Dick Tracy 1990

In the seedy underbelly of the city, an unsuspecting young street urchin, Kid (Charlie Korsmo), stumbles into a bloody massacre orchestrated by two ruthless enforcers for Alphonse “Big Boy” Caprice (Al Pacino), a crime lord hell-bent on dominating small businesses. As Detective Dick Tracy (Warren Beatty) closes in on the scene of the crime, he apprehends Kid for petty thievery and takes him under his wing, along with his girlfriend Tess Truehart (Glenne Headly). Meanwhile, Big Boy coerces Club Ritz owner Lips Manlis (Paul Sorvino) into signing over the deed, then brutally murders him and steals his sultry singer girlfriend Breathless Mahoney (Madonna), who becomes the only witness to Lips’ demise.

As Tracy delves deeper into the case, he interrogates Lips’ three hired guns - Flattop (William Forsythe), Itchy (Ed O’Ross), and Mumbles (Dustin Hoffman) - before paying a visit to Club Ritz to arrest Big Boy for murder. Breathless attempts to seduce Tracy in exchange for her testimony, but ultimately fails, leaving Big Boy free to continue his reign of terror.

Big Boy’s next move is to gather a motley crew of criminals, including Spud Spaldoni (James Caan), Pruneface (R. G. Armstrong), Influence (Henry Silva), Ribs Mocca, and Numbers (James Tolkan), under his leadership. However, when Spud refuses to join forces with Big Boy, he meets a gruesome end at the hands of a car bomb, leaving Tracy wondering what’s unfolding.

Big Boy and his henchmen next kidnap Tracy, attempting to bribe him into silence. When Tracy refuses, they try to kill him by rigging a boiler to explode, but Kid intervenes once more, saving Tracy’s life.

As Tracy tries again to secure Breathless’ testimony, she agrees only if he gives in to her charms. Despite his growing attraction, Tracy resists, leading to a series of events that culminates in a seemingly unsuccessful raid on Club Ritz - actually a diversion for officer “Bug” Bailey (Michael J. Pollard) to install a listening device and gather evidence against Big Boy’s criminal empire.

As the dust settles on the decimated remnants of Big Boy’s criminal kingdom, a sense of vulnerability washes over the once-feared gangster. His attention turns to Bug, whose capture serves as the perfect trap for Influence and Pruneface to exact their twisted revenge upon Tracy in a dimly lit warehouse. The ensuing gun battle is a chaotic symphony of gunfire and screams, until a mysterious figure emerges from the shadows - known only as “The Blank” - to rescue Tracy from certain death at the hands of Pruneface. Influence slips away into the night, but not before leaving behind a trail of destruction and despair.

Meanwhile, Breathless reappears in Tracy’s life, her intentions as duplicitous as ever. Despite his better judgment, Tracy finds himself succumbing to her charms, and their kiss is a fleeting moment of passion before Tess, witness to the betrayal, flees town with a heavy heart. However, it soon becomes apparent that Tess has undergone a change of heart, only to be snatched away by The Blank - aided by 88 Keys, the cunning club piano player (Mandy Patinkin) - and spirited out of the city.

Tracy falls prey to another trap, this time finding himself drugged and framed for the murder of corrupt District Attorney John Fletcher (Dick Van Dyke). Big Boy, freed from prison on New Year’s Eve by his loyal cohorts, sets out to reclaim his criminal empire. However, he too is framed - this time for Tess’ kidnapping - leaving Tracy with no choice but to spring into action and rescue his beloved.

As the clock strikes midnight, Tracy joins forces with Kid, now rebranded as Dick Tracy, Junior, to take down Big Boy’s operation. The ensuing showdown outside Big Boy’s club ends in disaster, with most of the crime lord’s henchmen meeting their demise at the hands of the police and Tracy himself (only Mumbles and 88 Keys manage to escape arrest). In a desperate bid to evade capture, Big Boy flees through a network of tunnels, eventually finding himself trapped on a drawbridge suspended high above the city. As he frantically searches for an exit, he becomes aware that Tess is being slowly crushed by a gear mechanism - his own doing, no less.

Big Boy’s attempts at escape are short-lived, as he is confronted by both The Blank and Tracy. In a stunning turn of events, The Blank orders Tracy to put Big Boy out of commission, but the gumshoe hesitates, sensing that something is amiss. As tensions escalate, The Blank raises his gun to Tracy, only for Kid to intervene, tackling the mysterious figure in a daring display of bravery.

As chaos erupts around him, Big Boy seizes his firearm and unleashes a hail of bullets at the Blank figure, only to pivot and aim the gun at Tracy in a desperate bid for freedom. But Tracy refuses to back down, charging forward with unyielding determination and sending Big Boy tumbling towards the drawbridge’s deadly gears. In the ensuing chaos, Junior makes a valiant attempt to free Tess from her precarious perch on the brink of the gears, but Tracy swiftly takes control, and the star-crossed couple clings to each other in a desperate bid for survival.

As the dust settles, Tracy is finally able to uncover the Blank’s true identity beneath the mask: his shock and horror give way to revelation as he discovers that the faceless figure is none other than Breathless Mahoney, who recounts her doomed attempt to assert control over the city before succumbing to her last breath with a kiss that leaves Tracy reeling. With the truth finally out in the open, Tracy’s name is cleared of any wrongdoing in regards to Fletcher’s murder.

Later, as he prepares to pop the question to Tess, Tracy’s romantic moment is interrupted by a brazen robbery in progress, prompting him to spring into action alongside Dick Tracy Jr. As they take off to confront the would-be thieves, Tracy pauses just long enough to place a treasured red box containing an engagement ring into Tess’s waiting hands, whereupon she slips it onto her finger with a radiant smile before the pair departs to face whatever dangers lie ahead.