The Prisoner's Dilemma
Back in Elder Scrolls III: Morrowind, players began as they step off a ship, having been released from prison and shipped to a colony off the mainland by special order of the emperor. In Elder Scrolls IV: Oblivion, the protagonist begins in a cell in the dungeon under the imperial capital, and is released by the fleeing emperor, who needs to use a secret exit hidden in the cell, and who has seen the prisoner in his dreams. Even the story of the original Elder Scrolls I: Arena begins with the protagonist regaining consciousness in a prison cell. Now in Elder Scrolls V: Skyrim, we begin on a cart with fellow prisoners, being brought to our execution.
Either as a blessing or as a curse, there seem to be no in-world clues. Nobody runs up to you asking how you've been, or how you escaped. No relatives welcome you back home. I once thought that someone was coming up to me, remembering me from before my imprisonment and demanding recompense for my transgression, but that turned out to be something different. Still, it made me think about what it means to play a game where I know my character had previously been arrested, but where the game world is entirely new.
The Elder Scrolls team has made no secret of their love for starting players off as prisoners. Starting the player as a prisoner not only explains starting without any loot, but also sets up the narrative trajectory from pariah to messiah. Sure, we all know that our characters are heroes of prophesy who will rapidly rise from their lowly beginnings to be praised by commoners and lavished with gifts from quest-giving nobles. We will rise from rags to riches, from scavenged daggers to enchanted blades crafted from foreign dimensions and gifted to us by the gods themselves. We will be masters of the realm, shaping the world through our choices. It's that hopeful expectation that hooks us in with the narrative and progression of loot and skills. Or at least, that's the idea.
A fair number of role-playing-oriented players find themselves distracted by the hook, though. How did I find myself here? After all, the various forms of punishment we start under in Elder Scrolls games tend to imply that we are being punished for something. What did we do to deserve banishment, imprisonment, or beheading — or do we deserve this punishment at all?
Not only that, but imprisonment conjures an adversarial relationship. Whatever we did or didn't do, we either actively chose to break the law, or we are being punished for an accident (or for a crime we didn't commit). At some point, we chose to cross the Empire, or the Empire chose to cross us. In the case of Skyrim, the punishment for that crossing is death.
The protagonist in Skyrim does not show marks of their past life, though you can choose to add scars or other distinguishing marks as part of the character-creation process. The player, inasmuch as the player is concerned with role-play, must here decide what the character was doing on the wrong side of the law.
Every role-player in any game needs to develop an understanding of "Who am I?" and "How did I get here?" (The beautiful house comes later, thanks partly to Quintin Stone or any number of other modders in this case.)
Of course plenty of games go the easy route, starting the protagonist with amnesia as an excuse to dictate the character's identity for the player. When a game allows the player to shape the character, to build a personality as well as a set of skills, a fantastic amount of restraint must be employed by the developers.
Choosing appearance and skills in any RPG partly chooses the character's background. How did you get those skills, those scars? Why do you wear that face-paint, and what does it mean? What does it mean that you have lived your life as that species and race, as that gender? In Skyrim, players don't choose a class or skills. Rather, all characters begin from a common baseline. You are unskilled — devoid of previous experience or training. Whatever you had been before your arrest, it didn't amount to any form of skilled labor, or even exerting enough labor to show up in your muscles.
So the roleplayer is tasked with figuring out a story that jives with these facts. You were arrested and sentenced to death. You have no skills. Nobody knows you. Your destiny is pre-ordained (though you may choose to avoid it); you can only choose the direction from which you approach it. The future is known, it's your past that is in question.