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| Directed by | |
|---|---|
 | George Clooney |
| Starring | ||
|---|---|---|
 | Ben Affleck | Uncle Charlie |
 | Tye Sheridan | JR |
| Daniel Ranieri | Young JR |
| Lily Rabe | Mom |
| Christopher Lloyd | Grandpa |
| Max Martini | The Voice |
| Rhenzy Feliz | Wesley |
| Briana Middleton | Sidney |
| Max Casella | Chief |
| Sondra James | Grandma |
| Michael Braun | Bobo |
| Matthew Delamater | Joey D |
| Ivan Leung | Jimmy |
| Danielle Ranieri | Aunt Ruth |
| Kate Avallone | Kathy |
| Mark Boyett | Sidney's Dad |
| Quincy Tyler Bernstine | Sidney's Mom |
| Ezra Knight | Professor Van Dyke |
| David Carl | School Psychologist |
| Shannon Collis | Pat |
| Keira Jo Lassor | Kathy's Daughter |
| Jennifer C. Johnson | Mrs. Williams |
| Michael Steven Costello | NYT Editor |
| Kate Middleton | NYT Personnel Woman |
| Jackson Damon | NYT Copyboy |
| Caroline Bergwall | NYT Copygirl |
| Daniel Washington | Officer James |
| Jenny Eagan | Chief's Wife |
| Steve Gagliastro | Other Customer |
| Annabella Valle | Aunt Ruth Kid #1 |
| Clara Jane Kelly | Aunt Ruth Kid #2 |
| Meara Mahoney-Gross | Aunt Ruth Kid #3 |
| Ron Livingston | Future JR |
| Michael Balzano III | NC Cop |
| Alex Barber | Student in Classroom |
| Julia Bechler | Dickens Bar Regular (Core Group) |
| Keith R Beck | Yale Student |
| Alissa Bourne | Dickens Bar Patron |
| Elijah Carvalho | Classroom Kid |
| Isabelle Charlot | Yale Student |
| Christian Cibotti | A Bar Patron |
| Cody Corelli | Yale Student |
| Daniel George | Classroom Kid |
| Patrick W. Griffin | Ruth's Kid |
| Kimberly Howe | 80's Dickens Waitress |
| Mellanie Hubert | Bianca |
| Chelsea Hueter | 70's Dickens Waitress |
| Dean H. Huh | Restaurant Patron |
| Ian Dylan Hunt | Yale Parent |
| Zack Ignoffo | Boyfriend / Husband |
| Frankie Justin | NYT Editor |
| Ken Kansky | Dicken's Bar Patron, Dicken's Softball Team |
| Elbert Kim | Bowler |
| James J. LaBonte | Dickens Bar Regular |
| Jo-anne Lee | Jimmy's Mother |
| Leslie Luke | Jimmy's Father |
| Jeff MacKinnon | Officer Gulick |
| Billy Meleady | Priest |
| Lily Narbonne | New York Times Reporter |
| Donna Ognibene | Dickens Core Group Patron |
| Addison Oken | Ruth's Daughter |
| David Pridemore | A Customer |
| Melanie Blake Roth | The Voice's Girlfriend |
| Lincoln Rulman | Classmate |
| Mary Ann Schaub | Restaurant Patron / NYC Pedestrian |
| Justin M. Tolliver | NYT Reporter |
| Chloë Trejo | Ruth's Daughter |
| Anastasia Tsikhanava | Waitress |
| Samantha Vita | Ruth's Daughter |
| Mely Wu | Yale Student |
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