Bill Sykes is the main antagonist from Disney's 1988 movie, Oliver & Company. He is based on the Bill Sikes of Charles Dickens' Oliver Twist, of which the film is a modern reimagining. This Sykes is a Mafia crime boss who operates out of a warehouse by the docks and the owner of two Dobermans, Roscoe and DeSoto.
Sykes is a big muscular man who is roughly in his early sixties. He is half bald, has grey hair, and as well as this, he wears spectacles. He smokes large cigars and is always seen in a sharp suit to further emphasize his role as an intelligent businessman in command of the situation, and not merely some common thug taking orders from someone else (a rather stark contrast to the character he's based on). Because of his smoking, Sykes speaks with a hoarse voice which makes his character more menacing.
Sykes is one of Disney's most heavy-set villains, shown usually in shadows like most stereotypical villains. He is brutal, shadowy, sarcastic, psychotic, impatient, uncaring, clean-shaven, eerily charming, evil, cruel, slightly naive, cunning, opportunistic, murderous, ruthless, greedy, sadistic, and villainous.
Unusually for Disney, the lifestyle and behavior of a mob boss is not glamorized or made more child-friendly. Beneath his businessman-like exterior, Sykes is clearly a ruthless, brutal murderer - during a scene with Fagin, he is heard clearly on the phone discussing with a supposed underling about their manner of torturing and murdering some unknown victim. He appears to know anyone important and wealthy in New York City, even their home addresses and phone numbers, as seen when he calls the Foxworth estate to begin the ransom.
His minions in the movie are his two Dobermans, Roscoe and DeSoto, which he takes care of a lot; however, in the final chase, he was so determined to get Jenny back, he didn't notice that his dogs died and even if he did, he didn't seem to care.
Sykes has lent a large amount of money to the petty criminal Fagin for some unknown reason, sending his two evil Dobermans, Roscoe and DeSoto, to tell Fagin to go up and meet with him. Fagin, unfortunately, finds himself unable to pay the money back and begs for more time. Sykes tells him that he has three days to find the money or else who knows what will happen to Fagin, his home, or his dogs. Then, he honks his horn to call his dogs back, startling Fagin, causing him to lose his balance and fall off the dock and into the Hudson River.
When Fagin learns that Oliver's new owner is exceedingly wealthy, he orders "Mr. very rich cat-owner-person" to bring him lots and lots of money in return for the cat. He tells Sykes about the plan; at first awkwardly which causes Sykes to lose his patience and snap his fingers to order his dogs to attack him when they are actually confronting one of Fagin's dogs, Dodger.
But during the attack, Fagin is able to tell him the plan in a loud and proper way this time and shows him Oliver as proof which convinces Sykes and causes him to snap his fingers to cease the attack. Upon recognizing the Foxworth family address on Oliver's collar, Sykes makes the assumption that this is a ruse to in fact to kidnap and ransom the cat owner instead of the cat. He congratulates Fagin and gives him one more chance with only 12 hours left when feeding biscuits to his dogs, while Fagin and Oliver come to Dodger's aid after Dodger lays injured and unconscious with severe (but invisible) injuries from the attack.
When Jenny Foxworth comes to get Oliver, she shows Fagin that all she has brought with her is her piggy bank, with Sykes and his evil dogs unknowingly watching from afar in his Cadillac. When Sykes sees Fagin abandoning the plan by freely handing Oliver back to Jenny without asking for the ransom money, he seizes his chance. Driving up, he pulls Jenny by the arm into his car, and takes her to his warehouse after throwing Oliver out the window. Sykes tells Fagin to keep his mouth shut and consider their account "closed".
Later, Sykes ties a crying Jenny to a chair in the center of his office, taunting her about his dogs, cruelly joking that he'll have his dogs eat her if her parents don't pay the ransom.
He hears a strange sound and sends Roscoe and DeSoto to check it out. While watching Jenny, Sykes calls the Foxworth family's butler, Winston, and tells him to call Jenny's father. Oliver, Dodger, and the gang follow them to the warehouse, where they find out that Jenny is being held for ransom.
