In an introductory scene, Leonardo da Vinci is in his studio, working on a variety of projects. The largest, a complex mechanical machine which focuses the sun's rays, is intended to turn lead into steel, but when activated, it turns out that the machine has turned the lead into something far more valuable: gold. Realizing the danger such a machine could wreak, he decides to hide the essential gemstone component, made of three pieces, by hiding them amongst his various works.
In the present, Eddie "Hudson Hawk" Hawkins (Bruce Willis
) is being released from Sing Sing Prison after doing 10 years, presumably for burglary. As he is checking out of prison, he is met by his corrupt parole officer, Gates, who offers to excuse him from community service in exchange for pulling off an art heist. Hudson declines, and meets his buddy (and presumable partner-in-crime) Tommy Five-Tone (Danny Aiello
), who offers him his favorite drink, a cappuccino, but spills it when he slams on the brakes.
The pair return to their old haunt: their co-owned bar Five-Tone in Hoboken, but when Hudson enters, he finds it converted from a comfortable hole in the wall full of working-class regulars, to an elite, upscale urban professional bistro. While attempting to enjoy a fresh cappuccino, he is interrupted by local crime bosses Cesar Mario (Frank Stallone
) and Antony Mario (Carmine Zozzora
), who reveal they are behind the art heist proposed by Gates, and try to pressure Hudson into doing it.
Hudson decides to go through with the heist, and plans the job with Tommy, while his desires to live a straight life fight against it. Sneaking into an auction house, the duo mislead the guards by rewinding the security camera recorders, playing back earlier footage of a quiet building, while Hudson cracks the safe, retrieving a bronze statue of a horse. All the while, the duo are singing a song -- "Swinging On A Star" -- to themselves, separately, in order to keep time with each other. As they reach the end of the song, the guards discover them, but the two manage to escape by jumping off the building's roof.
In a surreal cut-scene, Hudson, statue in hand, finds himself landing in an armchair in Gates' living room, with Gates and the two Marios waiting. Gates gleefully takes the statue from Hudson. Soon, an English butler, Alfred (Donald Burton
) arrives, taking the statue from Gates, admiring it as one of da Vinci's finest works, then smashing it over his head. It shatters, and Alfred retrieves a fist-sized gemstone from the remains. Alfred then dispatches Gates, releasing a switchblade machete from his sleeves and slashing Gates' throat, and then leaves, with the Marios in tow.
The next morning, Hudson appears at the Five-Tone, telling Tommy the story of the previous night, but Tommy is already ahead of him. Reading from the morning paper, he tells Hudson about their heist, which is reported as an attempted
heist, foiled by guards, and the horse statue, the Sforza,
will be auctioned off that night as planned.
Intrigued, and confounded, Hudson rents a tuxedo and attends the auction, where he meets Anna Baragli (Andie MacDowell
), a Vatican antiquities expert, who is invited onstage to verify the authenticity of the statue; to Hudson's bemusement, she does. During the auction for the Sforza,
a flamboyant and impetuous man, Darwin Mayflower (Richard E. Grant
) storms in and declares his bid of $1,000,000. Immediately afterwards, an equally flamboyant and impetuous woman (Sandra Bernhard
) trots in, dog in tow, and declares a bid of $1,000,001, outbidding the man, who is identified as her husband. As the auctioneer calls for closing bids, the man and woman, as well as an assorted cadre of people eating candy bars scattered in the audience, duck; as the auctioneer's gavel hits the podium, it violently explodes, killing the auctioneer and scattering art pieces everywhere. The man and woman promptly leave, unscathed. Meanwhile, Hudson tackles Baragli to save her from a falling column; and is subsequently knocked out by a swinging hung sculpture.
Hudson awakes to find himself in an ambulance, but instead of doctors, is surrounded by the Mario crime family, ecstatic about their latest gig. The Marios are planning to kill Hudson, but instead, he manages to hit the ambulance's driver, and incapacitate Antony with a rack of syringes. Cesar kicks Hudson out of the ambulance, shuttling the gurney he is lying on onto the freeway. The disruption in the ambulance causes it to run offroad and flip over, killing the Marios. Hudson, still strapped to the gurney, manages to dodge traffic and even a toll booth, and direct the gurney to an offramp, before it eventually comes to a stop in the industrial district, where he meets up with a group of characters he recognizes as the candy-eating people from the auction. The first introduces himself as Snickers (Don Harvey
), who shocks Hudson with a cattle prod. Hudson is released from the gurney from a mute man (David Caruso
) who shows him a white card identifying himself as Kit Kat. A young black woman appears (Lorraine Toussaint
), identifying herself as Almond Joy, explaining their names as code names. A tall muscular man with a crew cut (Andrew Bryniarski
) exits a portable toilet, which he accidentally knocks over, and then introduces himself as Butterfinger. Finally, the team is revealed to be led by a seasoned CIA veteran, and former nemesis of Hudson, George Kaplan (James Coburn
). The Sforza
heist is revealed to be part of a CIA sting operation against the Mayflowers, in which Hudson is now an unwilling accomplice. Hudson is knocked out and stashed in a wooden crate of packing peanuts.
