Best movies like The Settlement

Dying is a lousy way to make a living.

A unique, carefully handpicked, selection of the best movies like The Settlement Starring John C. Reilly, William Fichtner, Kelly McGillis, David Rasche, and more. If you liked The Settlement then you may also like: The Van, Wet Blanket Policy, Wise Guys, Now I'll Tell, One Night in the Tropics and many more popular movies featured on this list. You can further filter the list even more or get a random selection from the list of similar movies, to make your selection even easier.

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.

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Know any good movies to watch like The Settlement 1999. With a similar plot or stoyline. Suggest it.

The Van

In a working-class quarter of Dublin, 'Bimbo' Reeves gets laid off from his job and, with his redundancy payout, buys a van and sells fish and chips with his buddy, Larry. Due to Ireland's surprising success at the 1990 FIFA World Cup, their business starts off well, but the relationship between the two friends soon becomes strained as Bimbo behaves more like a typical boss.

Wet Blanket Policy

Woody Woodpecker buys life insurance with the benifactor being Buzz Buzzard who wants to collect early.

Wise Guys

Harry Valentini and Moe Dickstein are both errand boys for the Mob. When they lose $250,000, they are set up to kill each other. But they run off to Atlantic City and comedy follows.

Now I'll Tell

A two-bit gambler somehow claws his way to the top. His love for riches is only matched by his love for his wife, but he is sometimes confused by which he loves most.

One Night in the Tropics

Jim "Lucky" Moore, an insurance salesman, comes up with a novel policy for his friend, Steve: a 'love insurance policy', that will pay out $1-million if Steve does not marry his fiancée, Cynthia. The upcoming marriage is jeopardized by Steve's ex-girlfriend, Mickey, and Cynthia's disapproving Aunt Kitty. The policy is underwritten by a nightclub owner, Roscoe, who sends two enforcers - Abbott and Costello - to ensure that the wedding occurs as planned.

Just My Luck

Norman works in a jewellers workshop and fantasises (in the nicest way) about meeting the window dresser across the road from his workshop. He wants to buy her a diamond pendant but calculates it will take him over 100 years to save up for it. He is talked into betting a pound on a six horse accumulator at the Goodwood races with a slightly shady bookmaker. When he has won on the first five races, the bookie owes him over 16,000 pounds and everyone begins to worry. Everyone's future depends on a single race ... what can be done ?

Amityville 3-D

To debunk the Amityville house's infamous reputation and take advantage of a rock-bottom asking price, skeptical journalist John Baxter buys the place and settles in to write his first novel. But as soon as the ink on the deed has dried, people who have come into contact with John and the house begin to meet with shocking fates. Is it all just coincidence, or is the house really the gateway to hell?

Beer League

An unemployed slacker inspires his softball teammates to improve their game to avoid getting kicked out of the local league.

California Split

Carefree single guy Charlie Waters rooms with two lovely prostitutes, Barbara Miller and Susan Peters, and lives to gamble. Along with his glum betting buddy, Bill Denny, Charlie sets out on a gambling streak in search of the ever-elusive big payday. While Charlie and Bill have some lucky moments, they also have to contend with serious setbacks that threaten to derail their hedonistic betting binge.

Castle Falls

Rival gangs seek out millions of dollars hidden inside a luxury condominium that's scheduled to be demolished, but first they have to deal with the demolition prep crewman who found the loot first.

Collision Course

A Japanese investigator and a Detroit cop team up to track down a stolen prototype turbocharger.

Don't Bet on Blondes

Owen, a small time bookie, decides to open an insurance business as it involves lesser risk. His first client is Colonel Youngblood who insures his daughter, Marilyn, against marriage.

Mumsy, Nanny, Sonny & Girly

A wealthy, fatherless British clan kidnaps bums and hippies and forces them to participate in an elaborate role-playing game in which they are the perfect family; those who refuse or attempt escape are ritualistically murdered.

Double Indemnity

A rich woman and a calculating insurance agent plot to kill her unsuspecting husband after he signs a double indemnity policy. Against a backdrop of distinctly Californian settings, the partners in crime plan the perfect murder to collect the insurance, which pays double if the death is accidental.

Dirty Rotten Scoundrels

Two con men try to settle their rivalry by betting on who can be the first to swindle a young American heiress out of $50,000. A loose remake of Bedtime Story (1964).

The End

Wendell Lawson has only six months to live. Not wanting to endure his last few months of life waiting for the end, he decides to take matters into his own hands and enlists the help of a delusional mental patient to help him commit suicide.

Fast Company

The temperamental Carol Maldon leaves New York behind to take control of her father's stable, she inherited. Rick Grayton is a horse racing trainer who lucked into training a champ, the horse 'Gay Fleet'. Only nobody knows 'Gay Fleet' is any good yet. Rick has been intentionally losing so that he can buy the horse with a low-ball offer to the owner Carol. However Mercedes Bellway, a rival barn and in love with Rick, figures out his plan and tells Carol.

