Not much is known about his background other than the fact that he's a criminal and never made it past the sixth grade. As for weapons, he has a crow bar (like Marv) which he uses to break into Kevin's house and a gun which becomes useless when it's filled with paint varnish from Kevin's booby traps. So, he never uses it and it's supposedly taken away by the police. In the second film, Harry still has the "M" from the McCallister doorknob branded on his hand from when he touched it not knowing that Kevin had heated it up.
In the first film, Harry is one of the Wet Bandits along with his partner Marv who plan on robbing the McCallister's home while they're on vacation in Paris, France. In the beginning of the first film, Harry is seen in disguised as police officer uniform and goes into the McCallister home as a cop and tries to find out when the McCallister's are leaving for their trip but when he tries to get someone's attention everyone is too busy planning to leave for their trip.
When the pizza boy comes to deliver the pizza Harry opens the door for him and the pizza boy tries to give him the pizza but Harry rejects that it's not for him. The pizza boy then asks him if he's just around for the holidays to which Harry replies "I guess you could say that". Harry finally manages to get Peter McCallister's attention and informs him that the police are checking houses around the neighborhood to make sure that everyone is taking the proper precautions because there's a lot of burglaries around the holiday season and Peter tells Harry that they have locks on their doors and automatic timers for their lights. Peter then asks Harry if he wants any eggnog. Then Harry starts to ask Peter when his family will be leaving but before he can Peter is pulled into the kitchen by his oldest son Buzz to eat pizza.
Harry finally manages to get Kate's attention after she's done paying the pizza boy and he also smiles at her youngest son Kevin showing his gold tooth. Kate tells Harry that her brother-in-law Rob transferred to Paris last summer and that he's giving the whole family a free trip to Paris to spend time together on Christmas and that they plan to leave first thing in the morning, to which Harry replies "Excellent." Kate then asks him to excuse her so she can take her son Kevin upstairs but Harry tells her that it's okay because he spoke to her husband and that her home is in good hands, then he leaves. Later on, after the McCallister's left for their trip, Harry is seen in his van with Marv on the street near Kevin's house and tells Marv that he managed to trick the people in the neighborhood into believing that he was a police officer and that they told him they were leaving. They attempt to make their first move on breaking into the house, but Kevin, having been left behind, notices their shadows walking alongside the house from the inside, and turns on all the lights. A confused Marv acknowledges to Harry that he thought Harry said the McCallisters had left already, to which Harry responds positive, saying that they were supposed to leave that morning. Not wanting to take any chances, the two burglars flee.
The next morning, the two robbers decide to rob the Murphy's house, the neighbors across the street from the McCallister's house, instead. When Peter McCallister attempts to call the Murphy house in an attempt to reach out to his son left behind, the two robbers realize that Harry was right about the McCallisters being gone, and plan to rob the house later that night. As they leave, Marv plugs up the kitchen sinks and turns it on and leaves it running. When Harry finds out that he's done it again (having done it many times before for previous robberies), disapproves of it, calling it "a sick thing to do," but Marv disagrees, calling it their calling card, believing that all the best robbers leave their mark at the scene of the crime, thus giving them their name "the wet bandits." During a brief argument over the topic, Kevin walks past their driveway as they pull out, almost hitting him before Marv notices and stops Harry right at the very second. Harry rudely tells Kevin to watch what he's doing, with Marv commenting "Santy don't pay for the funeral homes, little buddy." In an attempt to brighten things up, Harry wishes Kevin a merry Christmas and smiles at him, but Kevin, recognizing the silver tooth from when Harry was posing as a cop, sees through their disguise and realizes his house is in danger. Discomforted at how Kevin looked at him, Harry pursues him, knowing that Kevin knows something about them. As they drive up to a church, Harry, not wanting to go into a church, gives up the search. Later that night, the burglars arrive as planned, but Kevin, knowing they'd arrive, animates and dresses up mannequins and plays loud Christmas music to make it appear that the house was occupied. The burglars are confused once again and once again abandon the plan.
Coming back the next morning, Harry, sends Marv to investigate the house, knowing something is up, since the house seems completely vacant, despite the uproaring event the night before. Kevin is there once again, and plays an old gangster movie to make it seem like two criminals had already beat them to robbing the house and argued over a matter, before blasting him away with his gun (Kevin set up firecrackers in a pot in front of the door to make the effect of the gun seem more effective). A freaked out Marv tells Harry of the situation, and Harry sees it as an opportunity to turn in two outlaws to get something in return. Remaining there the whole night, as Harry awakens the next morning, he sees Kevin walking out his house to saw down a pine tree in the backyard for a Christmas tree. Recognizing Kevin, he realizes that he and Marv have been being fooled the whole time. Despite Marv's protests of a child being alone at the house, Harry still insists on going through with the robbery anyway, commenting that the house was "the only reason they started working on the block in the first place." After going through various plans with Marv, Harry concludes with them returning around 9:00. Kevin has overheard this, and sets up booby traps in the house. Going through the back door, Harry and Marv try to ease their way in by attempting to fool Kevin by pretending to be Santa Clause "and his elf" with presents for him. Kevin doesn't buy it for a second however, and shoots Harry in the testicles with a BB gun through the doggy door, Marv following getting shot between his eyes. Both enraged, the two realize what kind of kid they're dealing with, and Harry sends Marv to the basement door while he goes to the front. After going through various booby traps, such as slipping on the icy steps, getting his hand burnt on an overheated doorknob, getting his head burned with a blow torch, getting feathers and glue onto him, slipping on micro machines, getting hit with paint cans, and tripping over a wire Harry is ready to kill Kevin.
