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I never forget about you and Moe, Harry. I always have plenty for you to do. Here.
~ Castelo giving Harry and Moe their assignment.
Brilliant. Brilliant! You killed my best waiter and you let them get away! All bets are off. Find them and kill them. Now get outta here!
~ Castelo scolding his men after they failed to kill Harry and Moe and accidentally killed his waiter, Marco.

Anthony Castelo is the main antagonist of the 1986 comedy crime film, Wise Guys. He is the Italian mafia leader of a gang of mobsters and thugs operating in Newark, namely, Frank "Frankie the Fixer" Acavano (his top man), Santo Ravallo, Joey "New Shoes" Siclione, Louie Fontucci, and his formerly less-than-appreciated and respected members: Harry Valentini and Morris "Moe" L. Dickstein. He is known for smuggling cigarettes in a warehouse he owns. He also works part-time as an Italian restaurant owner as part of his cover probably.

He was portrayed by Dan Hedaya who also portrayed Arius in Commando, Tully Alford in The Addams Family, and Brian Torelli in Law & Order.

Personality[]

As a crime boss, Tony Castelo can be very intimidating, stubborn, sadistic, merciless, bloodthirsty, deceitful, opportunistic, selfish, mean, aggressive, strict, arrogant, ruthless, cruel, and sarcastic. He takes great pleasure in mistreating and disrespecting his reluctant members: Harry and Moe by having them do his lowest jobs most of the time; much to the amusement of his other gang members. He can be very temperamental when he doesn't get exactly what he wants or when his thugs mess up big time.

Beneath his businesslike exterior, Tony Castelo can be impatient, threatening, and easily offended/insulted when he learns that Harry and Moe tried to rip him off in a rigged horse race and therefore, threatens to either kill them or their families after submitting them to different types of torture. Even if and when Harry and Moe eventually come up with the money they owe him, he intends to have them killed either way.

Biography[]

Prior to the events of the movie, Anthony "Tony" Castelo was a member of an Italian gang of mobsters and thugs operating in Newark under the leadership of Michael "Mike" Valentini. Once Valentini had retired and spent the rest of his days with his wife, Sadie and his mother, Angelina in Atlantic City as a recluse, he left Castelo in charge as the new leader of the gang including his only nephew (whom he couldn't stand sometimes), Harry Valentini and the latter's Jewish best friend and next-door neighbor, Morris "Moe" L. Dickstein (whom he couldn't stand sometimes as well), both of whom Castelo and the rest of his gang constantly mistreated and disrespected, thus, making them more unappreciated, reluctant gang members doing his lowest jobs most of the time.

One day, at his own restaurant, after prompting his men to routinely spark their lighters for him when trying to smoke a cigarette, Castelo hurriedly goes over his schedule with each member of his gang: Frank "Frankie the Fixer" Acavano (his top man), Santo Ravallo, Joey "New Shoes" Siclione, and Louie Fontucci before focusing his attention on Harry and Moe since he wants to go home and change afterwards. As it turns out, Castelo puts the last two in charge of buying his groceries and picking up his clothes at the dry cleaners; much to the amusement of the other gang members. However, seeing that Moe's jacket size matches his own, Castelo decides to have the latter try out his new jacket before shooting at him to check if the jacket is really a hundred percent bulletproof or not while Harry is reluctantly forced by Frankie the Fixer to stand and watch in silence. Satisfied with the results, Castelo orders a dozen of different colors before sarcastically thanking Moe for the test and asking Harry to start up his car to check if it's been rigged with a bomb possibly planted by either a rival crime family or the cops.

Then, Castelo sends both Harry, Moe, and Frankie the Fixer down to Meadowlands Racetrack to place $10,000 on a bet on his behalf. Knowing that their boss usually bets on the wrong horse, Harry has Moe change horses at the last minute, thinking this could be their one chance to finally fulfill their lifelong dream of opening up the world's first Jewish-Italian delicatessen. However, this time, Castelo had actually fixed the race; thanks to Frankie the Fixer, meaning that Harry and Moe now owe their boss exactly $250,000. Shocked with the results, Castelo has his men put both Harry and Moe through different types of torture each at night. Castelo tries to get information from Harry when drowning him inside a lobster tank while Frankie the Fixer tries to get information from Moe when hanging him above a pit of 4 vicious Rottweilers. However, thinking that each of these "wise guys" is lying to him in order to protect each other by not ratting each other out and proving themselves more loyal to each other than to him, Castelo decides to put them through the test by having them kill each other under false pretenses of forgiving them; especially, Harry since he is the nephew of the gang's original yet retired leader, Mike Valentini who made Castelo the man that he is today while threatening to kill either Harry's wife, Wanda and son, Harry Jr. or Moe's mother, Lil should either one refuse.

Nevertheless, the next day, when both Harry and Moe can't bring themselves to killing each other, Castelo is furious to learn that not only did his men: Frankie the Fixer, Santo, and New Shoes allow them to get away in Frankie the Fixer's beloved Cadillac, but that they also unintentionally killed his best waiter and Harry's cousin, Marco who tried to snitch on him by warning and tipping them off about the contract on each other's lives at a church. Then, Castelo orders them to call off all bets and to find and kill them. In the meantime, Harry and Moe manage to call up their own families and have them travel to Jamaica temporarily in order to save them from Castelo's wrath.

