Best movies like The Chaperone

McCrea plays Joe Meadows, whose only ambition as a Kansas farm boy was a life at sea. He moves to New York to try to get a job as a sailor, finds it more difficult than he thought, and meets Helen Brown, who falls for him and uses her feminine wiles to try to prevent him leaving.

Set in 1870's New York, a spinster heiress is courted by a much younger, penniless man, much to the chagrin of her over-protective father, and must decide whether to spend the rest of her life alone, or marry a man who is interested in her only because of her inheritence.

Kay Kingsley, a sophisticated and successful songwriter in New York City. falls in love with a widowed rancher, Chris Heyward, she meets at the Madison Square Garden Rodeo and they get married, and leave for his ranch in the west. Her friends warn her of an early disillusionment with life on a ranch, far away from the glitter and bright lights of Broadway. Kay makes one difficulty adjustment after another, as the ranch is presided over by Chris's kids, and an incident occurs with a neighbor that prompts Kay to return to her glamorous life in New York. But she soon finds her heart is with Chris and his children.

John Bentley hates New York City, because of an unhappy romance as a young man, but his son, Ronald, tired of living in Iowa, is determined to take up residence in Manhattan. The elder Bentley therefore conspires with his New York manager, William Workman, to involve Ronald in so much trouble that he will gladly return to the sedate life of an Iowa burgher. Arriving in Manhattan, Ronald strikes up an acquaintance with Meg, a telephone operator, whose brother, Jimmy, has come under the evil influence of Jerry. Jerry and Jimmy rob a wealthy woman, and Ronald is charged with the crime on circumstantial evidence, keeping quiet in order to protect Jimmy.

A young man bets $10,000 that for 24 hour he can tell nothing but the truth.

An ironworker and his equally tough friend decide to leave New Orleans to work as beam-walkers on a New York City skyscraper. This arouses the ire of his Cajun girlfriend who promptly shoots at him as he walks away and then follows him to the Big Apple where she becomes a nightclub performer.

Set in New York City, flapper Pink Watson works a telephone operator at a cement factory who dreams of marrying rich. Her constant daydreaming of wealth annoys her fellow workers, and ruins the heart of one of her worshiping colleagues.

A self-styled "urban guerrilla" in Greenwich Village is sent on various assignments across the country by a mysterious "commander."

Lucy Honeychurch and her nervous chaperone embark on a grand tour of Italy. Alongside sweeping landscapes, Lucy encounters a suspect group of characters — socialist Mr. Emerson and his working-class son George, in particular — who both surprise and intrigue her. When piqued interest turns to potential romance, Lucy is whisked home to England, where her attention turns to Cecil Vyse. But now, with a well-developed appetite for adventure, will Lucy make the daring choice when it comes to love?

Biographical film based loosely on the life of 1920s stage star Jeanne Eagels.

Joanna Manners is a flapper with a million-dollar figure, million-dollar looks, and a million dollars in cash. She falls in love with John Wilmore, a gut who hasn't got a dime nor a pot to put it in if he had a dime. There are those who object. Especially, the crowd of gold-digging gigolos and hustlers she knows.

After young playwright, David Shayne obtains funding for his play from gangster Nick Valenti, Nick's girlfriend Olive miraculously lands the role of a psychiatrist—but not only is she a bimbo who could never pass for a psychiatrist—she's a dreadful actress. David puts up with the leading man who is a compulsive eater, the grand dame who wants her part jazzed up, and Olive's interfering hitman/bodyguard—but, eventually he must decide whether art or life is more important.

Jack's father lowers the boom when his irresponsible rich-kid ends up in jail after a night of debauchery. The father appoints Ossie, Jack's cousin, as guardian, not realizing that Ossie is just as bad. They set off on a transcontinental trip with mischief on their minds.

In 1920s New York City, a Black woman finds her world upended when her life becomes intertwined with a former childhood friend who's passing as white.

A young woman from Kansas moves to New York City, becomes highly successful at a prestigious modeling agency, and falls in love with a married man.

A fragile Kansas girl's unrequited and forbidden love for a handsome young man from the town's most powerful family drives her to heartbreak and madness.

The story of a group of friends in turn of the century New York, from their early days as street hoods to their rise in the world of organized crime...

Dixieland cornetist Red Nichols runs into opposition to his sound, but breaks through to success. He marries a warm, patient woman and even finds time to raise a family. Then tragedy strikes when their daughter contracts polio.

