Benny

Benny is the head of the Chairmen of New Vegas in 2281. He is the brains behind a complex scheme to usurp control of New Vegas from Mr. House and serves as a secondary antagonist in Fallout: New Vegas.

Background
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 seemed very slim, but as Benny himself would say, he was not done rigging the odds yet. After disabling 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 stayed in the casino area with four loyal bodyguards. However, unbeknownst to Benny, the Courier was not dead... and his actions had not gone unnoticed by Mr. House either.

Quests

 * 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 character Benny's name and where he went. Jessup in the Boulder City ruins 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 the Courier to recover it from Benny.
 * Ring-a-Ding-Ding!: The player character must confront Benny at the Tops casino, which results in either Benny's death, or him escaping to Fortification Hill with the platinum chip in an attempt to activate House's secret weapon, where he is 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, the Courier will gain negative Karma by doing this). 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 the Courier kills Benny (when he is tied up in the tent) before they take the quest, Caesar and his guards will also become hostile. The Courier can free Benny from captivity by giving him a Stealth Boy and a bobby pin. However, this will also result in the Legion turning hostile.

Other interactions
If the Courier is a female with the Black Widow perk, they can convince Benny to take them to his room, where they can either attack him or sleep with him. After some humorous dialogue, they are given the option to kill him quietly in his sleep or leave him be. If the Courier chooses the second option, Benny will instantly teleport to Caesar's tent, making it impossible for the Courier to kill him on the Strip.

Appearances
Benny appears only in Fallout: New Vegas and All Roads.

Behind the scenes

 * A "Benny" is a trump card in trick-taking games, essentially a wild card, and is often represented by the Joker, which is 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 did not make it into the retail-release of the game.
 * Benny's voice actor, Matthew Perry, is best known for his decade long role as Chandler Bing on the hit 1990s situation comedy Friends. Benny himself bears a striking resemblance to Perry.
 * Benny's appearance 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 and appearance, which resembles Benny's.

Bugs

 * If one chooses 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. One cannot 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.
 * If one 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.
 * If while in Caesar's tent when Benny is kneeling, one performs 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 he is killed, at which time one of the guards may praise the player character's fighting prowess immediately before attacking the Courier.
 * If one 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.
 * If one chooses to crucify Benny and kill him while he is crucified he can re-spawn if the player character kills Caesar and they can let him down for Karma he will have his suit on but he will not have Maria.
 * If the player character has Benny come up to the presidential suite with them, and lets him survive, he will move to the front of The Tops lobby. With a barter skill of 35, one can then repeatedly choose (what do you have in mind?) and (The suite's a nice touch...), which will provide 500 caps and 250 The Tops chips every time. This bug allows for effectively infinite money.
 * Upon talking to Benny for the first time in The Tops Casino, by standing up in front of him and letting him survive, one can repeatedly choose the option dialogues between speech and barter skill. Speech will award 60XP, and Barter will provide 500 caps, 250 The Tops chips and 35XP. This allows one to get infinite XP and money.
 * Sometimes after talking to him in his suite, his bodyguards will not come in and attack, but if one rescued him from the Fort and talked 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.
 * Sometimes the Maria cannot 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, one can select the Maria before Benny explodes. This way one can get the Talk About Owned challenge.