Later, Castelo learns from an informant that Harry and Moe are in Atlantic City, having checked into the superstar suite of the Resorts International Hotel Casino owned by their old friend, Bobby DiLea using Frankie the Fixer's credit cards while hoping they can find and talk to Harry's Uncle Mike about straightening things out with Castelo. So, once again, Castelo sends out Frankie the Fixer, Santo, and New Shoes to find and kill them. Unfortunately, it is later revealed that Mike Valentini has actually been dead for almost a year now at the age of 68 since all that's left of him are his ashes now (having requested that his mother and wife keep his death a secret from everyone else including his own family just the way he wants it); much to Harry's shock and Moe's disgust.

Despite Harry's grandmother/Mike's mother helping Harry by giving him the exact amount of money he owes Castelo (taken from an excessively large collection of presumably earned or stolen cash secretly saved and stashed under a bed by Mike Valentini and his family before his untimely death including Harry's $12,000 inheritance left to him by his uncle) and DiLea agreeing to help Harry and Moe sort things out with Castelo, Harry notices Castelo's men waiting for them and decides to stay behind and gamble the money, realizing that even though Castelo had promised to forgive them once paid, he was intending to have them killed either way with the help of a supposedly double-crossing DiLea. After a chase through the hotel casino, Moe catches up to Harry and accidentally shoots him. Harry is pronounced dead and Moe flees.

3 days later, Castelo and his men including Louie attend Harry's funeral. When Castelo is informed by Frankie the Fixer (eating a sandwich) that Moe is at the funeral as well, Castelo decides to let him go home and get comfortable before killing him. After the funeral, Castelo tries to offer his condolences and services to the grieving family, only to be reprimanded by Harry's widow, spat in the face and insulted by Harry's grandmother, and somewhat complimented by Harry's Aunt Sadie. Then, Castelo and his men make their way to Moe's house and break in to kill him, only to find it empty, unaware that both Moe and Harry (who actually faked his death with DiLea's help the whole time) have already left after leaving a skeleton for Moe and writing a suicide note before turning on the gas and setting fire to the curtains to make it look like Moe had actually committed suicide rather than faced death in the hands of his former boss and associates even though the door slams shut and puts the fire out. Castelo has his men search the place, but all they can find is the skeleton and an unusual smell. Then, Castelo takes out a cigarette, prompting his stooges to routinely spark their lighters for him again. However, when Frankie the Fixer asks: "Who farted?", Castelo realizes at the very last minute that the house is actually filled with gas just before it explodes, thus, killing both him and his men in it.

With Castelo and some of his men dead, Harry and Moe are now free to make an investment in the $250,000 and open up their very own Jewish-Italian delicatessen within DiLea's hotel in Atlantic City with their families tagging along, thus, fulfilling their lifelong dream at long last.

Quotes[]

Wow. The jacket actually is bulletproof. Order me a dozen. Uh, different colors. Thanks, Moe. Harry? Start the car.
~ Castelo sarcastically thanking Moe after helping him test his new bulletproof jacket and before asking Harry to start his car.
Friendship, Harry, goes out the window at these moments. I've seen it happen time and time again. What I want now is clarity. Whose idea was it to rip me off? To steal food from the mouths of my wife and children?
~ Castelo torturing Harry.
Castelo: This, I didn't expect. I figured Valentini would sell the Jew down the river, but this is interesting. They're protecting each other.
Frankie the Fixer: Let me waste them, Mr. Castelo.
Castelo: Do we really hurt them by killing them?
Louie: It's a good start.
Castelo: But have we taught them anything? No. The real issue here is loyalty. I wanna know why these wise guys are loyal to each other and not to me. So, let's put them to the test.
Frankie the Fixer: Like how?
Castelo: Like having them kill each other.
~ Castelo planning to have Harry and Moe kill each other as a test of loyalty.
Take it... and kill Dickstein.
~ Castelo ordering Harry to kill Moe in exchange for the latter's family's lives.
One down, one to go. Let him get home, get comfortable. And then,...
~ Castelo intending to kill Moe after Harry's funeral.

Trivia[]

  • Despite Harry's family relationship to his former boss, Mike Valentini who started him in the crime business, Castelo shows the least bit of respect for both him and his best friend, Moe, which may imply that he neither really showed real respect for his former boss nor did he really care about the consequences that might've befallen him had Mike Valentini known about the situation and had he still been alive for that matter even though he could never really stand both Harry and Moe much sometimes and even when it came to threatening to kill both Harry's wife and son and Moe's mother as well.
    • Despite Marco being Harry's cousin who eventually betrayed him when trying to warn and tip both Harry and Moe off about the contract on each of their lives, Castelo still seemed to show admiration, respect, and care for Marco mainly, as demonstrated when scolding his men for both accidentally killing Marco whom he refers to as his best waiter and letting his two former associates escape death. Same for Harry's grandmother, Angelina despite her insults and Aunt Sadie.
  • When going over his schedule with his thugs, Castelo mentions bribing a judge and a police chief, which probably explains why he has never been apprehended by the law so far.
    • Castelo also mentions a shipment of cigarettes whereas one of his thugs, New Shoes mentions a warehouse, thus, implying that Castelo also operates as a cigarette smuggler and a warehouse owner.
  • According to Moe, Castelo is also in the olive oil business. Whether that's partially true or not remains unknown.
  • Given his history of having his cars explode, as demonstrated in one scene when Harry was assigned by Castelo to test his car, it is possible that Castelo has a longtime rivalry with either another crime family operating in Newark or simply cops trying to do away with him as soon as possible.
  • While torturing Harry, Castelo mentions his wife and children, thus, implying that he might be possibly married with children.
  • After Castelo and some of his men have been killed at the end, it is unknown what happened to the other unnamed members of his gang (including one named Georgie in an earlier scene). Either they eventually got arrested for their crimes or escaped custody.
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