Adam Sandler Max Simkin Method Man Leon Ludlow Dustin Hoffman Abraham Simkin Steve Buscemi Jimmy Melonie Diaz Carmen Herrara Ellen Barkin Elaine Greenawalt Dan Stevens Emiliano Elli Goldman Sondra James Anna O'Hara Dascha Polanco Macy Lynn Cohen Sarah Simkin Fritz Weaver Mr. Solomon Adam B. Shapiro Schneider Yul Vazquez Marsha Evan Neumann Neumann Allen Lewis Rickman Kessler Donnie Keshawarz Pinchas Simkin Ethan Khusidman Herschel Simkin Kim Cloutier Taryn Stuart Rudin Old Bearded Man Wayne Wilderson Young Preppy Man Craig Walker Danny Donald Cliff Samara Indian Man Stephen Lin Chinese Guy Miles J. Harvey Big Boned Kid Joey Slotnick Mr. Slick Paul Sado Bartender Greta Lee Kara Neimah Djourabchi Jamil Grizz Chapman Tino Kevin Breznahan Patrick Glenn Fleshler Jeffrey Danny Mastrogiorgio Brian Elena Kampouris Alexia Chris Titone Chicago Detective Douglas Taurel Thug Charles Borland Driver Fabrizio Brienza Webb Jared Sandler Cool Bar Guy (uncredited)