Benny was a member of the tribal gang called the Boot Riders before Mr. House took over Vegas. As one of the three tribes who agreed to House's new rule, the Boot Riders were assigned to renovate The Tops casino. They were given suits and ties and renamed "The Chairmen." Benny saw the potential of New Vegas, but the tribe's chief at the time, Bingo, wanted to stay nomadic. To determine the direction of the tribe, Bingo challenged Benny to a knife fight, and the winner would be the leader of the tribe. Benny stabbed Bingo in the throat, killing him and winning the fight. Benny is quick to stamp out dissent among those Chairmen who support the old ways, even killing an old friend, an unnamed singer with a Psycho overdose.
Benny's long-term goal is simple: to control New Vegas. The chances of such a thing happening seem very slim, but as Benny himself would say, he's not done rigging the odds yet. After attacking one of Mr. House's PDQ-88b Securitrons with a pulse grenade, Benny brought it in for examination. Unable to fix it himself, he allowed Emily Ortal to inspect it in exchange for her reprogramming it. After finishing the reprogramming, the Securitron became known as Yes Man, an AI designed to obey every command given to him. Benny used Yes Man's compliant nature to interrogate him on the details of House's machinations.
He learned Mr. House had something buried underneath The Fort and of the platinum chip—the key to all of House's plans. He also learned of the seven couriers hired by Victor—six decoys, and one carrying the chip. Using Yes Man, Benny was able to discover the route the Courier would take, and hired Jessup, McMurphy and Chance to help him finish the job. The Courier was bound, gagged, shot in the head, buried in an unmarked grave at Goodsprings Cemetery, and left for dead.
After betraying his Great Khan accomplices, Benny made his way to The Tops and stays in the casino area with four loyal bodyguards. However, unbeknownst to Benny, his actions haven't been unnoticed by Mr. House.
They Went That-a-Way: The Courier tracks Benny in an attempt to discover the purpose of the package and get revenge. Manny Vargas is the first person to give the player Benny's name, and where he went. Jessup in Boulder City will reveal that Benny betrayed his Great Khan partners after intercepting the Courier, traveling to New Vegas and leaving them to fend for themselves when cornered by the NCR.
The House Always Wins: House wants the platinum chip back in his possession. He needs you to recover it from Benny.
Ring-a-Ding-Ding!: The player must confront Benny at The Tops casino, which results either in Benny's death, or him escaping to Fortification Hill with the platinum chip in an attempt to activate House's secret weapon, where he gets captured by Caesar.
Render Unto Caesar: Benny is captured by Caesar, who offers the Courier a gift by allowing the Courier to choose how Benny dies. Benny, for his part, seems accepting of his impending death, and urges the Courier to take over his plan and create a truly independent New Vegas. Benny can be killed outright, be made to fight the Courier one-on-one inside the Arena, or be crucified by the Legion (only the latter fate causes Benny to panic in any way, given its incredibly painful and torturous nature). Benny can also be untied by the Courier, at which point he will flee Caesar's tent and disappear from the game. Sparing Benny will cause Caesar and his praetorian guard to become hostile, leading to a very difficult fight. If you kill Benny (when he is tied up in the tent) before you take the quest, Caesar and his guards will become hostile towards you. You also have the ability to free Benny from captivity by giving him a stealth-boy and a bobby pin. However, this will result in the Legion turning hostile towards you.
If the Courier is a female with the Black Widow perk, you can convince Benny to take you to his room, where you can either attack him or sleep with him. After some humorous dialogue, you are given the option to kill him quietly in his sleep or leave him be. If you choose the second option he will instantly teleport to Caesar's tent, disallowing you to kill him on the Strip.
An event would have Benny meeting the Courier again after being freed from the Fort. In the event Benny would have equipped a Stealth Boy in order to sneak up on the Courier, and initiate dialogue in which he would mock him/her for showing him mercy and after that go into attack mode, which would most likely cause him to be killed by the Courier. This event was cut from the final game.
If you sleep with him and don't kill him in his sleep, he will leave a note thanking you and saying not to follow him to The Fort, and it also says that when he gets back, the Courier and Benny would go on a date.
If you are a female character with the Black Widow perk and sleep with him and then free him from the Fort, he does not keep his promise of a date, as he disappears from the game after exiting the area.
