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Movies like The Pick-up Artist

Key Features:
Womanizer, Romantic comedy, Gambling addiction, Charming protagonist, Redemption, Love conquers all, Family conflict, New York City, Self-improvement, Relationship dynamics
Tone:
humorous, earnest
Target Audience:
Romantic comedy fans, Relationship drama viewers, Lighthearted entertainment seekers
Emotional Arc:
Infatuation → Conflict → Resolution

The Pick-up Artist

1987-09-18
The Pick-up Artist Poster - Find Similar Movies

A womanizer meets his match when he falls for the daughter of a gambling addict who is in debt to the mob.

Genres
Romance, Comedy, Crime
Cast
Molly Ringwald, Robert Downey Jr., Dennis Hopper, Danny Aiello, Harvey Keitel, Vanessa Williams, Mildred Dunnock, Brian Hamill, Tamara Bruno, Angie Kempf
Crew
James Toback, James Toback
Rating
5.6(197 votes)
The Pick-up ArtistThe Pick-up Artist
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Love Addict
5.9

Gabriel can't resist a beautiful woman. But his womanizing attitude is taking a toll on his career and social life. He decides to hire a life coach to help him.



The Gambler
6.7

New York City English professor Axel Freed outwardly seems like an upstanding citizen. But privately Freed is in the clutches of a severe gambling addiction that threatens to destroy him.



Falling Up
5.291

A nursing student forced to quit school for family reasons winds up taking a job as a doorman in an elite apartment building in New York City, where he sparks to one of his residents.



Arthur
Arthur(2011)
5.6

A drunken playboy stands to lose a wealthy inheritance when he falls for a woman that his family doesn't like.



Goodrich
Goodrich(2024)
6.315

Andy Goodrich's life is upended when his wife enters a rehab program, leaving him on his own with their young kids. Goodrich leans on his daughter from his first marriage, Grace, as he ultimately evolves into the father Grace never had.



Heartbreakers
6.1

Max and Page are a brilliant mother/daughter con team who have their grift down to a fine science. Max targets wealthy, willing men and marries them. Page then seduces them, and Max catches her husband in the act. Then it's off to palimony city and the next easy mark.



10 Rules for Falling in Love

Womanizer father teaches clumsy son the decalogue of seduction: ten foolproof rules to make any woman fall in love. But the results will be not what expected.



Players
Players(2024)
6.082

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.



Betting on the Bride

A womanizer bets that he can get someone to accept his marriage proposal after dating them for just 30 days. What he doesn't know is that the woman he targeted has some serious commitment issues.



Frankie and Johnny
6.8

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, he develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.



Trust the Man
5.1

Overachieving actress Rebecca must come to grips with her failing marriage to stay-at-home dad Tom. While Rebecca's slacker brother Tobey can't seem to commit to his aspiring-novelist girlfriend, Elaine. As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.



Mickey Blue Eyes
5.7

An English auctioneer proposes to the daughter of a mafia kingpin, only to realize that certain "favors" would be asked of him.



The Rebound
6.498

Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny, and it isn't long until Aram and Sandy find out they get along wonderfully and start to date. But is their relationship real or is it, in fact, just a rebound for both of them?



Win It All
5.674

A gambling addict faces a conflict when entrusted with keeping a bunch of money that isn't his.



Yes Man
Yes Man(2008)
6.7

Carl Allen, a guy whose life is going nowhere, signs up for a self-help program based on one simple covenant: say yes to everything…and anything.



Easy Money
6

To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him.



Focus
Focus(2015)
6.9

Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.



Alfie
Alfie(2004)
5.842

A tale of a philosophical womanizer who is forced to question his seemingly carefree existence.



The Country Girl
6.901

An actor on the skids is given one more chance to regain his stardom, as well as his self-respect, yet his alcoholism may prevent that from happening.



Roger Dodger
6.108

A smooth-talking ad executive attributes his remarkable success with women to his ability to manipulate their emotions from the moment he first meets them. When his teenage nephew drops in for a visit, he soon learns that his approach isn't as foolproof as he thought when he attempts to teach the boy how to pick up women.



The Hustle
6.189

Two female scam artists, one low rent and the other high class, compete to swindle a naïve tech prodigy out of his fortune. A remake of the 1988 comedy "Dirty Rotten Scoundrels."



Fingers
Fingers(1978)
6.3

A wanna-be concert pianist spends his days making a living by collecting debts for his Mafioso father, a lifestyle that could eventually ruin his dreams of a musical career.



