Ring-a-Ding-Ding!

Ring-a-Ding-Ding! is a main quest in Fallout: New Vegas.

Quick Walkthrough
OR OR OR
 * Speak to Swank at the reception desk when first entering The Tops Casino. Having a combination of 3 Speech checks/bits of evidence Swank will distract Benny and let you search his room for evidence.
 * Speak to Benny directly.
 * He'll ask the Courier to wait in a presidential suite, and then flee; his bodyguards will be waiting in an ambush at the suite. However, if you use the intercom upon entering the suite, you will engage in dialogue where you have the opportunity to complete 2 speech checks, which results in no assassins being sent up to the suite. Alternatively, you don't have to actually go to the suite; promptly leaving the casino will trigger dialogue that finishes the quest.
 * Passing a speech check of 60 convinces him to go alone with the courier to the suite where he'll answer questions before attempting to make a deal with the Courier.
 * Using the Black Widow perk will grant addition dialogue choices that will convince Benny to go up to his suite alone with the Courier and have sex and kill him in his sleep, or attack when alone.
 * Confront Benny physically on the Main Floor. This will turn the whole casino hostile unless you've received Swank's help (two speech checks/pieces of evidence). Having the Terrifying Presence Perk will grant a new dialog: "I dug myself out of that grave to plant you in yours, Benny (Attack)".
 * Speak to Yes Man in the suite (13th floor behind the double doors) to find out Benny's plan and the significance of the platinum chip.
 * Once the player has gathered the necessary information, leave the Tops.
 * If you gained any infamy with either the NCR or Caesar's Legion, your reputation will be reset to neutral. Representatives from both factions will approach the player with requests from their respective chiefs to parley.

Detailed Walkthrough
Now that you know Benny is at the Tops casino in New Vegas, it's time to go find him. You can deal with Benny in a few ways:

I. Speak with Swank. There is a series of 3 Speech checks (15, 30, and 45) and there are 3 pieces of evidence (Distinctive cigarette butt, Engraved cigarette lighter, note found in Novac Message: Khan hospitality). With 3 total checks/bits of evidence you can convince him that Benny needs to be taken care of. He'll give you Benny's Suite Key and return all weapons secured when you enter the casino. Find Yes Man in Benny's Suite and return to Swank. If you choose to take Benny out, Swank will send Benny to his room alone, where you can talk with him and also choose to kill him. This won't cause the casino to become hostile to you. There are other dialog options with Swank besides Benny needing to be taken care of, and other options like working with Benny when you talk with him. Killing Benny in his suite, regardless of circumstances will not cause the casino main floor to become hostile to you.

II. If you speak to Benny and choose the peaceful resolution options:
 * He will give you the key to the Tops presidential suite where, upon arrival, Benny will inform you over the intercom next to the elevator that he has no intention of coming up the suite. From here, you may complete a speech check of 35 and another one of 50 to convince Benny you will no longer pursue him or interfere with his plans. Otherwise, Benny will send up his assassins to kill you.
 * If you pass the speech check of 60 to get Benny accompany you up to the Tops presidential suite he will make you an offer. You can accept, kill him, or forgive him and let him escape. No guards will come after Benny's been killed, and the casino will not turn against you. Four guards will come if you forgive him and let him escape.
 * If you choose to forgive Benny in the Presidential Suite, you will receive 1200 XP for the mission. Immediately afterward, you can kill him while he is still in the room and loot his body for the Platinum Chip and Maria. His guards will still attack, even if Benny doesn't make it out of the room, and the casino will not become hostile. This will also exploit a glitch in the script that unlocks the sub-basement elevator (on the 13th floor through Benny's suite), as Benny will begin fleeing towards it but by killing him you will prevent him ever getting there (which would trigger the elevator to be locked again), it's also the only way to access the sub-basement on a console.
 * If you have the Black Widow perk, it is possible to have Benny wait for you at the suite, where you can either kill him then, sleep with him then kill him in his sleep, or sleep with him and then fall asleep. If you sleep with him and fall asleep, he will be gone in the morning and will have left you a note.
 * Benny will then be captured by Caesar's Legion. You will see him at the Fort and Caesar will give you the choice to decide how he dies or you can decide to help him escape. You then have three choices for his death; the first is crucifixion, the second is battle him in the arena in a fair fight, and the third is to kill him on the spot. If you decide to help him escape you will either have to kill all the Legion in the Fort, or give him a stealth boy and a bobby pin to help him escape. You must have a high sneak skill and a stealth boy for yourself or the Legion will become hostile. You can ask him what he will do if you set him free and he tells you that it's your choice; he can either take over the strip at your side or he will walk off into the sunset and never see you again. However it doesn't give you a choice to pick one or the other after that dialog; you can only kill him or set him free. Caesar will also give you the platinum chip and he will ask you to destroy everything Mr. House has made. After that you can leave the Fort but only without the Platinum Chip. Or you could try to steal your weapons back and try to escape somehow.