After Kevin puts Axel on Marv's face in an attempt to escape, a hysterical Marv throws Axel on Harry, crawling onto Harry's upper chest. Harry doesn't notice Axel and is only intimidated by Marv insanely attempting to hit him with a crowbar (Marv was trying to kill the tarantula), but the tarantula escapes, only enraging Harry and briefly starts whacking him with the crowbar. As they continue to pursue Kevin, Kevin flees to the Murphy's house (having called the police to get them there). However, Harry outsmarts Kevin, ambushes and catches him. Harry then plans to put Kevin through the same torturous injuries he put them through, but not before biting off all of Kevin's fingers. However, just as he is about to do so, he and Marv are knock out by Old Man Marley behind and gets Kevin home as the two bandits are arrested as the police arrive.
Home Alone 2: Lost in New YorkEdit
After having spent nine months in jail, Harry and Marv break out of jail. He and Marv stowaway on a fish truck and plan on getting ahold of false passports and hide off in "some foreign country." Marv decides to change their nickname "The Sticky Bandits" after taping his hand to stick some change to his hand. Unknowingly, Kevin bumps into Harry passing through a large group of pedestrians. Harry initially believes to recognize him, but never got a better chance to fully see him.
At an ice rink, Harry calls Marv forth, and acknowledges to him that they have to change their game, as they aren't going anywhere with stealing goods; they decide to steal cash instead. Marv suggests robbing hotels, but Harry knows that tourists aren't guaranteed to have much cash. Harry then suggests robbing a toy store, since they make the most money around Christmas time. Making it to Duncan's Toy Chest, they plan on staying there overnight, steal the money, and then leave the following morning.
Harry and Marv then realize that Kevin is also in New York after seeing the McCallister name on the back of Peter's bag when Kevin leaves Duncan's Chest. They chase him down the street but are tripped up when Kevin breaks some necklaces, stripping the pearls off. Marv and Harry later catch Kevin when he flees The Plaza Hotel when he is exposed for having a stolen credit card by the staff, and ripped Kevin's plane ticket that way he won't get back home or get to Miami with his family. Marv reveals their entire robbery plan to Kevin and their plan to kill him much to Harry's annoyance, believing he isn't a threat to their plans with Kevin recording their confession on his Talkboy. Kevin manages to flee their grasps once again when he causes both Marv and Harry to be punched by the same woman Marv had previously been slapped for hitting on earlier and escapes in the back of a horse-drawn carriage. Harry is initially discomforted knowing that Kevin is around, but Marv eases Harry's worries, as Kevin has no home to booby trap them with, and on top of that, is now alone in Central Park, which nobody can survive at night.
On Christmas night while Harry and Marv are robbing Duncan's Chest, Kevin knocks on the window, takes a photo and throws a brick through the window setting off an alarm. Marv and Harry both unknowingly jump onto a plank and trash can set up as a makeshit see-saw which sends Harry flying through the air on top of a car. Harry and Marv chase Kevin down to the roof of his uncle Rob McCallister's house as Harry attempts to trick Kevin into throwing down his camera by promising to leave Kevin alone if he agrees. Kevin doesn't go through and tricks him by throwing down bricks that miss Harry each time and hit Marv in the forehead. Harry vengefully goes around the back and warily glances at both a window and the fire escape ladder, choosing to jump onto the ladder believing the open window is a trap. Harry then slips and hurts his back due to the rungs of the ladder being soaked in a green slime as he mumbles angrily. After going through more deadly booby traps(like tools falling on his head, head getting burned with a blow torch and mistakenly dipped in kerosene, falling from a cut-up ladder), Harry and Marv chase him into the park, where Kevin has called the cops to pick them up, identifying them as the robbers of Duncan's Toy Chest. However, Kevin slips and falls, allowing Harry and Marv to catch up to him and subdue him. In the park, Harry, having enough of Kevin, attempts to shoot him and get rid of him once and for all. However, they are distracted when the pigeon lady throws bird seeds at them, attracting an entire flock of doves to pick them off allowing Kevin to escape, leaving behind the evidence of their crimes. As the police arrive to take Harry and Marv away, Harry continuously kicks at Marv for rambling to the police about their schemes.
- It is still known that Harry still has M branded on his hand in the second film when he caught Kevin.
- His name may be a reference to Orson Welles's con-man character from the radio show "The Adventures of Harry Lime", who also appears in the film The Third Man (1949).
- According to the Internet Movie Firearm Database, Harry is carrying what appears to be a Smith & Wesson Model 10 Revolver - .38 Special while disguised as a cop. http://www.imfdb.org/wiki/Home_Alone#Smith_.26_Wesson_Model_10_Revolver
- Harry is an unseen character in Home Alone 4 (which shares a loose continuity with the original two films), having been ditched by Marv. See Harry Lime (Home Alone 4).