Mr. Jack proposes the philosophical ideology; the greatest sin against the natural order is to deny one’s true nature, no matter where it takes us. In suicide, one curtails one's existence, yet when one denies one's nature, we corrupt all which one cherishes. Mr. Jack is the story of Val Shepard, an artist returning to New York after a self-imposed exile who tells the story of Mr. Jack. Upon his return, Val takes on the role of an observer, metaphorically coming back from the dead to see how life had moved on in his absence. Yet, unlike the dead, Val begins a manipulation of the present that he believes will undo his past.
Thematically, Mr. Jack addresses questions of self-awareness and the cause and effect of the denial of self. Val is the anti-hero, unable to face his innermost wants and desires, he lives vicariously through the carefree Jackson King 'Mr. Jack', and in denying his true nature, Val destroys all that he cherishes.
After a self-imposed exile, artist, Val Shepard, returns to New York City with the intention of picking up the life he left behind. Nowhere to go, he arrives on the doorstep of his ex-landlord, and father figure, Jimmy Alfano. With no units available, Jimmy allows Val to stay in the vacant custodian's storeroom across the hall from his old studio.
Val soon learns that life on the Lower East Side has moved on without him, yet nonetheless attempts to reconnect with his girlfriend Jenna Bardi. After leaving her without warning, Jenna wants nothing to do with him. Val tries explaining why he went, but Jenna tells him that it’s too late, she’s moved on with her life.
Thinking he can win her back, Val asks to see her one last time under the guise of obtaining closure. Jenna refuses yet after his relentless persistence, agrees to one final meeting. Upon arrival at her apartment, Val is surprised to see they are not alone. Jenna introduces Val to her new friend Lara, and to Ian, Jenna’s new husband.
Val is taken aback by the news. Further to add insult to injury, Val learns Ian is a successful painter and holding a show in a few months at the prestigious Turner-Prince Gallery. The same gallery where Val would have shown had he not sabotaged his career. Realizing he has lost Jenna, Val capitulates, and as he is about to leave, the disastrous dinner is interrupted by a phone call.
The call sparks an argument between Jenna and Ian, and as they bicker in the kitchen, Lara informs Val, the call is from Ian’s lover, Ruta. With her short marriage already in jeopardy, Val feels maybe he still has a chance and takes Ian up on an offer to hang out, only as a possible opportunity to obtain dirt on Ian. Which Ian, in his arrogance, does in an unabashed manner.
Val eventually meets the new occupant of his old studio, Jackson King, who claims to be a painter as well. Jackson lives a decadent lifestyle, using heroin and throwing extravagant, well-attended, Warholesque parties. Val begins to admire Jackson and live vicariously through him, ignoring his career and responsibilities.
After one of Jackson's parties, Val brings a girl back to his room. The next morning he discovers she has robbed all of his money. With no one else to turn to, Val asks Jenna for a loan. When she arrives at his room to deliver the money, Val confronts her about Ian infidelity. Jenna admits to Val, she knows but doesn’t care. This news devastates Val even further. As she is about to leave, Jenna meets Jackson. The two have an instant attraction for each other.
Val then conjures the idea, if Jenna were to get involved with Jackson it may bring her fragile marriage to an end. Val begins to encourage Jenna to have an affair with Jackson, going as far to fascinate their first date. And while Jenna and Jackson start seeing each other, Val begins to date Jenna’s friend Lara in hopes to hear gossip about them.
Val discovers that Jackson is not an artist, but a fraud, he plagiarized his artwork. At first furious with Jackson, Val tells him to continue the charade rather than admit his plagiarisms to Jenna who Val feels is not quite ready to leave Ian.
Suspecting his wife’s infidelity, Ian shows up at Jackson's studio with two gallery owner patrons. Ian invites Jackson out for drinks with them in hopes Jackson will implicate himself. While they are out Jackson gets sick from a dirty shot of heroin and must cut the evening short, narrowly escaping with Val’s assistance.
Not wanting to be upstaged by Ian, Jackson throws a party a few days later to show off to Ian. During the party, Jackson tells Jenna he has fallen in love with her and ask’s her to leave Ian. Jenna leaves the party with Ian, and without giving Jackson a definite answer.
Convinced now that his wife has been unfaithful, Ian arrives at Jackson’s studio with his lover Ruta to confront him and Jenna. Ian tells Jenna to choose between him and Jackson. She picks Ian. The decision devastates Jackson who walks out of his studio in despair.
Val sees Jenna home, and Ruta and Ian stay behind in Jackson's studio. Ian and Ruta have one final fling, during which, Ian unintentionally shoots Ruta with an overdose of heroin leaving Jackson and Val with the corpse. Believing they have no other option, Val and Jackson dump Ruta’s body near the East River.
After they dump her body, Val takes Jackson home before paying a visit to Jenna and Ian. Jenna refuses to let Val see Ian and asks him if he has taken care of everything. Val asks her how she can be so callous when a young girl has just died. Jenna tells Val, she knows nothing about it. There was no involvement by her and Ian, and Val should just forget about it. Val asks her, how he could ever have been in love with a woman like her. Jenna tells him, he should have never have come back to New York and should have stayed gone.
On his way home Val realizes, although a plagiarist, Jackson is the most sincere man he has ever known and is looking forward to seeing him. When Val arrives at his home, he finds police cordoning off the building with crime scene tape. Upon learning of his wife’s death, Ruta‘s husband Peter tracked her down to Jackson's studio. Thinking he was his wife's killer, Peter threw Jackson off of the roof.
Although Jackson’s parties were well-attended, his funeral is sparse. Apart from a few curiosity seekers the only attendees are Jimmy, Val, and Jackson’s uncle, Jedidiah. After the funeral, they return to Jimmy’s, and the three men raise a toast, to Jackson King.
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