Ryan Reynolds as Will Hayes

Abigail Breslin as Maya Hayes

Elizabeth Banks as Emily

Isla Fisher as April

Rachel Weisz as Summer Hartley

Kevin Kline as Hampton Roth

Derek Luke as Russell McCormack

Liane Balaban as Kelly

Annie Parisse as Anne

Nestor Serrano as Arthur

Kevin Corrigan as Rafael

An Nguyen as Ad Exec

Adam Brooks as Bookstore Owner

Emily Wickersham as 1998 Intern

Daniel Eric Gold as Charlie

Adam Ferrara as Gareth

Matthew Mason as Headphone Guy

Rick Derby as Planet Ordon Visitor

Sakina Jaffrey as School Mom

Bob Wiltfong as School Dad

Ryder Chasin as Boy With Book

Fiona Lane as Angry Girl

Dana Eskelson as Angry Girl's Mom

Luis Arriaga as Luis

Melisa McGregor as Bartender

Gerard Bianco Jr. as High School Volunteer

Mel Rocco as High School Volunteer

Stephen Richardson as Pollster

Josh Caras as 1994 Intern

Orlagh Cassidy as Nurse

Max Pomeranc as Campaign Worker

Robert Klein as Robert Klein

Matt Flanders as Ring Salesman

Caryn Osofsky as Café Gitane Night Waitress

Kerri Kwinter as Bookstore Owner

Alexie Gilmore as Olivia

Marc Bonan as Kevin

Amy Šafránková as Café Gitane Day Waitress

Dale Leigh as Bill Clinton

Lauren Norman as Cocktail Server

Leif Riddell as Cab Driver

Blake Benitez as School Kid

Dylan Hartigan as School Kid

Paulina Gerzon as School Kid

Victoria Goldsmith as School Kid