Once Around
6

Renata Bella feels like a failure at life and career. But when Renata attends a seminar on selling real estate, she finally finds True Love. Sam Sharpe, while a top-notch, successful salesman, is much older than Renata. She is swept away by his excessively flamboyant style and irrepressible nature. The very traits she finds romantic, however, lead to repeated conflict with her family, especially her beloved father Joe, leaving Renata trapped in the middle.



Group Sex
Group Sex(2010)
5.75

Herman has a weakness for strip clubs. Donny has a thing for condiments and Tiffany is a newly celibate martial artist. These are Andy's new friends after he unsuspectingly follows his dream girl into a sexual addiction recovery group. At first this seems like the best possible news! However, Andy's professional and personal life begins to unravel as he deepens his ties to this lovable, but damaged group.



Picking Up the Pieces
4.223

A small New Mexican village discovers a severed hand that is considered a miracle of God, when it actually belongs to a murdered spouse with a husband in search of it.



American Loser
5.186

A dramatic comedy about a self-induced attention-deficit disordered, learning disabled, Tourette's syndrome suffering, balance impaired, ex-alcoholic young man from the Upper East Side of Manhattan and the gold-digging girl who inspires him to try to get it together.



Two Girls and a Guy
5.245

Two women confront their boyfriend, a two-timing actor who professed eternal love to each.



Lucky You
Lucky You(2007)
5.6

A professional poker player whose astounding luck at the table fails to translate into his lonesome love life attempts to win the World Series of Poker while simultaneously earning the affections of a beautiful Las Vegas singer.



The Escort
5.968

Desperate for a good story, a sex-addicted journalist throws himself into the world of high-class escorts when he starts following a Stanford-educated prostitute.



Why Him?
Why Him?(2016)
6.379

A dad forms a bitter rivalry with his daughter's young rich boyfriend.



The Debt Collector
5.789

A classically-trained martial artist goes to work as a debt collector for the mob. The job seems easy enough, until one “client” pulls him into a situation deeper than could ever be expected.



The Bounce Back
6.4

Father, author and relationship expert, Matthew Taylor is on a whirlwind book tour promoting his new best seller, The Bounce Back. He's got it all figured out until he meets the acerbic Kristin Peralta, a talk show circuit therapist who's convinced he's nothing but a charlatan. Matthew's life is turned upside down when he inadvertently falls for Kristin and has to face painful truth of his past relationship.



Loosies
Loosies(2012)
5.683

A young pickpocket in the New York subways, living a fast, free, lifestyle is confronted by a woman whom he had a one night affair with, she informs him that she is now pregnant with his child, he must now choose between continuing the lifestyle he lead or take responsibility for his actions.



Rhinestone
4.8

After a big-time country singer brags that she can turn anybody in to a country-singin' star, she's out to prove she can live up to her talk when she recruits a cab-driver as a country singer. He's scheduled to sing at a big-time NYC country night club and she puts her ample powers to work in preparing her protege.



Life with Mikey
5.7

Michael Chapman, a former child TV star, runs a struggling talent agency specilizing in child acts. When a young girl off the street puts on a real performance after he catches her picking his pocket, he may have just found the next big thing.



How to Break Up with Your Douchebag

This comedy takes its cue from such female-centered films as "Bridesmaids" and "Trainwreck." Pic centers on a woman who makes a living from breaking up couples and decides to take on the task of splitting up her sister's relationship with her jerk of a boyfriend.



Set It Up
Set It Up(2018)
6.92

Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.



On the Rocks
6.1

Faced with sudden doubts about her marriage, a young New York mother teams up with her larger-than-life playboy father to tail her husband.



Mo' Money
Mo' Money(1992)
5.528

Trying to get his act together, a con artist gets a job in a credit card company. He falls in love with a fellow employee, he steals a couple of cards, everything is going great. But soon, the chief of security drags him into the big leagues of criminals...



The Life Coach
5.4

Max Chêne is a life coach who helps to motivate everybody from professional athletes to government ministers to business executives. After his gambling debts get out of control and his wife throws him out, he is approached to take on a unique client.



Tootsie
Tootsie(1982)
7.2

When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego – Dorothy Michaels – in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.



Barfly
Barfly(1987)
6.9

Downtrodden writer Henry and distressed goddess Wanda aren't exactly husband and wife: they're wedded to their bar stools. But, they like each other's company—and Barfly captures their giddy, gin-soaked attempts to make a go of life on the skids.



