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 alias of Randall Flagg.

[citation needed] 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.

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.

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.

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...").

Emotionally, Roland at times appears detached or unsympathetic, often reacting with seeming indifference or anger at signs of cowardice or self-pity, yet he possesses a strong sense of heroism, often attempting to help those in need.

He is shown to be emotionally scarred from the deaths of all his friends and family, often thinking about their words and actions, and he is said (on more than one occasion by himself) to lack imagination.

[citation needed] Roland is also shown to care a great deal for his Ka-Tet, or "Companions in fate", and often puts himself at risk to save or assist them.

During the search for more ammunition in New York City in The Drawing of the Three, the guns are revealed to be chambered close enough to .45 or the .45 Long Colt to use commercially available cartridges.

In The Gunslinger Roland exhibits a technique for reloading his weapons at blinding speed, though it causes burns to his fingertips when done repeatedly in a short time.

[citation needed] In addition to being a master gunslinger, Roland is an experienced traveler, able to hunt, make his own clothes from the skins of animals, and navigate via the stars.

[citation needed] There is a point during the second book at which Roland psychically bonds himself with a murderer named Jack Mort; the combination of the two personages is said to resemble the mannerisms of Arnold Schwarzenegger as he appeared in The Terminator.

[citation needed] In the last novel, it is implied that the gunslinger's mostly cold, ruthless nature is alleviated slightly every time he reaches the Dark Tower and begins his journey again—Whilst his memories are erased, his personality changes in the reflection of the experiences of each quest.