When Tito, Einstein, and Francis manage to distract Sykes by dressing up as a pizza delivery guy, Sykes is shown loading a handgun, acknowledging that he did not order any pizza. When Sykes walks away to look for his dogs, Oliver, Dodger, and the gang manage to enter his office. Finally, Sykes finds his dogs trapped under a net and frees them. When Sykes with his dogs returns and finds the door locked, he believes it was Jenny's doing and warns her to open the door. Oliver and the gang manage to pull Jenny up into a higher part of the room, with the help of a crane and Tito's electric specialties, before Sykes, Roscoe, and DeSoto burst through the door.
But just when it looks like they're home free, Sykes takes out an emergency fire axe and destroys the crane's controls, thus, causing Oliver and the company to fall and land on a long slide. At the end of the slide, Sykes and his dogs confront them, as the evil mafia boss prepares to signal his dogs to attack. Before he can however, Fagin bursts through the window on his scooter and the gang, along with Jenny, hop on and drive away as fast as they can. Sykes and his dogs follow them in his car. Fagin goes onto the subway tracks, hoping that Sykes can't follow them... but he does either way.
Now driving like a maniac (and not thinking rationally, as he doesnt even seem to consider the danger), Sykes pulls the gear stick so hard that it breaks off and then steps hard on the gas. He goes at full speed, causing his car's tires to wear away and run on the tracks. He bumps into Fagin's scooter, causing Jenny to fall onto his hood. He then punches his hand out of the window and grabs her by the arm. However, Oliver notices this, jumps onto Sykes' hand and bites it. But Sykes throws him into the backseat with Roscoe and DeSoto.
Dodger manages to jump on and fights off Roscoe, while Oliver fights off DeSoto, causing the two Dobermans to fall onto the electrified tracks and killing them. Sykes pays no attention as to what happened to his dogs and continues to chase the gang. He goes up through his car roof and grabs Jenny by the leg, trying to pull her back in. Just as he is pulling her back in, Dodger and Oliver jump onto Sykes and fight him off, causing him to lose his grip on Jenny. Even as he manages to throw them off, Sykes turns to see a train heading straight for him just before his car collides with it, killing him in a fiery blaze and sending the remains into the Hudson River.
- Sykes is clearly seen loading a handgun. So far, this is the first time in Disney history where a modern gun has been loaded.
- Robert (Salvatore) Loggia is famous for playing the role of gangsters and mob bosses, including a gangster named Salvatore (his actual name) "The Shark" Macelli in Innocent Blood.
- Sykes is the last male villain until Hades to not sing a song. Percival C. McLeach technically didn't have an original number either, but he was heard singing a parody of "Home on the Range" in one scene and one of "The Crawdad Song" in another.
- Along with Roscoe and DeSoto, (both electrocuted by the third rail of the subway), Sykes' death is one of the more graphic deaths in Disney history.
- Sykes appears as more of a main antagonist to Fagin while Roscoe and DeSoto are secondary antagonists to him.
- In the original novel, Sykes' original name is written as "Sikes" and he had only one dog, a bull terrier named Bull's Eye whom he would beat until the dog needed stitching.
- Sykes' appearance may have been an inspiration for John Silver as both are pot-bellied, tall, and some of their facial expressions are similar. Also, both were animated by Glen Keane, which could also explain the same physical appearances. And also in the 1990's Swedish redub, they had the same voice actor.
- Marlon Brando was offered the role of Sykes by the head of the Walt Disney Company Michael Eisner himself. Brando, however, turned it down, fearing the movie would bomb.
- Sykes shares similarities to The Hangover Part III villain, Marshall as both are mafia bosses, don't get what they want back (Sykes wanted his money back, and Marshall wanted his gold back), both kidnap another character in their respective movie (Jenny in Sykes' case, and Doug in Marshall's case), give other characters a few days to get back what they are after and die near the end of their respective films. Unlike Marshall, Sykes has no minions (though his dogs may count as such). Interestingly, both characters have dogs that are guard dogs (Dobermans in Sykes' case, and Rottweillers in Marshall's case).