52 Pick-Up
5.9

Harry Mitchell is a successful Los Angeles manufacturer whose wife is running for city council. His life is turned upside down when three blackmailers confront him with a videotape of him with his young mistress and demand $100,000. Fearing that the story will hurt his wife's political campaign if he goes to the police, Harry pretends that he will pay the men, but does not follow through.



Romance & Cigarettes
5.931

Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.



Uncut Gems
7.151

A charismatic New York City jeweler always on the lookout for the next big score makes a series of high-stakes bets that could lead to the windfall of a lifetime. Howard must perform a precarious high-wire act, balancing business, family, and encroaching adversaries on all sides in his relentless pursuit of the ultimate win.



Living Out Loud
5.843

Judith Moore is suddenly single after discovering her husband of fifteen years, a successful doctor, has been having an affair with a younger woman. Judith stews, plans, plots and fantasizes, but she can't decide what to do with her life until she goes out to a night club to see singer Liz Bailey, who is full of advice on life and love. While out on the town, Judith is suddenly kissed by a total stranger, which opens her eyes to new possibilities... which is when she notices Pat, the elevator operator in her building.



One for the Money
5.5

An unemployed lingerie buyer convinces her bail bondsman cousin to give her a shot as a bounty hunter. Her first assignment is to track down a former cop on the run for murder – the same man who broke her heart years before. With the help of some friends and the best bounty hunter in the business, she slowly learns what it takes to be a true bounty hunter.



Atlantic City
6.8

In a corrupt city, a small-time gangster and the estranged wife of a pot dealer find themselves thrown together in an escapade of love, money, drugs and danger.



His Kind of Woman
6.6

Career gambler Dan Milner agrees to a $50,000 deal to leave the USA for Mexico, only to find himself entangled with fellow guests at a luxurious resort and suspecting that the man who hired him may be the deported crime boss Nick Ferraro aiming to re-enter to the USA.



Matchstick Men
7.005

A phobic con artist and his protege are on the verge of pulling off a lucrative swindle when the con artist's teenage daughter arrives unexpectedly.



The Good Guy
5.503

Ambitious young Manhattanite and urban conservationist Beth wants it all: a good job, good friends, and a good guy to share the city with. Of course that last one is often the trickiest of all. Beth falls hard for Tommy, a sexy, young Wall Street hot-shot. But just as everything seems to be falling into place, complications arise in the form of Tommy's sensitive and handsome co-worker Daniel. Beth soon learns that the game of love in the big city is a lot like Wall Street -- high risk, high reward and everybody has an angle.



Gigli
Gigli(2003)
4.1

Gigli is ordered to kidnap the psychologically challenged younger brother of a powerful federal prosecutor. When plans go awry, Gigli's boss sends in Ricki, a gorgeous free-spirited female gangster who has her own set of orders to assist with the kidnapping. But Gigli begins falling for the decidedly unavailable Ricki, which could be a hazard to his occupation.



Tomcats
Tomcats(2001)
5.123

College buddies chip in and promise that the group's last unmarried man will collect a cash pot. Seven years later, the kitty is worth $500,000 -- money Michael needs to pay a gambling debt. Problem is, the only other single guy is a hopeless womanizer!



How to Be Single
6.257

New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.



Just My Luck
6.166

Manhattanite Ashley is known to many as the luckiest woman around. After a chance encounter with a down-and-out young man, however, she realizes that she's swapped her fortune for his.



Materialists
6.497

A young, ambitious New York City matchmaker finds herself torn between the perfect match and her imperfect ex.



Casanova
Casanova(2005)
6.4

With a reputation for seducing members of the opposite sex, regardless of their marital status, a notorious womanizer discovers a beauty who seems impervious to his charms. However, as he continues to pursue the indifferent lady, he finds himself falling in love.



Arthur
Arthur(1981)
6.5

Arthur is a 30-year-old child who will inherit $750 million if he complies with his family's demands and marries the woman of their choosing.



Same Kind of Different as Me

International art dealer Ron Hall must befriend a dangerous homeless man in order to save his struggling marriage to his wife, a woman whose dreams will lead all three of them on the journey of their lives.



Choke
Choke(2008)
6.1

A sex-addicted con-man pays for his mother's hospital bills by playing on the sympathies of those who rescue him from choking to death.



Trainwreck
5.799

Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.



