Boomerang (1992)

Halle Berry plays the artist Angela Lewis

Boomerang on IMDB

The film begins as Marcus Graham (Eddie Murphy) enters Chantress, the company that he works for as an advertisement executive. It is quickly established that he is quite the ladies' man, as he tells his assistant to send flowers to nine different women, with cards reading "only thinking of you." When he enters his office, Nelson (Geoffrey Holder), one of the creative minds also in Marcus' department, shows Marcus a re-cut he's done of one of the ads they've been working on. Marcus tells Nelson, who's very creative but also very risqué and overtly sexual with his style, that he must re-edit the ad, as some of the material may be offensive to women. Nelson reluctantly agrees, then leaves.
The next day, Marcus meets Lady Eloise (Eartha Kitt), the head of the company which will soon be acquiring Chantress in a business merger. She suggests that Marcus may be promoted to head of the marketing department, and invites him to her home for dinner that evening. Marcus realizes she intends to have her way with him, and thinking of the promotion, goes through with it and spends the night with her. The next day at work, he meets Jacqueline Broyer (Robin Givens), a beautiful woman who he realizes is going to be given the job he wanted, and will soon become his boss. At the party being held for the companies' merger, Marcus tells his friends Tyler (Martin Lawrence) and Gerard (David Alan Grier) he's thinking about resigning since he's not going to be promoted. While there, Jacqueline introduces him to Angela Lewis (Halle Berry), who works in the art department, and tells him the two of them should be working together. Also, everyone in the party is introduced to Strangé (Grace Jones), the wild fashion diva who's been chosen as the new face of Lady Eloise Cosmetics. While looking for Jacqueline, Marcus bumps into Angela, and when he spots Jacqueline, introduces Angela to Gerard so that he can go and catch up with her. When he attempts to woo Jacqueline, she tells him she doesn't date co-workers. Marcus however still believes he will be made the exception because of her flirtatious nature towards him.
Some time later at the office, Jacqueline tells Marcus they should go over some of their work together, and Marcus suggests they do it at his place over dinner, to which Jacqueline agrees. Marcus also finds out that Angela and Gerard will be going out that night. Both couples meet that evening, and ironically, Gerard, who's not as successful with women as Marcus, ends up having the better evening with Angela, while Jacqueline and Marcus eat dinner in front of the TV, which doesn't leave much time for the two to establish any sort of chemistry. Later, the two are sent on a business trip in New Orleans, and they eventually have sex while there.
Marcus, who assumes that he and Jacqueline are now a couple, is rather shocked to find that Jacqueline feels they should take it slowly, and isn't as enthusiastic about their relationship as he. While he feels he's falling in love, he doesn't understand how she can be so careless and inconsiderate about his feelings. After Marcus finds out that Jacqueline has told some of their personal business to Strangé, he tells her that the two of them should take a break for a while. Jacqueline gets the last word however, when she bluntly tells Marcus "it's over." Distraught about their breakup, Marcus' work ethic begins to lag, and after he ruins a major business proposal, Jacqueline decides rather than fire him, she'll give him a few weeks off work to get himself together.
During this time, Marcus begins to hang out with Angela, who tries to help bring him out of the funk he's in. On Thanksgiving, Marcus, Angela, Tyler, Gerard and his parents get together for dinner. While eating, Angela and Gerard tell his parents that they aren't a couple, when his father assumes that the two are. When everyone else leaves, Marcus and Angela clean up, and fall asleep on the couch together. When they wake up, the two begin to make out, and assumedly sleep together. While out with Gerard and Tyler, Marcus tells Gerard that he and Angela are going out together, which upsets Gerard, knowing Marcus' past with women.
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Spiral (2007)

Joel Moore plays artist Mason (as Joel David Moore)

Spiral on IMDB

A reclusive telemarketer and aspiring artist makes a friend, sketches a portrait of said friend, and has a massive mental breakdown.
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Tokyo Cowboy (1994)

Christianne Hirt plays artist Kate Beatty

Tokyo Cowboy on IMDB

A young Japanese man heads to Canada to meet his childhood penpal and to fulfill his dream of becoming a cowboy. In their letters as children she claimed to be a cowgirl, now she is grown up and an artist living with her sister.


