A character straight out of the Prohibition Era, Buttons McBoomBoom is a cold faced, serious looking hitman who serves Big Boss as his personal bodyguard. He is seen wearing a red suit and fedora and carries around a violin case that hides his favorite playtoy, a deadly modified Thompson submachine gun with a scope attachment that he uses to blast away at any target at will. He talks coldly. Even in the comics, you can see he talks in a very cold manner by looking at his stylized word balloons that appear to be dripping with melting ice. Buttons McBoomBoom hides, underneath his suit, a cybernetic torso that bears twin machine guns with which he blasts away after he unbuttons his shirt to reveal them in the heat of battle against either the C.O.P.S. or a bug.
Buttons McBoomBoom hates bugs and expresses this in a hostile way when he tries to take on the Bugman's army of bugs in The Case of the Baffling Bugman, where he obviously developed a sheer hatred of bugs from, and The Case of the Stashed Cash where he tries to blasts away at a "crummy fly" that's annoying him at the penthouse poolside, when he was surrounded by a bunch of moths when he crashed into a stack of old clothing at the abandoned West Side Laundry, a place that once served as a hideout for Suds Sparko, and lastly in the opening intro when he takes on a butterfly shown to actually be its shadow he's firing at as Nightshade tries to rob a wardrobe filled with jewels.
In the comics, McBoomBoom has a twisted philosophy that involves not killing anyone. Instead, he just lets his target live after he breaks them down. He displays this philosophy when he went after LongArm's family in The Long Cuff of the Law and Bulletproof in Buttons on a Vess later on.
In this episode, McBoomBoom got upset when he lost his lucky penny: the very first penny he ever stole. He searched frantically for it in the sewers and also in his old rundown apartment house. Big Boss wanted him to rob the lottery machine filled with money at a huge mall but Buttons can't find his lucky penny and he's been getting a lot of bad luck as a result of this. Big Boss, to get Buttons to do the heist, decides to "substitute" the coin with a fake one and says to Buttons that he found the real lucky penny he's been looking for. McBoomBoom, ecstatic over this, wanted to kiss him, but Big Boss didn't want that kind of reward. McBoomBoom begs Big Boss to give him the coin. Big Boss agreed, on the condition that he go and rob the lottery machine at the mall.
McBoomBoom agreed. So, he took Turbo Tu-Tone and went out to rob the mall. He found out later that while holding onto some helium balloons that floated him up in the air to escape the C.O.P.S., that he had been double-crossed by his own boss.... and he was going to kiss him! All because Big Boss gave him only a worthless counterfeit coin instead of the real lucky penny that is now at the hands of Brian O'Malley, Longarm's son, who found the coin and exclaims, "Gee, it must be my lucky day!"
In The Case of the Crime Convention, Buttons and Berserko, both while attending The Annual Crooks Convention, finds out that Big Boss plans to present the Criminal of the Year Blackjack Trophy Award to one lucky crook tomorrow. Each determined to achieve that title, both Buttons and Berserko wastes no time in trying to outdo each other. The next morning, as Berserko was pulling a robbery at a bank, across the street, Buttons was also pulling a robbery from another bank as well. Both crashed into each other as they took off to escape with a bag of loot over their shoulder. Just as they were about to fight it out, they heard sirens blaring as the Hardtop and Mainframe speeds off to the scene of the crime. The 2 crooks had to run off, leaving the stolen loot behind.
Later, Buttons sought Dr. BadVibes' advice on how to commit the biggest crime in Empire City in order to win the Criminal of the Year Award. After getting some ideas, He then, went to the C.O.P.S. precinct and stole Hardtop's Ironsides vehicle and ran off with it. Hardtop, seeing the Ironsides speeding off with Buttons inside, went after it with his other vehicle, a sports car from the 1990s'. Along the way, Buttons had to stop and look with scorn over the large campaign posters of Berserko laughing with inscriptions shown on the top and bottom of the photo that reads "Berserko for Criminal of the Year." Buttons ranted a bit before taking off again in the stolen Ironsides after he hears Hardtop coming towards him. Buttons eludes Hardtop, but lost control a moment later and fell off the expressway bridge and fell many feet to the ground, destroying the vehicle. Luckily Buttons wasn't hurt much and he is able to escape.
Later, Buttons learned that Berserko and Rock Krusher plans to change the appearance of a large statue adorning the main outdoor area of City Hall into a statue made into the image of Berserko. Buttons, in an attempt to get him out of the way by having him arrested and eliminate him from the competition, hides his identity with his fedora and informs Mainframe on the video phone about what's going on at City Hall. With the Ironsides repaired, Hardtop and Mainframe speeds to city hall and proceeds to apprehend Berserko and Krusher. But Berserko dumped a lot of quick-drying cement on the 2 C.O.P.S., embedding their feet inside it so they can't move at all. Then, he took them to the convention center where they were used as a special display being put on for all the crooks to marvel at.
But as the convention meeting went on, Mainframe and Hardtop, with their feet still stuck in the cement, simultaneously stomp their way out of the center, knocking down anyone that got in their way. They managed to stomp their way from the building and across the road to a nearby phone booth, where they called up headquarters and request assistance in breaking up the convention and freeing her and Hardtop from their predicament. Bulletproof wastes no time in leading his team out the door and into their vehicles where they speed off to rescue Mainframe and Hardtop and break up the meeting.
Meanwhile, Big Boss was about ready to give out the Criminal of the Year Award when the C.O.P.S. team arrived at the Center with Mainframe and Hardtop waiting for them at the building's entrance. As they prepare to enter inside to take on the crooks, Big Boss announces the winner of the award,
Big Boss: "And the winner is...ME!"
Shocked over the result, Buttons and Berserko protest. Nevertheless, just as Big Boss was giving out his acceptance speech, the C.O.P.S. team suddenly appears to place everyone in the auditorium under arrest. They were able to apprehend all of the crooks in the room, except Big Boss, BadVibes, Buttons, and Berserko who all got away, leaving the blackjack trophy behind.