris |
| Judith Ivey ...................... Eleanor Sherman |
| Nick Jameson .................. Vlada Veramirovich |
| Maurice La Marche .... Jeremy Hawke / Orson Welles |
| Charles Napier ..................... Duke Phillips |
| Park Overall ............................. Various |
| Kath Soucie .............................. Various |
| Russi Taylor ............................. Various |
