The Settlement (1999)

"Dying is a lousy way to make a living."

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.