Selma Blair as Vi

Leo Fitzpatrick as Marcus

Robert Wisdom as Mr. Scott

Maria Thayer as Ami

Angela Goethals as Elli

Devorah Rose as Lucy

Nancy Anne Ridder as Joyce

Steve Rosen as Ethan

Aleksa Palladino as Catherine

Mary Lynn Rajskub as Melinda

Tina Holmes as Sue

Paul Giamatti as Toby Oxman

Mike Schank as Mike the Cameraman

Xander Berkeley as Mr. DeMarco

Mark Webber as Scooby Livingston

John Goodman as Marty Livingston

Julie Hagerty as Fern Livingston

Jonathan Osser as Mikey Livingston

Noah Fleiss as Brady Livingston

Lupe Ontiveros as Consuelo

Jessica Dunphy as Cheryl

Nick Maltes as Esposito

Steve Railsback as Mr. Kirk

Crista Moore as Elizabeth St. Clair

Franka Potente as Toby's Editor

Andrew Marantz as Stanley

Conan O'Brien as Himself

Frederick B. Owens as Football Coach

Barry Jordan as Dr. Barry Jordan

Robin Goodman as Dr. Robin Goodman

Eric Nieves as Dave

Marisa Redanty as Onlooker #1

Ilana Levine as Onlooker #2

Jennifer Elise Cox as Musical Theatre Actress (uncredited)

Pat Kiernan as TV News Announcer (voice) (uncredited)

Gina Priano as Student (uncredited)

Tom Schimmels as Man in Toby's Apartment (uncredited)

Jim Titus as Football Player (uncredited)