Fool Coverage

Daffy Duck is a life-insurance-peddler, who arrives uninvited at Porky Pig's door to persuade Porky to purchase an insurance policy, on the pretext that Porky's home is loaded with hazards. When Porky rejects Daffy's claim that accidents in the home are "waiting" to happen, Daffy rigs some accidents. But each time, the calamity strikes only Daffy, who is buried in clutter from a closet and blasted in the explosions of kitchen stove gas and a dynamite stick.

Bullseye!

Spies force two British con men to pose as look-alike scientists peddling cheap-energy fusion.

Sonic the Hedgehog 3

Heroes Sonic, Tails, and Knuckles must face a mysterious new adversary, Shadow the Hedgehog, as Dr. Robotnik reemerges after his defeat with a new plan.

Hail Caesar

Caesar is having a hard time dividing his time between his band and his rich girlfriend, Buffer. Buffer's dad doesn't like Ceasar, so he makes Caesar a bet. If Caesar can make a hundred thousand dollars within six months, he can stay with Buffer... but if he fails, their relationship is over forever. How can Ceasar win the bet if he only knows how jam with his band?

Hook, Line and Sinker

Told he is terminally ill, an insurance executive goes on a credit-card spending spree--and then learns his medical diagnosis was a mistake.

Dream with the Fishes

A suicidal man who can't kill himself agrees to finance his terminally ill neighbor's bucket list of fantasies if, at the end, the neighbor will kill him.

All Hat

An ex-con returns to his rural Ontario roots and outwits a corrupt and wealthy thoroughbred owner trying to take over a slew of local farms. Ray Dokes, a charming ex-ballplayer, returns from jail to discover the rural landscape of his childhood transformed by urban development. Determined to stay out of trouble, Ray heads to the farm of his old friend Pete Culpepper, a crusty Texas cowboy who trains losing racehorses and whose debts are growing faster than his corn.

Who's Your Monkey?

In Jacksonville, Florida, four friends since grade school who are now in their early 30s face the challenges of adulthood: Hutto is about to become a father, Laith is intimidated by his girlfriend's sexuality, a grieving Bobby drinks heavily and sleeps on the grave of a girlfriend who's been dead 18 months, and Mark, an OB/GYN who loves his work, can't practice medicine because he can't afford malpractice insurance. Things come to a head when Mark needs his three friends' help after a belligerent animal-abusing pornographer attacks Mark with a gun over something Laith did. A midnight road trip tests friendship: can the guys help each other?

You Can't Buy Luck

When a gambler is accused of murder, the pretty orphanage employee he loves sets out to prove him innocent of the crime.

Hot Millions

A con artist gains employment at an insurance company in order to embezzle money by re-programming their "new" wonder computer.

Destroyer

A prison riot breaks out at the moment of a serial murderer's execution by electrocution, and his fate becomes indeterminate when the prison is shut down. 18 months later, a team of filmmakers converge on the prison to film a women-in-prison exploitation flick, but find that a certain somebody is disrupting their shooting schedule...

I'll Remember April

Four young boys find a shipwrecked Japanese sailor during World War II and struggle with the decision to save him.

The Godson

After the death of his older brother, Guiseppe "the guppy" Calzone becomes head of the Calzone Mob family. His aging father knows his son is not cut out for the job, so he sends him to "Mafia University". The head of a rival Mafia Family sees this as an opportunity to strike and bring the Calzone Family to its knees. Surrounded by danger, double-crossing and pasta.

The Prime Gig

Pendelton "Penny" Wise is a smooth-talking con-artist who makes a living by scamming people with phoney travel comp vacations over the phone when, desperate for more fast cash, he's called to work for a shady, veteran con businessman, named Kelly Grant, in selling property for a gold mine over the phone, which takes a turn when Penny begins a relationship with Grant's mistress Caitlin, where Penny throws common sense and caution to the wind to woo her, while we wonder who is scamming who here. Written by Matthew Patay

The Lemon Drop Kid

When the Lemon Drop Kid accidentally cheats gangster Moose Moran out of his track winnings, the Kid promises to repay Moose the money by Christmas. Creating a fake charity for "Apple Annie" Nellie Thursday, the Kid tricks his gang into donning Santa suits and "collecting dough for old dolls" like Nellie who have nowhere to live.

The Ties That Bind

The Ties That Bind is an experimental documentary about the filmmaker's mother, who was born and lived in southern Germany from 1920-1950. Through a mixture of personal anecdote and social history, she describes the rise of Nazism, the war years, and the Allied occupation, during which she met her future husband, an American soldier. The Ties That Bind breaks with the usual format of war documentaries, thus allowing a different portrait of the individual to emerge, while it reflects on the current political situation in America and the filmmaker's activities in relation to those issues.

Deadly Bet

Jeff Wincott plays a gambler who puts his life on the line to buy his way out of the clutches of a mobster.

