During the summer of 1987, recent college grad James Brennan (Eisenberg) takes what he thinks is a going-nowhere job at his local amusement park, only to discover it's a perfect opportunity to prepare himself for the real world. Jesse Eisenberg ... James Brennan Kelsey Ford ... Arlene Michael Zegen ... Eric Ryan McFarland ... Brad Jack Gilpin ... Mr. Brennan Wendie Malick ... Mrs. Brennan Matt Bush ... Tommy Frigo Todd Cioppa ... Velvet Touch Manager Stephen Mast ... Rich Kristen Wiig ... Paulette Bill Hader ... Bobby Martin Starr ... Joel Adam Kroloff ... Adult Contestant Kristen Stewart ... Em Lewin Kevin Breznahan ... Molly Hatchet T-Shirt Guy