Best movies like The Rest of Your Life

A unique, carefully handpicked, selection of the best movies like The Rest of Your Life Starring Christopher Wieland, Eric Siensa, Brian Sharpe, Beth Lacke, and more. If you liked The Rest of Your Life then you may also like: We'll Never Have Paris, Whiteboyz, Only the Lonely, The Racket, A Jazzman's Blues 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.

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We'll Never Have Paris

Quinn, a neurotic man, is diagnosed with a harmless eye condition and soon after his life spirals out of control. He second-guesses his plans to propose to his longtime girlfriend, Devon, after his beautiful coworker, Kelsey, confesses that she has a crush on him. After a conversation with his best friend, Jameson, he clumsily tries to explain his doubts to Devon, but his possible proposal turns into a break-up. When Devon flees to Paris, he follows her in a last-ditch effort to win back "the one."

Whiteboyz

In a virtually all-white Iowa town, Flip daydreams of being a hip-hop star, hanging with Snoop Doggy Dogg and Dr. Dre. He practices in front of a mirror and with his two pals, James and Trevor. He talks Black slang, he dresses Black. He's also a wannabe pusher, selling flour as cocaine. And while he talks about "keeping it real," he hardly notices real life around him: his father's been laid off, his mother uses Food Stamps, his girlfriend is pregnant, James may be psychotic, one of his friends (one of the town's few Black kids) is preparing for college, and, on a trip to Chicago to try to buy drugs, the cops shoot real bullets. What will it take for Flip to get real?

Only the Lonely

Danny Muldoon, a Chicago policeman, still lives with his overbearing mother Rose. He meets and falls in love with Theresa Luna , whose father owns the local funeral parlour. Naturally, his mother objects to the relationship, and Danny and Theresa must either overcome her objections or give up the romance.

The Racket

A renegade police captain sets out to catch a sadistic mob boss.

A Jazzman's Blues

A tale of forbidden love and family drama unravels 40 years of secrets and lies against a soundtrack of juke joint blues in the Deep South.

Kissing a Fool

An egotistical television personality enlists the assistance of his best friend in putting the fidelity of his fiancé to the test in this amiable comedy of the sexes. Told in flashback, the film takes a familiar love-triangle scenario and gives it a bitter twist. With a bride who seems too good for either suitor, the film is sustained by one question - who will she choose?

City That Never Sleeps

Chicago cop Johnny Kelly, dissatisfied with his job and marriage, would like to run away with his stripper girlfriend Angel Face, but keeps getting cold feet. During one crowded night, Angel Face decides she's had enough vacillation, and crooked lawyer Biddel has an illegal mission for Johnny that could put him in a financial position to act. But other, conflicting schemes are also in progress...

A Night in the Life of Jimmy Reardon

A recent high school graduate is faced with two options, either go to a business school where his father wants him to go to, or get a full time job. However he decides to defy his father and go to Hawaii. Trouble is he has no money. Along the way he comes to understand his parents and eventually bonds with his father.

Cowboy

Chicago hotel clerk Frank Harris dreams of life as a cowboy, and he gets his chance when, jilted by the father of the woman he loves, he joins Tom Reece and his cattle-driving outfit. Soon, though, the tenderfoot finds out life on the range is neither what he expected nor what he's been looking for...

Prime Cut

A group of ruthless Chicago mob enforcers are sent to Kansas City to settle things with the owner of a slaughterhouse who has taken money that is not his to keep.

The Dilemma

Longtime friends Ronny and Nick are partners in an auto-design firm. They are hard at work on a presentation for a dream project that would really launch their company. Then Ronny spots Nick's wife out with another man, and in the process of investigating the possible affair, he learns that Nick has a few secrets of his own. As the presentation nears, Ronny agonizes over what might happen if the truth gets out.

The Exile

An idealistic young man is torn between a sultry Chicago nightclub owner and a Scottish South Dakotan farmgirl.

Gladiator

Tommy Riley has moved with his dad to Chicago from a 'nice place'. He keeps to himself, goes to school. However, after a street fight he is noticed and quickly falls into the world of illegal underground boxing - where punches can kill.

Southside with You

Chronicles a single day in the summer of 1989 when the future president of the United States, Barack Obama, wooed his future First Lady on an epic first date across Chicago's South Side.