The Gambler
6.015

Literature professor Jim Bennett leads a secret life as a high-stakes gambler. Always a risk-taker, Bennett bets it all when he borrows from a gangster and offers his own life as collateral. Staying one step ahead, he pits his creditor against the operator of an illicit gambling ring while garnering the attention of Frank, a paternalistic loan shark. As his relationship with a student deepens, Bennett must risk everything for a second chance.



Balancing Act
6.682

Giulio suddenly finds himself having to change his life when his wife, after discovering his betrayal, asks for a separation and, suddenly, the reality around him is no longer the same. Forty years old and father of two children, Giulio is forced by circumstances to say goodbye to family and economic well-being and to study new solutions in order to stay afloat and not drown in a new poverty made of double rents and double bills to pay, solitary lunches in fourth-rate restaurants, children's wishes not to be ignored and creditors to hide from.



Stand Up Guys
6

After serving 28 years in prison for accidentally killing the son of a crime boss, newly paroled gangster Val reunites with his former partners in crime, Doc and Hirsch, for a night on the town. As the three men revisit old haunts, reflect on their glory days and try to make up for lost time, one wrestles with a terrible quandary: Doc has orders to kill Val, and time is running out for him to figure out a way out of his dilemma.



She's Out of My League

When he starts dating drop-dead gorgeous Molly, insecure airport security agent Kirk can't believe it. As his friends and family share their doubts about the relationship lasting, Kirk does everything he can to avoid losing Molly forever.



Housesitter
6.1

Con artist Gwen moves into Newton's empty home without his knowledge and begins setting up house, posing as his new wife.



Crazy, Stupid, Love.

Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.



The Beautician and the Beast

A New York City beautician is mistakenly hired as the school teacher for the children of the president of a small Eastern European country.



Demolition
6.8

An emotionally desperate investment banker finds hope through a woman he meets.



She's Out of Control

A Los Angeles radio-station manager's girlfriend shows his teenage daughter how to be sexy.



Addicted to Love
6.2

Good-natured astronomer Sam is devastated when the love of his life leaves him for a suave Frenchman. He therefore does what every other normal dumpee would do — go to New York and set up home in the abandoned building opposite his ex-girlfriend's apartment, wait until she decides to leave her current lover, and then win her back.



Heist
Heist(2015)
6.142

A father is without the means to pay for his daughter's medical treatment. As a last resort, he partners with a greedy co-worker to rob a casino. When things go awry they're forced to hijack a city bus.



The Knack... and How to Get It

A nebbish schoolteacher begs his smooth (and misogynistic) pal to teach him 'the knack' – how to score with women. Serendipitously, the men meet up with a new girl in town, as well as a friendly lunatic who can’t help but paint things white.



Falling in Love
6.7

During shopping for Christmas, Frank and Molly run into each other. This fleeting short moment will start to change their lives, when they recognize each other months later in the train home and have a good time together. Although both are married and Frank has two little kids, they meet more and more often, their friendship becoming the most precious thing in their lives.



Man in Love
7.014

A debt collector strikes a deal with a debt-ridden woman struggling to care for her ailing father: he will take care of her bills if she agrees to date him.



Pocketful of Miracles

A New York gangster and his girlfriend attempt to turn street beggar Apple Annie into a society lady when the peddler learns her daughter is marrying royalty.



Sex, Love & Therapy

Lambert, a recovering sex addict, tries to redeem himself by becoming a marriage counsellor. He stays abstinent for several months, but his alluring assistant's unbridled sexuality tests his resolve.



Results
Results(2015)
5.048

Two mismatched personal trainers' lives are upended by the actions of a new, wealthy client.



The Love Punch
5.997

Retirement at last! Middle-aged and divorced, company owner Richard Jones is looking forward to a worry-free existence as he arrives at his office on his last day of work. Much to his dismay, he discovers that the management buyout of his company was fraudulent. The company is now bankrupt and the employee pension fund — including his own — has been embezzled. Enlisting the help of his ex-wife Kate, Richard sets out to track down the shady businessman behind the fraud.



All Fired Up
5.9

Victor Valance, an absent father and gambler, works with shady casino operations abroad. When he returns to Paris in need of money, he plans to take advantage that Pauline, his eldest daughter now fully responsible for the whole family, has begun to work for the Ministry of Finance. Pauline thwarts his new projects but when she realizes gangsters are looking for Victor she will put her life at risk to help him and save their family.