Hudson wakes up from his induced sedation, escaping from the packing crate, and finds himself in an ornate room. Looking out a nearby window, he sees the Coliseum; Alfred appears, and welcomes him to Rome. He is taken to the Mayflowers' corporate board room, where Darwin Mayflower announces his plan for world domination via recomposing da Vinci's La Maqunia d'Oro
and convert lead into gold, flooding world markets and making the commodity worthless. The company has reverse-engineered da Vinci's plans for the machine, and have identified the three pieces containing the shards of the machine's essential gemstone; the Sforza
was the first. The second is contained in a secret pocket of da Vinci's Codex,
which is on display in the Vatican.
Hudson visits the Lateran museum in Vatican City to case the joint; while there, he happens into Baragli, who is giving a tour. At the end of the tour, the Codex
is shown, kept it it's own basilica and protected with a glass case and a security cage hanging overhead. Hudson grabs a young girl's toy elephant and flings it towards the case, which triggers proximity sensors, releasing a gas cloud and causing the security cage to suddenly drop over the glass case. Baragli finds Hudson, and brings him through a secret door which leads to the Vatican postal railway. Charming her, he arranges to meet her for dinner. Meanwhile, he has planned out the job to snatch the Codex. While phoning Tommy to tell him about his latest adventure, he manages to miss seeing Tommy, already in Rome, living it up with the Mayflowers just feet away from the phone booth. He runs into Kaplan's team, where Kit Kat warns him about "the blue wire." Snickers informs Hudson that he has to do the Codex job tonight, which he protests, but Almond Joy takes his materials list and the team begins procuring the items.
That night, Hudson sneaks into the Lateran museum, using mirrors to deflect the security lasers, and a fishing pole to hook the Codex
. When a security guard notices the mirrors missing, he runs down the stairs to the Codex, seeing Hudson's setup. Upon reaching the setup, frantically calling for backup, Hudson yanks the Codex
off its plinth, causing the gas to escape and trapping the guard inside the security cage, while Hudson escapes through the glass basilica roof. Running from remaining gendarmerie,
Hudson is chased along rooftops, eventually escaping by falling into a chicken truck, which, it happens, drives right past the restaurant where he is meeting Baragli for dinner. Kaplan's "candy bars" CIA team is also there, watching their table. Baragli fawns over Hudson, and they retreat to her place, where she gets intimate, but she demurely rejects his sexual advances. Suddenly, a secret intercom behind a crucifix in her apartment lights up and sounds an alarm, announcing that there's been a break in at the Lateran museum -- upon which, she trips over Hudson's satchel, revealing the Codex.
Hudson tries to explain, but it turns out Baragli already knows he was going to steal the book, and confronts him with the fact he's working with the Mayflowers. They chat about his role in the Mayflowers' plot, but he insists that he's an unwitting patsy, "just a guy that's good at stealing stuff." Baragli knocks him out with a spiked cappuccino, and the Candy Bars enter; Baragli scolds them for not informing her and "her people" that the Codex
theft was happening that night, and demands to meet with Kaplan.
Kit Kat brings Baragli to see Kaplan, who tries to smooth out the rough edges with her. Upon leaving, she happens to spot the Mayflowers' dog there. After she leaves, Kaplan reveals that he's letting Baragli tag along in order to get closer to the "mysterious Vatican organization" she works with. Later, Baragli is seen in a confessional, talking to a priest, who it turns out is her superior in a clandestine Vatican counter-espionage operation. Upon exiting, she is wearing a nun's habit. She explains to her boss that, while the Vatican organization believes they are working with the CIA in order to stop
the Mayflowers' plan, that in fact the CIA is working with
the Mayflowers to help the plan succeed.
Hudson is brought again before the Mayflowers where he is given the details on his next job, a heist of da Vinci's aerial screw helicopter from the Louvre. Hudson shuts them down, insisting he is not going to do another job for them. They blindfold him, then leave the room; he removes the blindfold to find Tommy, who explains that he was informed of the whole plot ahead of time, thinking it would be a lot of fun and give Hudson a breath of fresh air after his time in prison. Hudson and Tommy get into a struggle over a gun, bursting out of the room, past the Mayflowers and Candy Bars, and off the balcony, onto the ground below, where the gun goes off, and Tommy is shown bleeding. An ambulance appears, taking Tommy and Hudson away; the Mayflowers turn to Kaplan and direct him to execute "Plan B."
The ambulance, then out of sight, drives into a rolling Vatican box truck, and Hudson, Five-Tone (unwounded, but covered in ketchup), and Baragli exit. They retire to Baragli's apartment, confident that the ruse has fooled the Mayflowers and the CIA team. With Hudson no longer working the job, the Mayflowers' plan is thus foiled. Hudson attempts another romantic advance on Baragli, which she again politely declines, to his dismay, asking him (and Tommy) to sleep on the couches.