ReMastered: Tricky Dick & The Man in Black

This documentary chronicles Johnny Cash's 1970 visit to the White House, where Cash's emerging liberal ideals clashed with Richard Nixon's policies.

Before I Kick the Bucket

In this heart-warming and ultimately life-enhancing documentary, the extraordinary Rowena Kincaid, a terminally ill young woman with a wicked sense of humor, takes on a wild bucket list. - - - What would you do if you only had months to live?

The Duchess and the Dirtwater Fox

A female hustler is chasing after rich men, but becomes repeatedly mixed up with a suave con man and card shark through a series of misadventures before falling in love with him.

Funeral Kings

It's always a good day for a funeral at St. Mark's Middle School. Andy and Charlie, two altar servers, don't just get to miss class anytime a parishioner kicks the bucket, they cut out early and play hooky as soon as the service is over. Eventually their irreverent personalities will put them in a situation that is too big for them to handle.

A Kiss in the Dark

Eric Phillips's manager buys him a building with tenants, one of whom catches his eye.

The Bride Walks Out

Carolyn Martin is a fashion model who hastily marries her boyfriend, engineer Michael Martin. But part of the marriage arrangement requires that Carolyn quit her $50-per-week modeling job to be a full-time housewife; the couple will instead live on Michael’s $35-per-week job.

How to Go Out on a Date in Queens

A self-proclaimed dating expert tries to get his best friend, who lost his wife two years earlier, back into the dating scene, with disastrous results.

Lady Bodyguard

A.C.Baker, advertising executive for an insurance company, approaches test pilot Terry Moore with a proposition that in return for using his picture and endorsement he will get a paid-for-a-year $1000 policy. High-risk Terry agrees. George MacAlister fires his secretary, Miss Tracy, just as she is typing up the policy and she, for spite, changes the amount from a thousand dollars to one million dollars. A.C. delivers the policy, without noticing the difference, to Terry at a party at the Frolics Club, a cheap joint wedged between a burlesque house and a flop house hotel. Three characters, an elderly hat-check "girl" known as Mother Hodges; Avery Jamieson, a broken-down actor; and bartender Harry Gargan are named beneficiaries. When the company discovers the error, A.C. is sent to get back the policy and, pending that, don't let Terry make any test flights.

Home and Away

When George discovers that he has won the pools, there is huge excitement in the household. But it turns out that it's his son who has won, in partnership with the son of a woman against whom George has some ill feelings.

I'll Be Seeing You

A woman finds out she has a half sister when he father disappears and her half sister turns up dead.

Rooster

A physically small police psychologist and a physically large insurance detective team up on an arson case.

The Science Of Fasting

While life expectancy is increasing in Western countries, cases of diabetes, hypertension, obesity and cancer are increasing, and the use of medication has exploded. Does this mean that in order to live to a ripe age we are condemned to swallow more and more drugs? What if there was another way? For half a century, in Russia, Germany and the U.S., doctors and biologists have been exploring a different therapeutic approach: fasting. The results are amazing. Soviet researchers have provided a body of clinical studies of exceptional health…only published in Russian, and thus unknown in the West. Young biologists from the University of Los Angeles have overturned conventional wisdom and used molecular biology to demonstrate the powerful effects of fasting. This research suggests a wide-ranging potential, which could include treatments for the disease of the century, cancer. If these scientists are right, maybe our approach to disease and treatment will need a rethink.

Alias Jimmy Valentine

An Incompetent insurance salesman sells a policy to Jesse James and has to protect his client until he can get it back.

Once & Future Queen

This film follows the life of a mentally ill street itinerant whose name is not worthy of mention. When not sleeping in the gutters of Manhattan's Lower East Side, our protagonist keeps busy juggling her schedule of drug abuse, trips to her shrink, and stealing from those misguided souls who, after taking pity on her, allow her temporary shelter in their homes.

Seventy Deadly Pills

A small boy, Dickie Goodwin, finds some strychnine pills mixed with sweets in a stolen car left in a deserted garage. With them he buys his way into the Rocket Gang. Brian, the leader, shares out the pills for swaps next day. One of the gang eats hers and collapses. The police frantically search for the pills and a broadcast appeal is made. Brian hears this and reaches the gang at Battersea funfair just in time to save them.

The Confidence Man

Policeman Stevie Grimes never lost his trust in the police force but has been suspended a few months for accidentally shooting and killing a young boy. Because of lack of evidence in court and with some help from his former partner, Stevie soon finds himself working as a policeman again. When Stevie returns to the police force he is bound to a desk job. Stevie misses the action of the streets and asks his former partner who has been promoted to lieutenant, if there are any interesting assignments available, the lieutenant knows just a case that Stevie can work out perfectly. The lieutenant and Stevie do however share a dark secret... It wasn't Stevie that shot the young boy but somebody very important within the police force, Stevie took the fall out of loyalty.

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