Leonardo DiCaprio Frank Wheeler Kate Winslet April Wheeler Kathy Bates Mrs. Helen Givings Michael Shannon John Givings Kathryn Hahn Milly Campbell David Harbour Shep Campbell Dylan Baker Jack Ordway Richard Easton Mr. Givings Zoe Kazan Maureen Grube Jay O. Sanders Bart Pollock Max Baker Vince Lathrop Max Casella Ed Small Christopher Fitzgerald Party Guest Jonathan Roumie Party Guest Neal Bledsoe Party Guest Marin Ireland Party Guest Samantha Soule Party Guest Heidi Armbruster Party Guest Sam Rosen Party Guest Maria Rusolo Party Dancer Joe Komara Party Dancer John Ottavino Other Actor in the Play Adam Mucci Other Actor in the Play Frank Girardeau Other Actor in the Play Catherine Curtin Woman in Audience Keith Reddin Ted Bandy Ryan Simpkins Ed Small Ty Simpkins Vince Lathrop Dylan Clark Marshall Campbell Kid Jason Etter Vito's Log Cabin Dancer Will Vought Vito's Log Cabin Dancer Dan Zanes The Steve Kovac Band Kristen Connolly Mr. Brace