Emotionally, Roland at times appears detached or unsympathetic, often reacting with seeming uncaring or anger at signs of cowardice or self-pity, yet he possess a strong sense of heroism, often attempting to help those in need. He is shown to be mentally 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 greatly lack imagination. He also describes himself as "not very good in thinking around corners", meaning he has a very practical character, never really seeking other meanings or intentions behind what he sees, although he is very perceptive and intelligent. Cuthbert, Roland's best friend in his childhood, once said the gears in Roland's head turn slow, but grind extremely well. Roland is not very patient, especially when he is under stress, and often makes a rotating gesture with his hand, which means 'go on, hurry, move on' in conversations. Similarly, he prefers not to over-plan his actions, trusting greatly in his instinct and skill at improvising according to the situation. He is also shown not to have a great sense of humor: though he knows a lot of riddles he rarely jokes and is visibly irritated at times when Eddie (and in the past, Cuthbert) joke around. Roland is not one for small talk.
In The Waste Lands, Susannah compares Roland first to Marshal Matt Dillon of Gunsmoke, but later comes to believe he is more like John F. Kennedy. While she acknowledges that Roland lacks the president's imagination, both men have similar levels of charisma, cunning, and romance. King often notes Roland's strong sense of romance in his narrations, but describes this aspect of the gunslinger's character as being usually hidden by his more dominant sense of pragmatism.
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 - though when confronted with the choice between saving one of them or getting one step closer to the Tower, he would almost certainly choose the Tower. Roland's silent desperation for the Tower is the driving rhythm of the series; it can be felt most powerfully in "The Gunslinger", wherein Roland's sole desire is the Tower and nothing below it.
Roland's revolvers (sometimes referred to as "the big guns" by other characters) are described as long and heavy, with blued steel (originally from his world's Excalibur) andsandalwood grips. These guns are a major sigil, as they are recognized throughout Mid-World and are used as an identifier of Roland. During the search for more ammunition inNew 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 manufactured ammo. In The GunslingerRoland exhibits a technique for reloading his weapons at blinding speed, though it causes burns to his fingertips when done repeatedly in a short time. He loses this ability at the start of The Drawing of the Three, when the first two fingers of his right hand are bitten off. Even after being crippled, he possesses almost superhuman accuracy and he can draw his guns faster than any other character. Roland is noted as being able to shoot equally well with both hands.
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. Roland can speak five languages, including the High Speech and the Low Speech. He also possess a great deal of knowledge about ka the nature of the world. Roland is also a skilled leader, diplomat, and teacher.
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. Eddie Dean sees Stephen King as a young man and recognizes that he and Roland share many of the same physical features, saying that Roland could be King's father.
Some of his hair is gray or white, but some remains black. His facial features are described as rough (although Susannah once compared them to that of a tired poet; Eddie frequently refers to him as "old long tall and ugly"), and he has light blue eyes, often referred to by characters and Stephen King as "bombardier's eyes." Roland lost his right big toe and his right index and middle fingers, which is problematic as he is right-handed in everything other than shooting. He is a strong and disciplined man, capable of working through injuries and illnesses that would have killed or incapacitated another man. Roland is also unusually tall; at 14, he stood taller than the 16-year-old Susan, and, as an adult, his height exceeds that of his father. In The Dark Tower he is described as having reached an adult height of roughly 6'3".
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 reflection of the experiences of each quest. This is symbolized by his re-acquisition of the Horn of Eld after the version covered in the Dark Tower series, implying that he has learned some of the true values of family and love; he has clearly taken the horn from Cuthbert Allgood's body as he wished rather than leaving it there as he did before.