The Settlement_
"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.
Starring
John C. Reilly, William Fichtner, Kelly McGillis
Updated Feb 16, 2026
WHERE TO WATCH
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Year context
The Settlement was released 27 years ago in 1999.
Overview
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 termina...
The Settlement is a Comedy, Drama film with a runtime of 1h 41m.
CAST (15)
John C. Reilly
Pat
William Fichtner
Jerry
Kelly McGillis
Fake Barbara / Ellie
David Rasche
Denny
Dan Castellaneta
Neal
Bill Bolender
Shamansky
Steve Tyler
Costar
Stuart Pankin
Insurance Agent
Monica Staggs
Real Barbara
Sharon Brathwaite
Receptionist
Carol Mansell
Bookstore Cashier
JM
Jonathan McMurtry
Dr. Van Buren
JK
Joseph K. Steilen
Supportive Friend #1
NS
Nathaniel Steilen
Supportive Friend #2
RL
Richard L. Schnakenberg
Limo Driver
DETAILS
FREQUENTLY ASKED QUESTIONS
What is The Settlement about?
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.
How long is The Settlement?
The Settlement has a runtime of 101 minutes (1h 41m).
Who stars in The Settlement?
The cast of The Settlement includes John C. Reilly, William Fichtner, Kelly McGillis, David Rasche, Dan Castellaneta.
What is the rating of The Settlement?
The Settlement has a rating of 5.3 out of 10 based on 3 votes on TMDB.
GENRES (2)
Comedy
Drama