A woman risks losing her chance of happiness with the only man she has ever loved.

Eddie is conned into fronting a speakeasy for a local gangster who intends to frame him for the murder of a cop.

Chorus girl Peggy Lane, finds a small part in a new show for David North, a stages-truck country boy. At rehearsal, David meets Delerys Devore, the show's star, and she quickly offers him a larger part in her act. Quite taken with David, Delerys invites him to her home on the pretext that Peggy will be there; when Peggy does not show up, David leaves, infuriating his hostess. Derelys has Peggy fired the next day, and in reprisal Peggy goads her into a Carmenesque fight backstage just before the show. Derelys is unable to go on stage, and Peggy takes her place, becoming the hit of the show. Peggy and David are later married and give up show business, finding contentment living on a farm.

Vivid tale of love in Tin Pan Alley.

Based on three short stories by American writer Jack London, Burning Daylight follows the lives of three thieves, three Wall Street bankers and a Klondike millionaire, tied together by one ruthless woman

Bill Dana, a New York City playboy, can't resist the flaming flappers and red-hot mamas along the Great White Way, so he decides to head out west to his uncle's ranch in Wind River, Texas. But the gold-diggers and their relatives follow him.

Meyer Rubens and his wife, Esther, own a pressing-shop in New York's Lower East Side. Esther wants to move on up to the Upper West Side. She has a rich sister, Reba, who persuades Meyer to invest in the worthless oil stock sold by her husband. The stock proves to be not worthless and Meyer and Esther become overnight millionaires. But Reba thinks Meyer, who has no taste for high society, is holding her sister back socially, so she devises some schemes that involve catching Meyer in a compromising situation with other women, so her sister can file for a divorce.

Seduced and abandoned, with child, by a charming cad, a former New York fashion model learns to detest the male race in general until befriended by a warm-hearted artist-type who shows her that life -- and men -- ain't so bad in this early talkie drama.

Babs Comet is employed by the classified ad department of the daily paper and uses her looks and position to get a husband.

Aspiring author Prudence "Prue" Severn leaves her staid home for the wild life in New York's artistic Greenwich Village community. Her concerned family hires two thrill-seeking ex-doughboys, bow-tied Bartley "Bart" Greer and his trigger-happy buddy Lee, to look after her and, hopefully, persuade her to come home. They move into Prue's apartment building, where she lives with a sculptress pal. Although interested in Bart, Prue senses he is being paid to watch over her-- so she decides to elope with the handsome Rolf.

Joseph Greer is a wealthy businessman in New York City with all the trappings including a prim-and-proper secretary, Jenny McFarlan, who takes dictation during working hours and, at night, minus her eyeglasses, serves as his nightclub companion and mistress. Then his daughter,Beatrice, whom he has never seen, shows up and moves in with him. Beatrice is a grown-up flapper who loves jazz, pool parties, flaunting prohibition and carrying-on in general. Most of her carrying-on is with the family chauffeur and her father does not approve, says so, and fires the chauffeur. His parental-guidance technique backfires as Beatrice ups and elopes with the chauffeur. Later, the father has some problems with his business associates and loses his business and most of his fixtures and disappears. But Beatrice locates him and there is a happy reunion between father and daughter, especially since daughter has brought along Jenny to cheer him up.

Fifteen years ago, their Washington Heights neighborhood was dubbed the crack-cocaine capital of the world, but today it is transforming into one of the most vibrant, Spanish-speaking communities in the United States. While the drug dealers continue to disappear, their violent legacy still casts a shadow over the neighborhood and its residents. Junior, an ex-convict struggling to get his life back on track, is a product of this legacy. His younger brother Manny, the salutatorian of his high school class, embodies the hope of the future. On the night of his graduation party, Manny finds himself faced with an ill-fated decision that could change his life forever

Young Irish lad Tommy O'Day lives in a poor section of New York's Lower East Side, and is blessed with a beautiful singing voice. After an argument with his father, who accuses him of stealing the family's life savings, Tommy leaves home and gets a job singing in a cabaret. He is successful and soon lands the lead in a Broadway revue. On opening night, just as he is about to go on stage, he receives word that his mother, who he has not seen since he left home, is dying and wants to see him.

Biographical movie about the early 20th century broadway stars Nora Bayes and Jack Norworth.

The story of Jimmy Walker who became mayor of New York in the '20s.

