No fantasy RPG is complete without the inclusion of various guilds for characters to join and Skyrim is no different, at least in this regard. It's different in plenty of other ways, like how it's so fun despite all the bugs, and how it's been released so many times... but regardless of all that, the guilds are still there providing great quests and entertainment.
The Thieves Guild in particular does an amazing job of taking easily ignored skills like Sneak and Pickpocket and making them into great gameplay. However, the Thieves Guild doesn't just offer more opportunities for fun gameplay, but also a chance for players to get involved in one of the most interesting questlines in the whole game.
10 The Bedlam Job
The Bedlam Job is a radiant quest offered by Delvin Mallory once you have joined the Thieves Guild and can be repeated an infinite number of times, which is great as it's one of the few quests in the game where you actually get to steal more than a couple of items.
The goal is simple: go to the chosen city and steal items worth a total of 500 gold without killing anyone or getting caught. Do the quest enough times and you'll unlock City Influence quests that will open up new fences across Skyrim for you to sell your stolen goods more easily.
9 Imitation Amnesty
After completing some small jobs in Whiterun, Delvin Mallory will ask the player to help him deal with an urgent situation that involves preventing someone from being executed for their crimes. The catch is, you need to steal the Jarl's quarters and forge documents in the steward's quarters to do it.
Thanks to how open Dragonsreach is, there are plenty of ways to approach this quest as there are several routes to each area you need to enter - and if you've played any of the game's main questline, then you can abuse your privileges as Thane of Whiterun to avoid consequences if you slip up.
8 Darkness Returns
In order to complete the Thieves Guild questline, the player is sent to the Twilight Sepulcher to return the Skeleton Key to Nocturnal. This is a pretty big ask as by doing this you are giving up the only unbreakable lockpick in the game. But if you've made it this far, then chances are you're a good enough lockpick not to need it anymore.
The quest also teaches you more about the lore around Nocturnal and the Nightingales of the Thieves Guild, making it one of the more interesting Thieves Guild quests despite it involving little to no sneaking or stealing.
7 Silver Lining
In order to solidify the influence of the Thieves Guild in the city of Markarth, the player is asked to recover a silver mold for Endon, an influential silversmith. On the surface of it, the quest might seem like just another raid on a bandit camp, but when you arrive at Pinewatch you'll soon see why this is a quest for the Thieves Guild.
The entire area is designed to allow players to sneakily navigate through the bandit camp without being seen, presenting you with a myriad of options that range from all-out attack to sneaking by without so much as firing an arrow.
6 Trinity Restored
As the Thieves Guild questline progresses, the player becomes wrapped in a web of intrigue, mystery, and betrayal. Part of this mess involves Karliah, a master thief who invites you to join the order of Nightingales who serve Nocturnal as she attempts to bring a traitor to justice.
Not only is being a Nightingale one of the coolest things you can do as part of the Thieves Guild but this quest also grants you the Nightingale Armor, which is by far one of the best sets of armor in Skyrim, and possibly the very best for a character using a stealth-build.
5 Blindsighted
Blindsighted is the penultimate quest of the Thieves Guild's core storyline and sees the climax of the fight between the Nightingales and their traitor, Mercer Frey. Having tracked the traitor to the Dwemer ruins of Irkngthand, it's up to the player to finish the job.
Survive the traps and enemies of the ruins and you'll face off against Mercer Frey himself in the final boss fight of the Thieves Guild questline. Emerge victorious and you can successfully recover the Skeleton Key he stole from Nocturnal, giving you an unbreakable lockpick to use until you return as part of the final Thieves Guild quest.
4 Loud And Clear
One of the earliest major jobs the player is faced with during their time with the Thieves Guild is Loud and Clear, which involves stealing from a safe on the Goldenglow Estate and burning some of their beehives while you are there.
It's a quest that will truly test your ability to remain undetected as you are forced to destroy the beehives, which risks giving away your position the entire time you are doing it. So maybe pack some invisibility potions or learn a spell or two before taking this job on, particularly if you do it at a low level.
3 Speaking With Silence
Speaking with Silence features one of the most dramatic twists in any Skyrim quest and is unique in how it takes control away from you for a rare, cutscene-like sequence in which you're unable to defend yourself against a betrayal.
After the betrayal leaves you poisoned and unconscious, you are nursed back to health by Karliah, the very person you sought to pursue when the quest started. For such a simple quest, it has a great narrative that gets you invested in the questline and adds weight to the later encounters it involves.
2 The Dainty Sload
After completing five small jobs in Solitude, the player is given an opportunity to expand the influence of the Thieves Guild and unlock a new fence within the city. It's one of the trickiest stealth missions in the whole game if you want to remain undetected as you are trying to sneak around the confined space of a heavily guarded ship.
Successfully navigate around the guards and you'll be able to plant the evidence you stole earlier in the quest. In doing so, you'll frame the captain of the ship for a crime they didn't commit and gain the favor of Erikur who becomes an ally to the Thieves Guild in return.
1 A Chance Arrangement
Often the first quest in a guild's questline is a little dull, acting as an introduction more than a story. However, A Chance Arrangement bucks that trend by immediately throwing the player into a job where they have to use their skills to pull off a robbery in broad daylight.
Brynjolf distracts the crowd while the player breaks into a strongbox before planting the ring they find in the pocket of a nearby member of the crowd. It's an entertaining quest and one that makes use of Skyrim's all too often overlooked Pickpocket skill.