As the film opens, the audience is greeted by the melancholic tones of "The Clouds Will Soon Roll By," a fittingly somber song reflecting the hardships of the Great Depression, as rain pours down over 1934 Chicago. The narrative begins with Arthur Parker, portrayed by Steve Martin, being rudely awakened by an alarm clock. In his attempt to rekindle some intimacy with his wife Joan, played by Jessica Harper, he is met with rejection as she turns him down, revealing her disinterest in their relationship. This leaves Arthur frustrated by both his wife’s coldness toward sex and her refusal to assist him financially in his dream of opening a sheet music store.
Determined, Arthur storms out of the house, vowing never to return. At the bank, he attempts to secure a loan from the banker, Mr. Perkins, a role played by Jay Garner, to help fund his aspirations. Unfortunately, lacking collateral, his request is declined. In these moments of disappointment, Arthur finds solace in elaborate musical fantasies, escaping reality through joyous song-and-dance sequences reminiscent of Busby Berkeley. A standout scene features Arthur and the banker lip-syncing "Yes, Yes! (My Baby Said Yes)," accompanied by an enchanting chorus line of dancers, creating a kaleidoscope of movement and sound that symbolizes Arthur's dreams.
As the story progresses, Arthur encounters a hitchhiker known as the Accordion Man, portrayed by Vernel Bagneris. Arthur's journey continues to unravel when he meets Eileen, a bashful school teacher played by Bernadette Peters, while selling sheet music at Barrett's Music Shop. He is immediately captivated, singing a tender tune, "Did You Ever See a Dream Walking?" which transforms her into a more glamorous version of herself for a delightful tap dance routine. However, Eileen remains aloof, leaving Arthur longing for more than just a fleeting connection.
Following this brief encounter, Arthur shares a meal with the Accordion Man, and we watch as reality blurs with fantasy once more. In a whimsical sequence, Arthur imagines the walls of a diner dissolving away as he dances to "Pennies from Heaven," symbolizing his hope amidst the downpour of life's struggles. Arthur's affection for Eileen grows, and he seeks her out, only to stumble into the complexities of love and desire.
Arthur's life becomes a whirlwind of surreal escapism, punctuated by moments of stark reality, as she faces the repercussions of her pregnancy. He finds himself running a struggling record shop, drowning in disappointment as Eileen's life begins to spiral, culminating in her drastic decision to sell herself to survive. Amidst the chaos, Arthur finds he's entangled in a web of moral ambiguity and betrayal, as he struggles to reconcile his obligations to Joan with his intense feelings for Eileen.
At a pivotal moment, the film hints at a darker turn when Arthur discovers the fallout of his actions coinciding with violent events outside his control. While grappling with betrayal and tragedy, he fights for redemption, vowing to change after witnessing the horrific aftermath of a crime linked to his chaotic life. In a moment suspended between hope and despair, Arthur expresses anger and desperation but ultimately wraps himself in a world of upbeat numbers, transitioning from tragic to comedic, encapsulated by the song "Life Is Just a Bowl of Cherries."
The culmination of Arthur's journey leads him to face the music—a metaphor for the choices he's made. As the narrative weaves through trials and tribulations, Arthur and Eileen slip into fantastical sequences that bridge the gap between illusion and reality. At a critical juncture, Arthur's conviction for murder resonates as he faces the gallows, reflecting on the dreams that led him astray. He quotes lyrics from "Pennies from Heaven" with a poignant sincerity, reminding viewers of the thin line between reality and fantasy.
In a climactic finale, Arthur defies the expectations of his fate, declaring, > "Whoever said you could stop a dream? We couldn't go through all that without a happy ending." This moment transitions into an exuberant closing number, “The Glory of Love,” with vibrant choreography, and a symbolic rainbow emerging, signifying hope amidst despair. The film concludes with echoes of "Pennies from Heaven" and “Love Is Good For Anything That Ails You,” enveloping the audience in a delightful musical embrace as they ponder life’s unpredictable journey.