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, cunning, evil, cruel, and ruthless.
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. Sykes, upon recognizing the Foxworth family address on Oliver's collar, assumes this is a ruse to in fact to kidnap and ransom the cat owner, rather than 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, pulling Jenny into his car, and taking 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 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. Sykes, driving like a maniac, pulls the gear stick so hard that it breaks off, then steps hard on the gas, and 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. But Oliver jumps on and bites Sykes' hand, 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, grabs Jenny's leg, and tries 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.
- "The money, Fagin."
- "Oh boy, oh boy, oh boy..."
- "I don't want your garbage, Fagin."
- "I don't think you grasp... the severity of the situation."
- "Mr. Fagin! Now, I lent you money and I don't see it. Do you know what happens when I don't see my money, Fagin? People get hurt. People like you get hurt. Do I make myself clear?"
- "Three sunrises. Three sunsets. Three days, Fagin."
- "No, Fagin. Three."
- "Yeah, who is it?"
- "Fagin, it's you. Why didn't you say so?"
- "Don't be silly. Just push the door."
- "I said, push!"
- "What do you mean? You start with the knuckles."
- "Ah, Fagin. Do come in. I'll be right with you."
- "Yeah. No, you don't kill 'im yet. Huh? Yeah. And then, what's... what's the last thing you do? You put on the cement shoes. Yeah. Yeah, yeah, that's right. Come on. Hey, don't worry about it."
- "So, Fagin. Did we bring something green and wrinkly to make me happy?"
- "Oh boy, oh boy, oh boy..."
- "What am I gonna do with you, Fagin?"
- "Fagin. You don't got the money..."
- "Hey... I think there's hope for you yet. Oh-ho! I'm proud of ya, Fagin. Yeah. You're startin' to think big. You've got 12 hours. And, Fagin? This is your last chance..."
- "Easy, boys..."
- "Keep your mouth shut. Consider our account closed."
- "Now, don't cry, little girl. They only eat when I tell them to."
- "Roscoe. DeSoto."
- "Yeah. Oh, that's funny, Mr. Winston. But I don't think you really appreciate the situation. Somebody could get hurt. Just get the old man on the phone and tell him it's about his daughter... Jenny."
- "What the..."
- "I didn't order any pizza."
- "Where are those dogs?"
- "What is this, a slumber party? Get goin', ya stupid mutts!"
- "What is this?"
- "All right, girlie. Open the door. Come on, now. Girlie, I'm warnin' ya."
- "You just... Back up. DeSoto. Come on!"
- "Come on."
- "This has all been very entertaining. But the party is over."
- "FAGIN!!!" (his last words)
- 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 some railroad tracks) Sykes' death is one of the more graphic deaths in Disney history.
- Sykes is similar to Percival C. McLeach. Both are the main antagonist, kidnap children (Sykes, Jenny, and McLeach, Cody), both have pets that serve as the secondary antagonist (Sykes, Roscoe and DeSoto; McLeach, Joanna the Goanna), like money and both possess firearms however Sykes possesses more modern weaponry his weapon being a handgun and McLeach's being a Winchester Model 1912. In the climax both get killed (Sykes' car explodes and McLeach falls down a waterfall.).
- Sykes is also similar to Madame Medusa. Both of them live in New York. They also are the main antagonist, impatient, kidnap young girls (Sykes: Jenny, Medusa: Penny) for greedy reasons (money for Sykes and the Devil's Eye for Medusa), both have male pets that look alike (Roscoe and DeSoto for Sykes and Brutus and Nero for Madame Medusa), and both would do anything to get their way. In the climax, they chase the animals that save the ones they kidnapped (in Sykes' case, Oliver, Dodger, and the gang; in Medusa's case, Bernard, Miss Bianca, Ellie Mae, and the swamp folks).
- 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.
- Sykes may have inspired Carface from the animated film All Dogs Go to Heaven as they both have much in common. Both smoke cigars, both kidnap young girls (Sykes, Jenny and Carface, Anne-Marie) and both run a business. However unlike Carface, Sykes didn't fall in love with Jenny and took care of his henchmen; Carface often abused Killer and tried to kill him at times and unlike Sykes who had only two dog henchmen, Carface had a gang. They also speak in hoarse voices although Carface only spoke with a hoarse voice in the first All Dogs Go to Heaven film his first voice actor Vic Tayback died in 1990 so he was replaced by Ernest Borgnine and from then Carface spoke with a softer voice. Furthermore, they both taken by Italian voice actor, Glauco Onorato.
- 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 both die near the end of their respective films. Unlike Marshall, Sykes has no minions though his dogs may count. Interestingly both characters have dogs that are guard dogs (Dobermans in Sykes' case and Rottweillers in Marshall's case).
Characters: Oliver | Dodger | Fagin | Tito | Rita | Francis | Einstein | Georgette | Jenny Foxworth | Winston | Penny (deleted) | Rufus (deleted) | Bill Sykes | Roscoe & DeSoto | Oliver's Old Kitten Friends | Louie the Hot Dog Man | Alley dogs