The Caveman's Valentine (2001)

Colm Feore plays artist David Leppenraub

The Caveman's Valentine on IMDB

A former family man and pianist studying at Juilliard music school, Romulus Ledbetter (Samuel L. Jackson) is now suffering from paranoid schizophrenia and living in a cave in Inwood Park, New York. He believes that a man named Cornelius Gould Stuyvesant is controlling the world with rays from the top of the Chrysler Building, and that his mind is inhabited by moth-like angels. On Valentine’s Day he discovers the frozen body of a young man, Scotty Gates (Sean MacMahon), left in a tree outside his cave. The police, including Romulus's daughter Lulu (Aunjanue Ellis), dismiss the man's death as accident however, a homeless ex-lover of Scotty tells Romulus that he was murdered by the famous photographer David Leppenraub (Colm Feore). Determined to discover the truth behind Scotty’s death and prove his worth to his daughter, Romulus manages to get an invitation through a former friend to perform one of his compositions at Leppenraub’s farm. What unfolds thereafter is a twisted tale of mystery, deception and a man's struggle against his own mind.
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The Science of Sleep (2006)

Gael García Bernal plays artist Stéphane Miroux
Charlotte Gainsbourg plays artist Stéphanie

The Science of Sleep on IMDB

Stéphane Miroux (Gael García Bernal) is a man whose vivid dreams and imagination often interfere with his ability to interact with reality. He is coaxed back to his childhood home after his divorced father passes away and his mother finds him a job in a calendar printing company in France. His mother (Miou-Miou) implies the position is a creative role, and he prepares colourful drawings, each showing a disaster, for his "disasterology" calendar. However, nobody appreciates his talents and it transpires that his mother had led him on - the real vacancy is for nothing more than mundane typesetting work. While leaving his apartment to go to work one day, Stéphane injures his hand helping his new neighbor move a piano into her apartment. The new neighbor, Stéphanie (Charlotte Gainsbourg), invites Stéphane into her apartment (unaware that he lives next door) where her friend Zoé (Emma de Caunes) tends to his wound. Stéphane initially forms an attraction to Zoé, though he suspects it is instead Stéphanie who likes him.
Stéphane realizes that Stéphanie, like him, is creative and artistic. They plan a project for use in a short animated film. Following the advice of Guy (Alain Chabat), Stéphane's sex-obsessed co-worker, Stéphane pretends that he isn't Stéphanie's neighbor, pretending to leave the building when he leaves her apartment. That night, when he is sleepwalking he writes a confusing note to Stéphanie that asks for Zoé's phone number. Stéphane realizes his mistake upon waking and retrieves the letter with a coat hanger, unaware that Stéphanie has already read it.
Surrealistic and naturalistic elements begin to overlap, and the viewer is often uncertain of which portions constitute reality and which are merely dreams. One such sequence, in which Stéphane dreams his hands become absurdly giant, was inspired by a recurring nightmare director Michel Gondry had as a child.[3] Stéphane becomes more enamoured with Stéphanie as he spends more time with her and shares his many inventions with her. He gives her a "one-second time machine". Stéphane's dreams encroach on his waking life as he tries to win Stéphanie's heart and misses time at work. He breaks into Stéphanie's apartment, takes her small, stuffed horse toy and implants a galloping mechanism. While putting it back into her apartment, Stéphanie arrives and catches him, shocked, calling him "creepy." Embarrassed and heartbroken, Stéphane retreats to his apartment where he receives a call from Stéphanie who apologizes and thanks him for the gift she discovers: a galloping version of "Golden the Pony Boy," named after Stéphane.
Waking and dreaming become even more intermixed. To Stéphane's surprise, the calendar manufacturer accepts his "Disastrology" idea and it becomes a great success. A party is thrown in his honour, but he becomes depressed and begins drinking excessively after he witnesses Stéphanie dancing flirtatiously with another man. Stéphane and Stéphanie then have a confrontation in their hallway when Stéphane announces that he doesn't want to be Stéphanie's friend any longer. Stéphanie becomes very upset, offering Zoé's phone number and reciting Stéphane's note. Stéphane, still unaware that Stéphanie has read the note, assumes that they are connected through "Parallel Synchronized Randomness", a rare phenomenon he has examined in his dreams. Stéphanie offers that they discuss their issues on a date, but on Stéphane's walk to the café to meet her, he has a frightful vision that she isn't there and she doesn't love him. He runs back to her apartment and bangs on her door, demanding that she stop torturing him, though, in actuality, she is indeed waiting for him at the café. Stéphane runs at her door, attempting to break it down, but winds up bashing his head and collapsing in the hall, bleeding, where his mother eventually finds him. Tired of waiting, Stéphanie returns home while Stéphane, coaxed by his mother and her friend, decides to move back to Mexico.
Before leaving, Stéphane's mother insists that he say goodbye to Stéphanie. In his attempt to do so, he becomes extremely crass making sexual and otherwise offensive jokes to her, and accusing her of never being able to finish something she starts. Yet he reveals that he is truly interested in her because she's different from other people. As his antagonistic behavior pushes her to her breaking point, Stéphanie asks Stéphane to leave but he instead climbs into her bed and yells at her, before spotting two items on her bedside: his one-second time machine, and the boat with the forest inside of it - finished.
Stéphane falls asleep in Stéphanie's bed. As she checks on him to see why he has become so quiet, she gently strokes his hair. The film closes with Stéphane and Stéphanie riding Golden the Pony Boy across a field before sailing off into the ocean's horizon in her white boat.
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