A self-help advocate struggles to put his dysfunctional family in its place.
| Actor | Role |
|---|---|
 Al FrankenStuart Smalley | Stuart Smalley |
 Laura San GiacomoJulia | Julia |
 Vincent D'OnofrioDonnie | Donnie |
 Shirley KnightMom | Mom |
 Harris YulinDad | Dad |
 Lesley BooneJodie | Jodie |
| JJohn Link GraneyKyle | Kyle |
| MMarjorie LovettAunt Paula | Aunt Paula |
 Walter RoblesSmalley Uncle | Smalley Uncle |
 Erik CordSmalley Uncle | Smalley Uncle |
| DDenver MattsonSmalley Uncle | Smalley Uncle |
| GGrant HooverYoung Stuart | Young Stuart |
| CCory MilanoYoung Donnie | Young Donnie |
 Michelle HornYoung Jodie | Young Jodie |
| HHarris LaskawyMr. Dimmit | Mr. Dimmit |
| TTom DuganAjax Spokesman | Ajax Spokesman |
 Camille SaviolaRoz Weinstock | Roz Weinstock |
 Bess MeyerLaurie | Laurie |
 Julia SweeneyMea C. | Mea C. |
 Patrick KerrMakeover Artist | Makeover Artist |
 Aaron LustigFred | Fred |
 Fred ApplegateCarl | Carl |
 Darrell LarsonJerry | Jerry |
 Dakin MatthewsIntervention Counselor | Intervention Counselor |
 Jeffrey JosephLawyer | Lawyer |
| MMarte Boyle SloutMadelyn Doyle | Madelyn Doyle |
 Joe FlahertyCousin Ray | Cousin Ray |
 Robin DukeCousin Denise | Cousin Denise |
 Lewis ArquetteCemetery Official | Cemetery Official |
 Mike HagertyCop | Cop |