She's the One

Mickey, a free-spirited New York cabbie, and Francis, a materialistic Wall Street stockbroker, are extremely competitive and confused about women as a result of their father's influence. Though they disagree about everything, they have one thing in common: Mickey's ex-fiance Heather is Francis's secret love. Though both brothers have beautiful wives, Heather triggers their longtime sibling rivalry

The World Changes

Generational saga tracing the events in the lives of the midwest pioneering Nordholm family, as seen through the eyes of businessman Orin Nordholm Jr., who ages from a youth to an elderly grandfather.

This Love of Ours

At a convention, medical researcher Michel Touzac goes with colleagues to see stage caricaturist Targel, whose assistant Florence recognizes him...and attempts suicide. Saved by Touzac's new technique, Florence is revealed in a flashback as Michel's abandoned wife Karin, whom their daughter Susette thinks is dead. Can Susette cope if they now re-unite?

Call Jane

A married woman with an unwanted pregnancy lives in a time in America where she can't get a legal abortion and works with a group of suburban women to find help.

Chicago Deadline

On Chicago's South Side reporter Ed Ames finds the body of a dead girl. Her address book leads to a host of names of men frightened by her death but claiming never to have known her. Ames comes to know quite a lot, dangerously so.

A Holiday for Love

A man is sent to a small town to assess which of the workers in the local factory that supplies the town with jobs should get the boot when the downsizing begins. He gets sidetracked when he falls in love with a local, a cute single mom.

Gangster Land

The story of America's most famous mobsters and their rise to power. Examine Al Capone's ascension through the eyes of his second in command, “Machine Gun” Jack McGurn.

Desperately Seeking Seka

Desperately Seeking Seka is an adventurous odyssey through X-rated America, featuring open-hearted interviews with some of the most well known people in adult entertainment of yesteryear and today.

Love Strikes Twice

Maggie and Josh are an out-of-sync married couple. Maggie wishes for a do-over and wakes up 15 years earlier. Will she choose Josh again or is an ex-boyfriend her happily ever after?

One Small Hitch

On a flight home to Chicago for a family wedding, childhood friends Josh and Molly innocently agree to fake a wedding engagement to make Josh's dying father happy. Things quickly get out of hand with their two boisterous families, and a series of events causes them to pretend to be a couple and start planning a phony wedding. When the playacting begins to foster real feelings, the two must make some serious decisions: Split up and return to their lives in LA, or make a life as a couple back in Chicago?

When Sparks Fly

A big city journalist is sent back to her small hometown to write a Fourth of July story and discovers the life and love she left behind are exactly what she's been missing.

Marry Me in Yosemite

Zoe is a top photojournalist who has published successful coffee table books featuring her images of iconic places. Her publisher wants her next subject to be Yosemite, so she heads west despite not being sure she can do justice to the majesty of the landscape. While there, she meets Jack, an intriguing tour guide who opens her eyes to new possibilities as they take a journey together.

Blending Christmas

The holiday season is in full swing when Emma learns that the resort where she used to spend Christmases with her family is being redeveloped.

We Grown Now

Two young boys, best friends Malik and Eric, discover the joys and hardships of growing up in the sprawling Cabrini-Green public housing complex in 1992 Chicago.

The Perfect Christmas Present

Tom Jacobs is Mr Christmas! He's built an entire business around helping clients find the perfect gift. But what happens when he falls for one lucky recipient?

Love at the Thanksgiving Day Parade

As Chicago gears up for its annual Thanksgiving Day parade, Emily Jones, an eager parade coordinator is shocked when Henry Williams, a wealthy new development consultant, is brought in to analyze the parade's finances.

Cold Justice

When a washed-up boxer invites a British priest to minister in his South Chicago neighborhood, he never suspects that the priest is not who he says he is.

Love on Safari

An American web designer inherits an animal reserve in South Africa. A no-nonsense ranger takes her on a safari in hopes that she will fall in love with the land, the animals and him.

Love in the Sun

When successful dating app creator Alana hesitantly gets engaged, she returns to her hometown in Florida to deliver the news to her dad. Upon returning home, she crosses paths with her former flame, Kai, and finds herself falling in love with the fun and adventurous lifestyle tied to her community. As Alana and Kai work together to help her dad restore his declining property, Alana finds herself conflicted as to whether or not her current way of living makes her happier than the home and community that she always knew and loved.

The Wedding Ring

Kate Sterling’s entire life is about proposals. As a jewelry designer she’s created rings for more happy couples than she can count, however none for herself yet. At her sister’s marriage, Kate is given a second change to connect with her childhood sweetheart. Now she has to decide whether their feelings have changed, or if the wedding will re-kindle the sparks that once united them; giving Kate the ring she’s been waiting for her whole life!

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