Murphy's Romance
6.1

Emma, a divorced single mother seeking to start her life over, moves to a small town in Arizona. She befriends Murphy, the older local pharmacist, but things turn complicated when her ex-husband shows up.



The Art of Seduction

A man and woman have great success in all of their dating pursuits. The woman uses her dating rules and fakes a car accident to capture the guy's attention, but she can't get him to succumb to her charm.



Senza nessuna pietà

Mimmo is a construction worker who only wants to live in peace, but has to work as a debt collector for his uncle. Everything changes when he meets Tanya, a beautiful, street-smart girl who shares his dream.



Spread
Spread(2009)
5.5

A gigolo must contend with the prospect that he has found true love.



Pawn
Pawn(2020)
8.433

A debt collector who looks intimidating, but actually has a warm heart, ends up becoming the guardian of a child, who has been left behind as collateral by her illegal immigrant mother.



The Meyerowitz Stories (New and Selected)

An estranged family gathers together in New York for an event celebrating the artistic work of their father.



The Girl Can't Help It

A down-and-out gangster hires a down-on-his-luck agent to make his girlfriend a recording star within six weeks.



The Love Scam
6.386

Drowning in debt, two brothers concoct a plan to scam a wealthy heiress and save their home in Naples — but unexpected love soon complicates the scheme.



Switch
Switch(1991)
5.9

Steve Brooks, a sexist womanizer, is killed by a group of his angry former lovers. In heaven, he makes a bargain with God for redemption and agrees to return to Earth. Once there, he must have a sincere relationship with a female and make her fall in love with him. If not, Steve's soul will become the property of the devil. But the devil hedges his bet, and Steve is reincarnated as a woman named Amanda Brooks.



The Con Artists
7.024

Belle Duke, in order to get revenge on her former lover Philip Bang, organize his jail break. But instead of Philip is the Italian Felice Brianza, AKAS Felix, to escape. Now Felix is obliged to help Philip to escape. He will succeeded and from that moment on the two will join to defraud Belle. The swindle plot become more complicate when Felix falls in love for Philip's daughter.



Jersey Girl
6.2

Ollie Trinke is a young, suave music publicist who seems to have it all, with a new wife and a baby on the way. But life deals him a bum hand when he's suddenly faced with single fatherhood, a defunct career and having to move in with his father. To bounce back, it takes a new love and the courage instilled in him by his daughter.



The Third Wheel
5.203

The clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana, but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil with his Taurus, and his planned night turns upside down.



Something's Gotta Give

When perpetually single, aging music industry exec Harry Sanborn, and his latest trophy girlfriend, Marin, arrive at her mother's beach house in the Hamptons, they find that her mother, playwright Erica Barry, also plans to stay for the weekend. Erica is scandalized by the relationship and Harry's sexist ways. But when Harry has a heart attack while there, and the doctor prescribes bedrest, his only option is to stay at the Barry home. Left in the care of Erica and his doctor, a love triangle starts to take shape.



The Grifters
6.5

A small-time conman has his loyalties torn between his estranged mother and his new girlfriend, both of whom are high-stakes grifters with their own angles to play.



Hollywood Ending
6.483

Woody Allen stars as Val Waxman, a two-time Oscar winner turned washed-up, neurotic director in desperate need of a comeback. When it comes, Waxman finds himself backed into a corner: Work for his ex-wife Ellie or forfeit his last shot. Is Val blinded by love when he opts for the reconnect? Is love blind when it comes to Ellie's staunch support? Literally and figuratively, the proof is the picture.



Tramps
Tramps(2016)
6.2

A young man and woman find love in an unlikely place while carrying out a shady deal.



Good on Paper
5.6

After years of putting her career ahead of love, stand-up comic Andrea Singer has stumbled upon the perfect guy. On paper, he checks all the boxes, but is he everything he appears to be?



Meet the Fockers
6.252

Hard-to-crack ex-CIA man Jack Byrnes and his wife Dina head for the warmer climes of Florida to meet the parents of their son-in-law-to-be, Greg Focker. Unlike their happily matched offspring, the future in-laws find themselves in a situation of opposites that definitely do not attract.



Diggstown
Diggstown(1992)
6.289

Gabriel Caine has just been released from prison when he sets up a bet with a business man who owns most of Diggstown, a boxing-mad town. The bet is that Gabe can find a boxer that will knock out 10 Diggstown men, in a boxing ring, within 24 hours. Roy 'Honey' Palmer is that man that, at 48, many say he is too old.

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