The next morning, Hudson and Tommy are awoken to find the Candy Bars in Baragli's apartment, with Baragli nowhere to be found. Almond Joy sedates the pair with curare-laced blow darts. Hudson insists that this will still not get him to pull off the Louvre job, but Kaplan tosses him a newspaper, showing that the Louvre was hit the previous night by a well-armed commando team -- Kaplan's team, who stole the da Vinci helicopter in a much more violent and excessive way than Hudson's cat burglar techniques. The last piece of the gemstone is revealed from the base of the helicopter, and Kaplan declares Hudson and cohorts to be "irrelevant." Just then, Baragli enters the apartment, aiming a gun at Kaplan, to Hudson and Five-Tone's joy. However, Almond Joy no-sells Baragli's threat, confident that Baragli won't shoot (over Hudson and Five-Tone's encouragement), because "I've read your dossier, Sister
," and likewise immobilizes her with a curare dart. They then reveal that Baragli is a nun, which everyone in the room knew except for Hudson; Hudson is upset at the deception, but Baragli reveals that she does have special feelings for him.
The Candy Bars take Baragli away, as they need her Vatican expertise for the "next level." However, they don't need two cat burglars anymore, and plan to set timed bombs in the apartment, using a unique adhesive-timed-bomb-launching gun. Hudson and Five-Tone begin to overcome the sedation of the curare, just as Almond Joy is about to re-administer it; they quickly get the jump on her, causing her to swallow a curare dart, immobilizing herself. As Snickers is about to set another bomb, they trip him; causing him to drop the gun, which spins around, launching a bomb onto his head. As Hudson and Five-Tone jump off Baragli's balcony, the bomb on Snickers' head explodes, destroying the apartment, with Snickers and Almond Joy along with it.
Planning to stop the Mayflowers as well as rescue Baragli, Hudson and Five-Tone get to Castle da Vinci, where La Maquina
is being restored, and proceed to breach the grounds, again timing their efforts with a song as they did in the auction house, this time singing "Side By Side." Meanwhile, the Mayflowers and Kaplan are trying to get Baragli to show them how to assemble the three shards into the correct final gemstone for the machine, but Baragli is feigning hallucinations from the curare. They then inform her that (as they believe) Hudson is dead. As the sounds of Hudson's and Five-Tone's breach (using the bomb-launcher taken from Snickers), Kaplan and Butterfinger leave to investigate, leaving Baragli alone with Minerva Mayflower and Kit Kat. Mayflower, with an iron crossbow trained on Baragli, suddenly turns on Kit Kat, shooting him fatally. Kit Kat, in his dying moments, releases Baragli from her bindings; meanwhile, Butterfinger, sent by Kaplan to report back to Minerva, is instead shot by her. Mayflower then returns her aim to Baragli, who overpowers her and escapes. Meanwhile, again at the moment the song ends, Five-Tone is caught by sleeve-machete-wielding Alfred, who takes him to the Mayflower's car, locking him in the back with Darwin, who he punches out. Hudson encounters Kaplan, who begins attacking him with martial arts; he seems to trap Hudson in an induced muscle spasm, but Hudson interrupts it, causing Kaplan to mis-aim a timed flying kick, sending Kaplan off the roof and onto the Mayflowers' car. Then, Baragli shows up -- "We're supposed to be saving you!" "I got bored, so I saved myself!" Meanwhile, with Five-Tone tied up in the back, Darwin leaves the car, and Alfred knocks it into neutral. Darwin calls up tauntingly at Hudson, as the car coasts off a cliff and explodes, with Five-Tone trapped inside and Kaplan on the hood. Hudson is devastated.
Hudson and Baragli are taken inside the castle, where the Mayflowers are stumped, unable to combine the shards into the right gemstone. Hudson takes a shot at it, over Baragli's protests, and eventually crams the shards together into a completed gem. Ecstatic, the Mayflowers put the gem in place, and start the machine, proudly boasting their achievement. Baragli is disgusted at Hudson for helping the Mayflowers win, but Hudson reveals he left out one of the shards, which she happily acknowledges is "very bad." Shortly thereafter, the machine explodes, covering Minerva in molten lead, and burning Darwin to a crisp. Hudson and Baragli run, but are caught by Alfred, who extends both machetes. Hudson fights with Alfred, managing to shove both of Alfred's long knives into one of the castle's thick wooden doors, then slams the door shut, causing Alfred to be decapitated by his own blades. Subsequently, they are blocked by the Mayflower's dog, Bunny, who begins to attack Baragli's neck. Hudson, remembering that Bunny liked chasing tennis balls, takes a tennis pitching machine previously used by Darwin, and, getting Bunny's attention, launches a tennis ball out a window, which the dog gleefully chases out of it. With the castle rapidly catching fire and crumbling from the explosion of the giant gold machine, Hudson and Baragli escape using the da Vinci flying machine, landing eventually in a field near a small village. There, they visit a cafe and talk about their future, Baragli suggesting that God wants her to "keep an eye on him." Baragli mourns Five-Tone, but just then, to their amazement, Five-Tone emerges from a taxi, alive, declaring that the Mayflower's high-end town car had an interior fire suppression system, saving his life. With friends alive, love interest kindled, and having successfully defeated both the Mayflowers and the Candy Bars, Hudson finally gets to drink his cappuccino.