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Help! Which Halo is best for...

OP PcG4 FithAce 7

Hi. I have a large group of friends who have been bugging me nonstop to host basically another big gamenight. We all play a wide variety of xbox games however Shooters are our forte. We are all quite a bit older than squeaker-age (yet obviously still play xbox nightly so I wont say we are "mature"), yet love to have fun playing & killing each other. We like to do anywhere from knives only (but with a default loadout for everyone), snipers only (with illegal options unavailable & default loadouts available), Dodgeball, Jousting, & other random custom/made-up games (plus your normal mode games too).

Last week we decided to throw together a gamenight, and did it on MW that I hosted for about 7hours. Though at least it had more options to create your own match than alot of other popular recent games, frankly it still sucked. Plus quite a few dont have MW still. So I started looking up ideas for good games that have private multiplayer lobbies with lots of freedom to customize your game rules, loadouts available, etc, and available if you have gamepass.

SOOOOOO Here I am.....

I am sorry to admit I have never actually played Halo except I vaguely remember playing Reach on the 360 for a very short time (less than an hour). I am amazed of how many people say that there is not ANY better game for a gamenight with custom game tweaks/rules than Halo. I know there are quite a few Halos free with gamepass. With the details of what I basically am looking for, of the Halo games w/Gamepass, which Halo would be best???

NOTE: Since I'm not very hands-on familiar with Halos private game customization stuff, I have also tried to look up how to set up a Halo private lobby or how to access all these amazing options I've heard so much about... I think I'm more lost than when I started! lol So if anyone can at least lead me to where I can find instructions to get me started on where to start/go, It would be greatly appreciated.
Thank you for any assistance!
Especially since you don’t have a history with Halo, I would suggest Halo 5. It’s the newest and most polished, and there’s a wide variety of custom games and maps available via the customs and content browser or you can create your own.

Just download the game and start exploring hands on and you’ll get the hang of it pretty quickly.
If you played Call of Duty before, you could have a lot of fun with Halo 4, which is part of Halo: The Master Chief Collection. It has loadouts, perks, and ordnances so it is easy to pick up if you are coming from COD. However, Halo 5 is also fun yet complex because of the variety of custom options and many gamemodes like slayer (which is like team deathmatch), CTF, oddball, strongholds, breakout, extermination, fiesta, and many more. It is easy to pick up but hard to master because of all of the Spartan abilities like sprint, thrusters, smart scope, stabilizer jets, and spartan charge, but it isn't too much of a problem if you and your friends haven't played before.
Also dont forget that mcc has split screen support, halo 5 does not!
I would suggest the Master chief collection.
Split screen, 6 awesome games to play, Firefight, spartan OPS.
And if you like custom games, you are going to LOOOOVE forge!
Halo 5 is pretty polished, but the mcc just has so much!
Play MCC, split-screen, better story etc than Halo 5
mcc, it has like 6 games worth of content in there, the 4 first chief games, reach, a new version of halo 2 along side the old, and the odst campaign all with the same customizable settings they had before, and for some games there are added settings. specifically halo 2 classic which now has skulls in custom game settings, and the anniversary campaigns for the first 2 games but seeing as how you need a game night game you'll probably steer clear of that because those 2 campaigns are 2 player only.
all of the other campaigns only allow 2 per split screen but 4 players can play so if you're using 2 xbox's you and your friends can play the campaign with full access to all the skulls without having to hunt them down like in previous games.
I am sorry to admit I have never actually played Halo except I vaguely remember playing Reach on the 360 for a very short time (less than an hour). I am amazed of how many people say that there is not ANY better game for a gamenight with custom game tweaks/rules than Halo. I know there are quite a few Halos free with gamepass. With the details of what I basically am looking for, of the Halo games w/Gamepass, which Halo would be best???

NOTE: Since I'm not very hands-on familiar with Halos private game customization stuff, I have also tried to look up how to set up a Halo private lobby or how to access all these amazing options I've heard so much about... I think I'm more lost than when I started! lol So if anyone can at least lead me to where I can find instructions to get me started on where to start/go, It would be greatly appreciated.
Thank you for any assistance!
I think your question should be more than "what game", but it should also be "what gametypes". You're going to want 12-16 players for all of these games I have listed below - any less may not work.

