In mid-July 1999, Al was in the midst of a feud with Droz. Droz's ally, Prince Albert, destroyed Al's mannequin head (coincidentily referred to as, "Head") after the match. On the July 19th RAW episode, Al, the current WWF Hardcore Champion, was scheduled to defend his title against the Big Boss Man. He came to the ring, carrying a bandaged-up Head. Before the match even began, Al stepped into the ring and begged Boss Man to hit him with his trademark nightstick, a challenge that Boss Man happily obliged to, DQ'ing himself before the match even began. Boss Man eventually handcuffed Snow to the ring turnbuckle, and proceeded to knock him silly, repeatedly bashing him with the nightstick. Snow retained his title due to the face that championships can't change hands on DQ finishes. A Hardcore Title Match was instantly booked between the two at the Fully Loaded Pay-Per-View.

The match began with the two fighting at the entranceway, as Snow didn't even allow Boss Man to get halfway to the ring before attacking him. Boss (as I'll refer to him from now on) quickly gained the advantage, once again demolishing Snow with his nightstick. They began brawling into the crowd, where Boss found a chest, and stuffed the challenger inside. He backed up a few steps and grabbed his nightstick, but Snow quickly climbed out of the chest and hit Boss with a sandbag. Snow went for an Irish Whip, but was reversed into a ringside lighting set. The fight began to move into the backstage area. Cardboard boxes (?), streetsigns, and a small metal bar were all used. Al soon regained an advantage, bashing Boss with a cookie sheet, and pouring hot cofee on him. Al sloppily suplexed Boss through a table. Boss got up soon after, and grabbed a football-down marker and hit Snow with it. It barely affects Snow, so Boss Man tries to wheel himself away in a shopping cart, but it won't go. A frustrated Boss climbs out, but Al hits him with a nearby plant. Boss then whips Snow with the Hardcore Title belt. The match moves to the parking lot, where Boss bulldogs Snow on the concrete sidewalk, but kickout of the pin. Snow nailed his opponent with a car hubcap, only to get his present returned to him with a brick getting bashed into his head. They brawl into a crowded street full of cars, where one almost runs them down!!! Boss bangs Snow's head into some stop signs and a fence. Snow is handcuffed to the fence, and Boss repeatedly bashes him with a steel rod. Boss then pinned Snow for the 1-2-3 count and the Hardcore Title win.

Over the next few weeks, the two rivals interfered in eachother's matches, costing them some wins. Snow adopted a pet chilhahua (CHI-WAW-WAH), and named it, "Pepper," in a pecuiliar series of events. A Hardcore Title Rematch was booked between Snow and Boss at SummerSlam, and that match would go down as possibly the greatest WWF Hardcore Match of all-time. Road Dogg had challenged the winner prior to the match to a Hardcore Title Match the next night on RAW, so he did guest-commentary on the micropone, following the participants around wherever they went.

It started out with Snow climbing up onto a balcony, and, as Boss entered with his Hardcore Title, leaping off onto the defending champion. The match eventually went to the backstage area, where Boss gained the advantage, naiing Snow with anything in sight, including a crutch, a steel chair, and tossed him into the wall a few times. He then used a chalkboard to nail Snow with, and even a dog cage. Snow gained the advantage and broke the chalkboard over Boss's head. Boss used the crutch on him, and tossed Snow into a soda machine. Snow then tossed Snow into the soda machine again, and then a car window, that was parked backstage. They each were tossed into a garage door located backstage, before it was lifted, and they brawled to the outside. Snow was tossed into a guardrail, before they brawled into the street, and Snow's then thrown into some construction equipment in the middle of the street. They fight on the sidewalk across the street, and Boss kicks out of a pin. Snow's tossed into a ton of plastic tables and chairs, but kicks out of the pin. They fight into a bar, where a fan on a cell phone gets right into the face of the camera, causing Teddy Long to yell at him to "Get out'a the way," and Jim Dotson to restrain the fan. Anyway, Boss gets repeatedly hit by Snow, who the fans in the bar are solidly behind, repeatedly chanting, "Head!". He uses various weapons, until Boss gains the advantage. They use broomsticks on eachother, before fighting into the men's bathroom. Boss's face is shoved into the urine-toilets. They finally brawl back into the main lobby of the bar, where Snow tosses a beer bottle at Boss, and chokes him with a chain. All the while, Road Dogg's still doing commentary. He moonsaults off of the barroom counter and puts Boss through a table. They fight into the pool-room, where Boss pushes Road Dogg to get out of the way, causing the 'Dogg to retalliate, and use Boss' own nightstick on the Boss, allowing Snow to put the exclamation point on Boss when he uses. He pins him on top of the pool-table, pinning him for the three-count and the Hardcore Title. He then runs back across the street and into the arena.

Snow was the new WWF Hardcore Champion, but his toughest battle was still ahead of him. The next on RAW, it was announced that Boss Man had stole Snow's pet dog, Pepper. Snow came out to the entranceway to confront Boss Man, who was conducting a promo. He told him he wanted Pepper back. Boss Man said that he'd give Pepper back under only one condition: if he got a Hardcore Title rematch. Snow agrees, but, at the same time, makes it clear that Boss Man better not touch Pepper. Later that night, Boss Man gets his title shot. He enters the ring, along with Pepper. Boss Man wins the match and the Hardcore Title with a nightstick-shot, but he leaves the ring and goes backstage along with Pepper. A weeks after, Boss Man says that he'll give Snow Pepper back if he comes his hotel room.

Snow, the cuckoo that he is, complies and goes to Boss Man's hotel room on SmackDown!. Boss Man offers Snow some Fajitas while he goes to get Pepper, who's supposedly being groomed, from the other room. Snow, once again, complies. Boss Man comes back without Pepper, and tells Snow to "Try not to get of them paws" stuck in his teeth. The realization suddenly sinks in to Snow and the fans watching. Snow then begins to get ready to hurl, as we go back to live action. The next week on SmackDown!, Sgt. Slaughter referees a "Pepper On A Pole Match" between Snow and Boss Man, with the winner being the man who climbs the pole and grabs Pepper's remains. During the match, British Bulldog accompanies a bunch of rottweilers to ringside, who chase Boss Man away to the backstage area, allowing Snow to grab Pepper's remains. The first-ever "Kennel from Hell Match" is made between the two at Unforgiven for the Hardcore Title. A week or so later, the Bulldog and the Boss Man fight for the Hardcore Title. Bulldog won the match, and the title, but Snow came out to get even with Boss Man. However, before he got to Boss Man, Bulldog came up to him, and gave him the Hardcore Title. Al Snow was officially the new Hardcore Champion.

The match takes place in a Steel Cage, which within a Hell in the Cell structure. Between the Steel Cage and Hell in the Cell are a bunch of rottweilers. The goal is to escape both cages (over the Steel Cage and through the cell door), and the man to do that first will become the Hardcore Champion. The match was a real joke, with the storyline that Snow was out for revenge on Boss for cooking his dog. Anyway, the fans were still into it, and the dogs provided a laugh. It was a pretty bloody match for both men, with a shovel, wire-cutters, and Boss' nightstick being used. In the end, Snow nailed Boss with Head, giving him enough time to escape both structures, avoiding the dogs and grabbing the Hardcore Title and running to the backstage area. Snow had retained his Hardcore Title from his arch-nemesis.

That was the end of the Al Snow/Big Boss Man feud. Like the Snow/Bob "Hardcore" Holly, it was mainly used for entertainment, but it did provide fans with some great matches. After all, how often do you get to see two grapplers brawling in the middle of the street and in a bar, with one of them moonsaulting through a table? Get the point? Yeah...