Mame Walsh promised their mother on her deathbed to look after little sister Janie. But Janie helps herself to everything of her sister's, be it her clothes or her men - even the money entrusted to her by fellow employees at the store they work at. Regardless, Mame can't break her promise. So when it comes to getting Janie out of trouble, big sister comes to the rescue.

A tragic love story set against the turbulent backdrop of the 1920's Chicago jazz clubs. Georgia, a beautiful black singer catches the eye of mobster Johnny Varona. But Johnny is betrothed to the daughter of mob boss Costanza, a man you don't say no to... and live! Can Johnny and Georgia find a way to fulfill their love -and- stay alive? Or will the mob prove to be an insurmountable force.

Elinor "Swifty" Forbes and her younger sister Marjory are the carefree daughters of wealthy J. D. Forbes. Their mother shows no restraint over her daughters, so they live among the flapper set. Lester Hodges, a songwriter, is enamored of Marjory, while Garside, who runs a card room, is interested in Swifty. While gambling at Garside's place, Swifty meets Roger Corbin, who works as an engineer at her father's business. Corbin falls in love with Swifty. When Mr. Forbes protests against both his daughters' behavior, they move out. Marjory marries Hodges, but eventually leaves him and returns to her parents. Swifty, who has gambled herself into debt, agrees to marry Garside. But when the couple are together in a café, prohibition agents raid the place.

Ray Henderson joins Buddy De Sylva and Lew Brown to form a successful 1920s musical show writing team. They soon have several hits on Broadway but De Sylva's personal ambition leads to friction as the other two increasingly feel left out of things.

Two down on their luck childhood friends struggle to figure out their lives. Ray a drummer in a rock and roll band, and Owen an aspiring film maker spend most of their time working menial jobs and drinking. When Owen's fiancé Lynn breaks off their engagement he finds himself spiraling, and allows Ray to come along with him to a two bit film festival he has been invited to in Kansas. There Owen makes several attempts to patch up his relationship, while Ray scams them into a deluxe suite at the local Four Seasons hotel by posing as Wally Shawn's son (who happens to be receiving a lifetime achievement award) and generally causes a major ruckus. By the end, Owen decides to make some changes in their relationship and in his life.

In 1922, a would-be classical composer gets involved with people putting on a musical revue.

Two flappers try to get their newspaper reporter boyfriends to pay attention to them.

Benny and Flo are a husband and wife dance team, Sloane and Darrel, traveling around the country as part of a revue. The revue gets picked up and taken to New York City, to be on Broadway. However, it quickly folds, and the two are forced to look for other employment. They eventually find work in a nightclub, becoming famous.But while performing at the nightclub, Flo becomes entranced by a young, sophisticated millionaire playboy, Winston.

In 1927, a Kansas City, Missouri cornet player and his band perform nightly at a seedy speakeasy until a racketeer tries to extort them in exchange for protection.

In early 1920s New York, a young man is befriended by a neighborhood mobster. He learns the trade then decides to go straight and join the police force. It isn't long before he uses his connections to destroy the mob from within.

Show girl Jill Deverne is married to song writer Fred Deverne, and everyone is involved in the Broadway night life and endless parties. Jill is being pursued by a gangster, and she leaves her husband after he spends the night with a floozie. Jill ends up as the gangster's moll, but she soon gets tired of the lifestyle.

Joan Terry, from Kansas City, comes to New York to get a job on the stage. But until she finds an opportunity, she stays at a boarding house where other talent is also waiting. To get a better chance, the people there decide to build a talent pool, where the person with the most chances for a job gets the full support, trying to get jobs for the others there too - and Joan is chosen to do that. But this is not so easy when her fiance is trying to keep her away from the stage...

18-year-old Rosie Kaplan O'Grady was found as an abandoned baby by O'Grady, an Irish policeman, and Kaplan, a Jewish pawnbroker, and raised by them as their own. She is being courted by two men; prizefighter Terry Callahan and a rich socialite, Tommy Sinclair and has to choose between them.

A New York fur saleswoman falls for a man she meets on the subway and must decide if she wants to accept a much dreamed for work transfer to Paris, or stay and get married.

A small-town girl who goes to New York hoping to become a Broadway star falls in with a fast crowd.

A girl travelling by train to meet her boyfriend meets another young man and falls in love with him.

Steve Porter, a young American bachelor and fully intending to remain as such, inherits a fortune but must get married in order to claim it.