Roland becomes a gunslinger at the unheard-of age of 14 after being manipulated into taking the "trial of manhood" by Marten Broadcloak, his father's adviser and an alias of Randall Flagg. Marten has an affair with Roland's mother and makes sure Roland finds out about it, prompting Roland to request his trial in order to gain his guns and exact revenge on Marten. In the trial, Roland must defeat his teacher, Cort, using a weapon of his choosing. He chooses a hawk named David and defeats Cort. Roland sacrifices David to win the fight, setting the tone for Roland's future choices in life. Despite Roland's victory, Cort and Roland's father convince Roland to bide his time before seeking retribution.
Not long after, Roland's father sends him on a mission to the town of Hambry in the Outer Barony of Mejis with his friends Alain Johns and Cuthbert Allgood, who will form the basis of his first ka-tet. While there, he meets
Susan Delgado, whom he falls in love with. He also comes into the possession of a pink crystal ball, one of 13 magical artifacts referred to as "Maerlyn's Rainbow." It was while looking into this artifact that Roland first discovered his destiny to quest for the Dark Tower.
Roland is a 30th-generation descendant of his world's version of King Arthur, referred to in the series as Arthur Eld. In Wizard and Glass, during a flashback to Roland's time in the Barony of Mejis, a letter from his father identifies Steven Deschain as a 29th-generation descendant of Arthur Eld from a side lineage (that is to say, from one of Arthur's many "gillies," or concubines). Even his guns were originally made of the melted-down metal from the legendary Excalibur sword. It is hinted that one must possess this sword, or another sign of the Eld (the line of Arthur Eld) in order to open the door at the foot of the Tower. According to a supplemental prose story by Robin Furth included in The Dark Tower: The Gunslinger Born (issues #7 & #2, respectively), Roland's ancestry traces back to Arthur Eld and Emmanuelle Deschain, the daughter of his seneschal, Kay Deschain, while the Crimson King's ancestry traces back to an affair between Arthur and the Crimson Queen.
Quest for the Dark Tower
Roland is alone at the beginning of the series, following the way of ka, a variant of destiny. The term ka-tet is used for a group of people who are deeply bonded to one another through ka. The eight-book series is about Roland's acquisition of a new ka-tet and the completion of his quest. Roland is the last surviving gunslinger and is possessed (or, as he describes it himself, "addicted") by a quest to reach The Dark Tower, the axis upon which infinite numbers of parallel worlds rotate. (Eddie Dean, an ex-heroin addict and member of Roland's ka-tet, calls Roland a "Tower junkie.") The Dark Tower is under assault by the Crimson King, Lord of Discordia, a Satanic figure bent on destroying the Dark Tower by undermining the "Beams" that support it.
In the first novel, The Dark Tower: The Gunslinger, Roland's original desire is simply to climb to the Dark Tower's top to question whatever god dwells there, but ka has greater plans for him. The ka-tet he acquires during the series bears many resemblances to his childhood ka-tet, who were all killed trying to help Roland on his quest. How he treats his new ka-tet when faced with decisions between their lives and his quest is a key component of the novels. Ultimately, his ka-tet represents a chance for redemption and a means by which he can ultimately change his own ka.
At the end of the seventh novel, it is revealed that he is trapped in a repetitive reincarnation, his "damnation" for his crimes and killings (similar to Stephen King's short story "That Feeling, You Can Only Say What It Is in French", in which he expresses that his idea of hell is repetition.) However, it is also suggested that this eternal repetition is not quite eternal; after his rebirth at the end of the novel, it is revealed that in this particular reiteration of his journey, he possesses the Horn of Eld which in his previous pilgrimages he had lost in the final stand at Jericho Hill, the one major element which was discrepant from his approach to the tower and Childe Roland's approach in Robert Browning's Childe Roland to the Dark Tower Came ("Dauntless the slug-horn to my lips I set...").