Matt goes to work every day to find himself taunted by fellow employees. In need of a fresh start, Matt leaves Atlanta and returns to his roots in Scarsdale, New York. Matt soon links up with his eccentric childhood friends and notices that the old town is now shot to hell. Matt and his gang take on an array of perplexing ordeals to redeem the town along with his grandfather's cheese shop. Will Matt and the boys win the town back like real Ivy leaguers or will they live up to being "Big Losers"?
| Actor | Role |
|---|---|
 Rob GleesonMatthew Klein | Matthew Klein |
 Dane DavenportJames | James |
 David CarzellRob | Rob |
 Karlee EldridgeSarah | Sarah |
| JJohnson CooleyBrick | Brick |
| NNadia ZebibJen | Jen |
 Thomas Mikal FordJamaican Hard Worker | Jamaican Hard Worker |
 Todd Anthony ManaigoActor | Actor |
| KKathleen SeconderWaitress | Waitress |
 Ari BlinderAgent David Reed | Agent David Reed |