The game should definitely be Halo : The Master Chief Collection. With that, you will have almost limitless possibilities of different games and game types to choose from. If you do the right amount of homework, you can set yourself up for a fantastic night of playing with friends. You'll need to know how to change game settings, download custom maps, and gametypes, but as long as you have a problem solving bone in your body and the access to YouTube, you should be okay. You'l notice I don't have anything from Halo: CE or Halo 4 on my list below, mostly because those two games are the most unique, and would be a bit jarring to play at the same time as the others. For CE, the spawns and weapons are a little jacked up as it's an antiquated game, and for Halo 4, the mechanics and loadouts are something that is also unique to Halo and a bit of a hassle to prep beforehand.

Off the top, here are some recommendations. If you have any questions regarding any of them, feel free to DM me and I can try and help you out. I'll list everything in the order as shown below (game, map, gametype, description).

Halo 2 - Terminal - One Bomb Assault - Turn based team objective game type, one team spawns with a bomb and tries to plant it in the enemy base

Halo 2 - Ascension - Tower of Power - 6 v 6 or 8 v 8 game, no radar, no shields, shotguns only. Play to 200 kills, turret on the highest tower. Teams try to fight for control of the tower, using the turret to mow down unshielded opponents

Halo 2 - Lockout - Swords and Shotguns - Team Slayer mode, except only swords and shotguns.

Halo 2 - Midship - FFA Fiesta - Free for all slayer where everyone spawns with random weapons. Truly a chaotic but fun mess.

Halo 2 - One Flag CTF - Zanzibar - Turn based team capture the flag, one team attacks, one defends. Attacking team attempts to pull the flag and take it to the beach where they spawn.

Halo 2 Anniversary - Bloodline - 2 Flag CTF Classic - Classic capture the flag on a fantastic map

Halo 3 - Construct - SWAT - Team Slayer mode, except no shields, and no radar. Battle Rifle and Magnums only. First to 100 kills wins.

Halo 3 - Valhalla - VIP - I like to split this into 4 teams of 4 - on each team there is a member designated as the VIP, usually with an overshield. Only kills of the VIP count as actual kills. VIP switches after the original VIP is killed and respawns. Play to 50 kills.

Halo 3 - Oddball - Guardian - Teams fight for control of "the oddball" (a skull), team that holds the oddball for three minutes total first wins.

Halo 3 - Territories - Sandtrap - Similar to the "domination" gametype in CoD, but turn based, and once a territory is captured, it's captured for good. Teams fight to control or defend the five territories. Team with the most territories captured at the end of the turn base wins.

Halo 3 - Team King of the Hill - Standoff - King of the Hill, first team to control the static hill uncontested for one minute, wins.

Halo Reach - Forged Map (Download) - Grifball- 1 bomb that spawns in the middle assault game type, hammers and swords on an enclosed arena. Bomb carrier has overshield and one-hit melee kill with the bomb. Objective is to plant the bomb in the enemy spawn point, first to 3 or 5 plants wins

Halo Reach - Forged Map (Download) - Fat Kid Zombies - 1 player spawns as the "fat kid" - an intensely overshielded and health amped up player who moves extremely slowly and uses a gravity hammer. All other players form the other team of survivors, attempting to slow the fat kid. When the fat kid kills a survivor, they turn into an extremely fast zombie who has a tiny amount of health and no shields. Play until all survivors have been zombified.

Halo Reach - Spire - Invasion - Like the "Rush" game type in Battlefield, Elites vs Spartans, one team attacks, one defends. As the attacking team completes objectives, they unlock progress in the mission, as well as better weapons and equipment. Each team takes turns taking sides, team that progresses the furthest wins.

Halo Reach - Hemorrhage - Rocket Race - Teams of 3 spawn in rocket warthogs, attempt to knock other teams out of their own warthogs or knock them off course, as they race to complete objective circles placed on the map. First team to complete all objectives wins.

Halo Reach - Slayer - Highlands - 8 v 8 traditional slayer, first team to 100 kills wins. Fantastic map for this game type, with lots of vehicles and power weapons to choose from.