Ben Stiller as Josh Schrebnick

Naomi Watts as Cornelia Schrebnick

Adam Driver as Jamie Massey

Amanda Seyfried as Darby Massey

Charles Grodin as Leslie Breitbart

Maria Dizzia as Marina

Adam Horovitz as Fletcher

Dree Hemingway as Tipper

Brady Corbet as Kent Arlington

Matthew Maher as Tim

Peter Yarrow as Ira Mandelstam

Bonnie Kaufman as Ira's Wife

Hector Otero as Frank

Matthew Shear as Benny

Annie Baker as Elise

Quincy Tyler Bernstine as Pepper

James Saito as Dr. Nagato

Deborah Eisenberg as New School Woman

James Manzello as Music Class Band

Laura Hankin as Music Class Band

Stoddard Blackall as Music Class Band

Ariel Bethany as Music Class Band

Juan Torriente as Leslie's Colleague

Dean Wareham as Shaman

Erin Byrne as Ayahuasca Woman

Lily Thorne as Party Guest

Matthew Kaplan as Party Guest

Danielle Slavick as Party Guest

Greg Keller as Party Guest

Nico Baumbach as Party Guest

Liz Stauber as Kent's Sister

Ryan Serhant as Hedge Fund Dave

Wyatt Ralff as Louis

John Wildman as Red Carpet Coordinator

Roberto Pascotto as Tribute Guest

Adam Senn as Bartender

Guy Boyd as Bar Patron

Peter Bogdanovich as Speaker

Jake Perlin as Jake (uncredited)

Greta Lee as Sundance Interviewer (voice)

Scott Rudin as Party Guest (uncredited)