III. Physically confront Benny on the main floor of the casino. If you talk to Swank beforehand and provide two speech checks/bits of evidence he'll return your weapons and ensure the chairmen stay out of the fight. Without his help the entire casino will turn against you.

Speak to Yes Man/Swank to conclude the quest.

Outcomes:

I. If Benny was killed, Swank becomes the new boss, and the platinum chip is recovered.

II. If Benny escapes with the chip, he will later be caught by the Legion and can be found at The Fort.

You always get the Tops presidential suite key, either during the quest or by finding it on Benny's corpse.

After speaking with Yes Man, you will have another option for New Vegas, opening up the Wild Card series of quests.

If you choose to let Benny live and escape the Tops Casino, but don't wish to help Caesar, you can start the Legion quest so Caesar gives you the chip and kill the guards at the entrance to escape with the chip. This will make you vilified among the Legion.

Behind the scenes
The title of the quest is a reference to Frank Sinatra's 1961 song Ring-a-Ding-Ding.

Bugs

 * If you enter the sub-basement, your companions may not follow you there. When you go back to the hotel, one or more of your companions may not be there. Saving at this point, then reloading the level seems to fix this bug and restore your companions.
 * If you choose to wait for Benny in the presidential suite, nothing may happen after going up to the Presidential Suite. What should happen is a call from Benny at the intercom stating: "Baby, this meet and greet of ours?  Chalk me up for a no show," followed by a short dialog and an ambush by four of the Top's bodyguards. The conversation through the intercom can be initiated by approaching it.
 * The ambush may never happen. Instead, walking towards the elevator triggers a message from Benny: "The cleaners will knock twice. Make sure they're thorough."  This allows further dialogue, but the ambush may never have happened.
 * If you talk to Benny in his room and choose the option "Player says goodbye" he will give you 250 tops chips. This can be repeated as many times as the player wishes.
 * Sometimes, when you tell Benny to leave your suite "You are stinking up my suite" He may stay inside, on the stool, not leaving unless you wait, sleep, or kill him.
 * If you are planning on siding with the NCR, be sure to finish this quest before starting Things That Go Boom. Otherwise, your fame with the NCR will be reset and stuck at Neutral. Same problem may persist with the Legion, though with their quest, Render Unto Caesar.
 * After you sleep with Benny,and choose to sleep,you can get stuck in a endless black screen. (Needs verification for other platforms)
 * Sometimes when you enter the tops you will freeze and nothing will happen (for xbox loading the autosave you get from entering fixes this problem because the greeter must talk to you)
 * If you tell Benny to meet you in the presidental suite,then kill him and take the platinium chip after talking to Swank only a handful of guards become hostile. But if you then go into the presidental suite then Benny will be talking on the intercom and would appear to have fled to The Fort
 * If you decide to kill all the Chairmen in the casino including Benny and Swank, when you try to go up to the Presidental Suite the game will go black forcing you to restart.

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