Swaggering, womanizing Jerry and his hen-pecked buddy Pat are in a bind: their clients aren't dying fast enough! They buy insurance policies from the terminally ill, and bet on them to kick the bucket on schedule. But their luck is about to change when they meet Barbara, who has a $2million policy and 3 months to live.
| Actor | Role |
|---|---|
 John C. ReillyPat | Pat |
 William FichtnerJerry | Jerry |
 Kelly McGillisFake Barbara / Ellie | Fake Barbara / Ellie |
 David RascheDenny | Denny |
 Dan CastellanetaNeal | Neal |
| BBill BolenderShamansky | Shamansky |
 Steve TylerCostar | Costar |
 Stuart PankinInsurance Agent | Insurance Agent |
 Monica StaggsReal Barbara | Real Barbara |
 Sharon BrathwaiteReceptionist | Receptionist |
 Carol MansellBookstore Cashier | Bookstore Cashier |
| JJonathan McMurtryDr. Van Buren | Dr. Van Buren |
| JJoseph K. SteilenSupportive Friend #1 | Supportive Friend #1 |
| NNathaniel SteilenSupportive Friend #2 | Supportive Friend #2 |
| RRichard L. SchnakenbergLimo Driver | Limo Driver |
| JJeffrey T. UnterkoflerRepo Man | Repo Man |
 Carrie Jean YazelBartender / Pat's Wife | Bartender / Pat's Wife |
| LLeon MichaelsWheelchair Guy | Wheelchair Guy |
| SShane McLoughlinPat's Bratty Kid | Pat's Bratty Kid |
| HHannah McLoughlinPat's Bratty Kid | Pat's Bratty Kid |
 Stephanie BlakeCarla | Carla |