Ring-a-Ding-Ding!

Ring-a-Ding-Ding! is a main quest in Fallout: New Vegas and an achievement/trophy for all platforms

Synopsis
The Courier has come a long way from that grave in Goodsprings, but their search comes to an end when they confront Benny at The Tops.

Detailed walkthrough
Now that the player character knows Benny is at The Tops casino in New Vegas, it's time to go find him. He can be dealt with in a few ways:


 * 1) Speak with Swank. There is a series of 3 Speech checks (15, 30, and 45) or the option to show any of 3 pieces of physical evidence, a distinctive cigarette butt, an engraved cigarette lighter, and/or a Khan hospitality note (found in Novac) or sharing knowledge of Yes Man.
 * 2) * With a total of 3 checks or bits of evidence, Swank can be convinced that Benny needs to be taken care of. He'll give the Courier Benny's suite key and return all weapons secured when entering the casino. Find Yes Man in Benny's Suite and return to Swank. If the path to take Benny out is chosen, Swank will send Benny to his room alone, where he can be spoken to or killed. This won't cause the casino to become hostile. There are other dialogue options with Swank besides Benny needing to be taken care of, and other options like working with Benny when talking to him. Killing Benny in his suite, regardless of circumstances, will not cause the casino main floor to become hostile.
 * 3) * Swank can be spoken to and convinced that Benny needs to be taken care of, but tell him that the Courier is not yet ready, then talk to Benny directly for those speech options, or kill Benny on the Casino floor, without the whole casino going hostile (the four Chairman bodyguards protecting Benny will go hostile, however, and the player character will not get their weapons back from Swank until they tell him they're ready).
 * 4) * Swank can be asked to send Benny back to his suite, alone. He then returns the Courier's confiscated weapons. This way you can't use some "peaceful options" though (see below).
 * 5) If Benny is spoken to and the peaceful resolution option is chosen:
 * 6) * He will give the key to the Tops presidential suite where, upon arrival, Benny will inform the Courier over the intercom next to the elevator that he has no intention of coming up to the suite. From here, a Speech check of 35 and another one of 50 can be used to convince Benny that the Courier will no longer pursue him or interfere with his plans (this option is only available if you confronted Benny in the Casino, not in his suite). Otherwise, Benny will send up his assassins to kill him/her.
 * 7) * If the Courier passes the Speech check of 60 to get Benny to accompany them up to the Tops presidential suite he will make an offer. The offer can be accepted, he can be killed, or he can be forgiven and allowed to escape. No guards will come after Benny has been killed, and the casino will not turn hostile. Four guards will come if he is forgiven and allowed to escape.
 * 8) ** If the player character chooses to forgive Benny in the presidential suite, 1200 XP will be rewarded for the mission. Immediately afterward, Benny can be killed while he is still in the room, and his body looted 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. Killing him 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.
 * 9) * If the player character has the Black Widow perk, it is possible to have Benny wait for them at the suite, where he can either be killed immediately, slept with then killed in his sleep, or slept with after which the Courier may fall asleep. If the Courier sleeps with him and falls asleep, Benny will be gone in the morning and will have left a note.
 * 10) ** Benny will then be captured by Caesar's Legion. He will be seen at The Fort, and Caesar will give the Courier the choice to decide how he dies, or the Courier can help him escape. There are three choices for his death: the first is crucifixion, the second is a battle in the arena, and the third is to kill him on the spot. If it is decided to help him escape, the Courier 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. The player character must have a high Sneak skill and a Stealth Boy for him/herself, or the Legion will become hostile. He can be asked what he will do if set free, and will tell the Courier that it's their choice; he can either take over the Strip at their side, or he will walk off into the sunset and never be seen again. However, it doesn't give a choice to pick one or the other after that dialogue; i.e. to kill him or set him free. Caesar will also hand over the Platinum Chip, and will tell the Courier to destroy everything Mr. House has made. Afterwards The Fort can be left. Or, you could try to steal your weapons back and try to escape somehow.
 * 11) Physically confront Benny on the main floor of the casino. If Swank is spoken to beforehand, and if provided with two Speech checks/bits of evidence, he'll return all weapons and ensure the Chairmen stay out of the fight. Without his help, the entire casino will turn hostile.
 * 12) If Benny is talked to, and the Courier then leaves the casino without taking any of the other options, Benny will run away and be captured by Caesar's Legion.

Speak to Yes Man/Swank to conclude the quest.

Outcomes:


 * 1) If Benny was killed, Swank becomes the new boss, and the Platinum Chip is recovered.
 * 2) If Benny escapes with the chip, he will later be caught by the Legion, and can be found at the Fort.

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

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

If the player character decided to let Benny live and escape the Tops Casino, but doesn't wish to help Caesar, it is possible to start the Legion quest so Caesar gives the chip and then kill the guards, or to simply fight through both Cottonwood Cove and the Fort in order to retrieve the chip. Both options will make the Courier vilified among the Legion.

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

Bugs

 * If you talk with Swank, then confront Benny, and after lockpicking the presidential suite and knowing about Servibot, you can convince Swank to send Benny to his room. There's a dialogue option with Benny in which he gives you 250 Tops chips. This dialogue can be looped infinitely.
 * If you choose to wait for Benny in the presidential suite, nothing may happen after going up there. 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 dialogue and an ambush by his four 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 not happen.
 * Sometimes, when you tell Benny "You are stinking up my suite", he may stay 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. The same problem may persist with the Legion with their quest, Render Unto Caesar.
 * After you sleep with Benny, and choose to sleep, you can get stuck in an endless black screen. (Needs verification for other platforms).
 * If you decide to kill all the Chairmen in the casino including Benny and Swank, when you try to go up to the Presidential Suite the game will go black forcing you to restart.
 * If you convince Benny to come up to the suite with you he may stand still. The player can then talk to him and perform the same speech challenge granting unlimited XP.
 * It is possible to get into Benny's suite and talk to Yes Man before advancing Ring-A-Ding-Ding to the correct stage, and question him about Benny's plans. Yes Man must be asked "What's Benny planning to do with the Chip?" in order for the objective "Search Benny's suite" to be completed, but if this question is asked before Swank enables this objective, it cannot be asked again and the objective cannot be completed, and Swank's assistance in the rest of the quest cannot be secured. However, the quest can still be completed.