If you kill everyone in the Fort while Benny is still tied up, he will say "You're a scrapper, baby, they didn't stand a chance," then you will receive the option of freeing him, leaving him, or killing him once you finish dialogue.
After killing him, he will usually only have a single 9mm round on his corpse.
One of the challenges in Gun Runners' Arsenal ("Talk About Owned"), requires you to kill Benny with his own pistol, Maria.
Benny becomes a superfluous character in the NCR quest line, and should the player pursue an NCR victory and never interact with Benny upon entering the Strip, he can survive until the end of the game.
When the Courier steals from him and Benny sees it, there will be no Karma loss. In addition, he may mutter "That don'tIn-game spelling, punctuation and/or grammar belong to you!"
In the opening cutscene, Benny looks the Courier in the face and says "The truth is, the game was rigged from the start" before shooting them in the head. In doing so, Benny is subtly talking not to the Courier themself, but instead to the person playing the Courier. This is known as breaking the fouth wall, a term which originated in box set theatres, which entailed that there was an imaginary wall separating actors from the audience, which prevented actors from interacting with the audience and vise versa. However, some plays involve stage actors talking to or even engaging the audience. This concept has begun to be applied metaphorically to other forms of fiction, including video games.
A Benny is a trump card in trick-taking games, essentially a wild card, and is often represented by the Joker, Benny's card in the Collector's Edition deck.
At one point in development, the Chairmen were going to be called the Geckos, with Benny as the head of the Gecko family. However, this name was dropped from development and thus didn't make it into the retail-release of the game.
Benny is a reference to Benjamin "Bugsy" Siegel, who is often thought of as the father of modern-day Las Vegas. The similarities exist in the name and in Bugsy's trademark suit, which bears a striking similarity to Benny's, along with the fact that the two are very similar looking.
pcxbox360ps3 If you choose to crucify Benny, he will end up being crucified outside of The Fort. Sometimes, both the crucified and regular versions of Benny will appear, and the regular version can be killed for Maria. Yet you will not receive Maria twice it will only be on the Benny that is standing up next to the cross. Talking to Benny next to the cross will result in you deciding to kill him again. [verified]
ps3xbox360 If the player kills Benny before talking to him in his casino without getting noticed, the guards will continue to stand in their positions as if they were still protecting him. [verified]
xbox360 If while in Caesar's tent when Benny is kneeling, you perform Ranger Takedown Benny will be knocked from his position on the floor, stand up and protest. Caesar and his guards will not protest or react even though "Benny is forbidden to speak under penalty of death," until you kill him, at which time one of the guards may praise the PC's fighting prowess immediately before attacking the The Courier. [verified]
pcxbox360 If the player has the Super Slam! perk, Ranger Takedown perk or a weapon that inflicts fatigue damage, it is possible to knock Benny off his cross. Upon landing, he will continue to act as if on the cross, but he will be standing on the ground. The same also happens when Benny is in Caesar's tent kneeling. [verified]
xbox360 If you choose to crucify Benny and kill him while he is crucified he can re-spawn if you kill Caesar and you can let him down for Karma he will have his suit on but he will not have Maria. [verified]
xbox360 If you have Benny come up to the presidential suite with you, and let him survive, he will move to the front of The Tops lobby. If you have 35 barter skill, you can then repeatedly choose (what do you have in mind?) and (The suite's a nice touch...), which will give you 500 caps and 250 The Tops chips every time. This bug allows for effectively infinite money. [verified]
pc When you talk to Benny at the first time in The Tops Casino, stand up in front of him and let him survive, and you can repeatedly choose the option dialogs between speech and barter skill. Speech will give you 60XP, and Barter will give you 500 caps, 250 The Tops chips and 35XP. This allows you get infinite XP and money and raise your level. [verified]
pcxbox360 Sometimes after you talk to him in his suite, his bodyguards will not come in and attack you, but if you rescued him from The Fort and talk to him back in his suite, after ending the conversation he will get up, walk out of the door and his guards will enter the suite. This bug also makes him disappear from the game completely. [verified]
xbox360 Sometimes the Maria can't be pickpocketed from him while in Caesar's Tent. This can be fixed by placing a live explosive in his inventory, and after that taking all contents ("Take all"). Optionally, you can select the Maria before Benny explodes. This way you can get the Talk About Owned challenge. [verified]