Newlyweds Rick and Lily cope with the angst of his beleaguered 18-year-old son, Eli (Shane West), busted for marijuana possession. Stephanie: Kay Lenz. Karen: Susanna Thompson. Christie: Jennifer Crystal Foley. Coop: Adam Brody. Judy: Marin Hinkle. Lily: Sela Ward.
Employment decisions vex Lily, who's torn between working for Judy or a prominent radio figure (Paul Dooley); Grace has a run-in with her creative-writing teacher (Eric Stoltz). Will Gluck: Mark Valley. Tiffany: Ever Carradine. Judy: Marin Hinkle. Grace: Julia Whelan. Jake: Jeffrey Nordling.
The return of the enigmatic artist Sam Blue (Steven Weber) has professional ramifications for Rick and personal repercussions for Judy, who has bittersweet memories of their affair. Tiffany: Ever Carradine. Colin Fleischer: Saul Rubinek. Jake: Jeffrey Nordling. Dr. Lerner: David Kipper. Judy: Marin Hinkle.
Competition for a major role in a school play pits Grace against Jessie; concern over the blossoming affair between Judy and Sam (Steven Weber) preoccupies Rick and Lily. August Dimitri: Eric Stoltz. Cynthia: Ashlee Turner. Ajay: Ira David Wood. Alexa: Natasha Gaty. Judy: Marin Hinkle. Grace: Julia Whelan. Jessie: Evan Rachel Wood.
An unexpected, on-air role at the radio station exhilarates Lily and disquiets her family; the prospect of a first date flusters Jessie and worries her mom and dad. Les: Paul Dooley. Mr. Dimitri: Eric Stoltz. Dr. Sherri Snyderman: Meagen Fay. Tad: James Lafferty. Dr. Rosenfeld: Edward Zwick. Gayle: Miriam Flynn. Jessie: Evan Rachel Wood.
Tiffany's pregnancy vexes Jake, who's beset by Zoe to participate in a baby shower that's being organized by Lily to cheer up the dispirited mother-to-be (Ever Carradine). Brandy: Mariah O'Brien. Lamaze Teacher: Amy E. Wieczorek. Vic: Gunther Jensen. Dr. Lu: Susie Park. Jake: Jeffrey Nordling. Zoe: Meredith Deane.
A tumultuous Thanksgiving finds Grace and Jessie feuding, Rick stressing out at work and Lily coping with a plumbing problem that's a prelude to a kitchen disaster. Mr. Dimitri: Eric Stoltz. Raoul: Benito Martinez. Alexa: Natasha Gaty. Sam Blue: Steven Weber. Tiffany: Ever Carradine. Karen: Susanna Thompson. Lily: Sela Ward.
Intimacy matters disquiet Rick and Lily, who face a trying period of adjustment, and perplex Judy and Sam (Steven Weber), who reassess their mercurial relationship. Tad: James Lafferty. Katie: Mischa Barton. Steven Slater: Edward Atterton. Judy: Marin Hinkle. Jessie: Evan Rachel Wood. Eli: Shane West.
Scenes from a high-school production of Shakespeare's “As You Like It” frame off-stage anxieties perplexing Grace, Jessie and Eli, who loses his job and drifts into melancholy. Mr. Dimitri: Eric Stoltz. Katie: Mischa Barton. Sarah: Lizzy Caplan. Tad: James Lafferty. Alexa: Natasha Gaty.
'Twas the night before Christmas, and at the Sammler house the one that's stirring the most is the unborn child of Tiffany (Ever Carradine), who goes into labor while a blizzard rages. Tami: Rosalind Chao. Les Cresswell: Paul Dooley. Jamie: Jacob Smith. Sam Blue: Steven Weber. Edith: Danielle Wolf. Jake: Jeffrey Nordling. Grace: Julia Whelan.
Flashbacks in the series' interview style recall a telling incident in the lives of Rick, Karen, Sam Blue's estranged wife (Jane Sibbett) and Sam himself, who rues another dalliance. Melissa: Rebecca McFarland. Sam: Steven Weber. Judy: Marin Hinkle. Karen: Susanna Thompson. Grace: Julia Whelan.
Depression overwhelms Karen (Susanna Thompson), whose anxieties, mood swings and erratic behavior disquiet Jessie and Eli---and foreshadow calamity. Katie: Mischa Barton. Dr. Solomon: Richard Kramer, who wrote the script. Adam: Steven Mayhew. Jessie: Evan Rachel Wood. Eli: Shane West.
Hospitalized Karen undergoes an arduous rehabilitation that's framed by Jessie's acute anxieties, Rick's emotional responsiveness and Eli's increasingly erratic behavior. Henry: D.B. Woodside. Katie: Mischa Barton. Dr. Rosenfeld: Edward Zwick. Lloyd: James Eckhouse. Alexa: Natasha Gaty. Karen: Susanna Thompson. Eli: Shane West.
Tensions arise between Jessie and her best friend, Katie, who's outed as a lesbian; and between Grace and Mr. Dimitri (Eric Stoltz), the drama coach with a secret past. Katie: Mischa Barton. Tad: James Lafferty. Les: Paul Dooley. Dr. Rosenfeld: Edward Zwick. Grace: Julia Whelan. Jessie: Evan Rachel Wood.
Tensions arise in the relationship between Judy and Sam (Steven Weber), due mostly to his peeved, preteen son; the responsibilities of new fatherhood test Jake's roving ways. Tiffany: Ever Carradine. Jamie: Jacob Smith. Jeannine: Jane Sibbett. Kenny: John Lehr. Gerri: Joy Stevens.
Patrick Dempsey returns as Lily's sensitive, disturbed brother Aaron, who's entranced by a volatile patient (Ally Sheedy) whom he met in their board-and-care residence. Herb Miller: Robert Prosky. Shelley: Winnie Holzman. Lily: Sela Ward. Judy: Marin Hinkle. Grace: Julia Whelan.
The prospect that Grace may be romantically involved with her creative-writing teacher (Eric Stoltz) troubles Lily, infuriates Jake and imperils the career of the instructor. Les: Paul Dooley. Alexa: Natasha Gaty. Katie: Mischa Barton. Ms. Conway: Lee Garlington. Mr. Brooker: Darius Dudley.
Bonnie Bartlett plays the Brooks family matriarch, a proud yet failing woman who reawakens memories that Lily shares in dreamlike sequences with her late father (Paul Mazursky). Tiffany: Ever Carradine. Zoe: Meredith Deane. Jake: Jeffrey Nordling. Judy: Marin Hinkle.
In the series finale, Rick and Lily face difficult career decisions; Karen enters into a new romance that intrigues yet troubles her; and Jake, despite anxieties, proposes to Tiffany. Colin: Saul Rubinek. Henry: DB Woodside. Les: Paul Dooley. Katie: Mischa Barton. Tiffany: Ever Carradine.