Dice is tasked with getting his girlfriend's brother a wedding gift, but he gets distracted at the casino and loses $100,000, which he then desperately tries to win back.

Dice gets upset when a plaster mold of his penis goes missing from an art show. Meanwhile, after Dice accidentally dings Criss Angel's Lamborghini, the "Mindfreak" sets out to use his magic against him.

Dice tries to find work when he learns that Carmen is still receiving alimony payments and gets a meeting at the Tangiers Casino. But the meeting is for 7:30 in the morning, an impossible time to wake up for.

Milkshake uses a fake name at a steakhouse to sound "mobbed up." Meanwhile, Dice gets fired as the manager of his sons' heavy metal band and is replaced by a slick Hollywood agent.

Season 1 ends with Dice's place at the top of his crew being threatened when his old buddy Bobby the Mooch returns to town with newly acquired wealth. Dice's jealous behavior causes him to lose his best friend, so he fights to win Milkshake back.