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Scott, fresh off being dumped by his girlfriend, helps prevent his brother Joey from being killed by money-lenders by reluctantly agreeing to an offer to assist the terminally ill man across the hall with his suicide. Scott employs his friend Cozzo to help build the machine that will do it. But Cozzo, whose prying wife Debbie is a police officer, decides that if he's going to take the risk, they should turn assisted-suicide into a business.

When the guys' second client deems their assisted-suicide operation amateurish, Scott drags his bumbling group to a business seminar, where things get even more unprofessional. Joey, meanwhile, still owes money to his lender and, as punishment, has to sadistically punish someone else.

Scott dances on the edge when he falls for Julia, his first client's beautiful daughter, but has to keep her from discovering his assisted-suicide business. Meanwhile, Cozzo's wife, Debbie, becomes suspicious after finding Cozzo's large wad of money. And the guys make a dirty old man's final wish come true.

When Scott's troubles in the bedroom are exacerabated by his sexual harassment at work, he plans a special night for Julia. Joey falls off the gambling wagon and Cozzo has to pretend he's Jewish in order to satisfy a client's dying needs.

Scott and Cozzo force Joey to go to a gambling addicts group, only to have it backfire on their business. Cozzo decides to get healthy for his baby. Scott, in a desperate move to get Julia back, claims he's struggling with an addiction of his own - sex.

After Julia breaks up with Scott, he decides to get away and suggests the guys splurge on a corporate retreat at a beautiful hotel in the country. While there, Cozzo faces his body issues, Scott hooks up with his ex-girlfriend and Joey meets his childhood hero, an 80s TV star who asks Joey to help him die.