Roland is also very old, and stated to be immortal (he is approximately 336 or 337 years old at the end of his quest).
Roland was born to Steven and Gabrielle Deschain in the land of Gilead. We know his mother used to sing for him the 'Baby-Bunting Rhyme' where he first heard the word 'chassit' at nap times but not at bed, because boys of the gun needed to handle the darkness on their own. We also know about the witnessing the hanging of Hax, a cook who was an ally to Farson and was more than willing to poison the children of Taunton. Roland and his friend, Cuthbert, turned Hax in after accidently over hearing his conversation with a guard. He and his family spent a lot of time on vacation along the shores of Lake Soroni with his pet dog Ringo. When he was a little older he began to follow his father on short trips to Sheriff's Offices in neighbouring cities and once all the way to the Downland Baronies.
Earning of Guns
Marten Broadcloak invited Roland into Gabrielle's bedchamber, displaying for Roland their affair. Furious, Roland challenged his mentor Cort to earn his guns and kill Marten. Cort accepts this challenge, but reminds young Roland that if he fails he will be sent west to the wastelands. (Roland later meets a failed gunslinger, one Eldred Jonas when he travels to Hambry) Roland does not back down from his challenge of Cort. He is allowed one weapon; which he chooses his hawk, David. With this weapon choice Roland triumphs over Cort and earns his guns at the unheard of age of fourteen (Steven earned his at the age of sixteen which made him the youngest at the time). Upon earning his guns, Roland buys a prostitute as a right of manhood. Roland is rudely awakened by his father who tells him that he has forgotten his father's face. Roland replies that he has not and it was with him the entire time during his test against Cort. Steven then tells Roland that Marten is furious for passing this test and plans to kill him (Marten knew Roland would take the test, but did not believe he would be successful).
Love Affair with Susan Delgado
Steven sent Roland (with his ka-tet Cuthbert and Alain) east to the town of Hambry to keep him safe from Marten Broadcloak. In Hambry, Roland met a girl named Susan Delgado along the side of the road. Susan was coming from Rhea of the Cöos' house where she had been checked for her "honesty" (virginity) as well as given a hypnotic suggestion to be triggered by losing her virginity, so that once Mayor Thorin takes her to bed on Reap night, she will cut off all her hair, and be less attractive to Mayor Thorin. Upon meeting Roland (known to her as Will Dearborn) Susan falls in love with him and Roland with her. The love for Susan eventually clouds Roland's reasoning as he knows Susan has been promised to Mayor Thorin. Roland is told by Susan to make love to her which he does. Shortly after making love Susan goes to cut off her hair, but is stopped by Roland - who at first mistook her actions to be an attempt at suicide, and he hurts her wrist taking the sharpened stone away from her, breaking the trance. Eventually, Roland, with Alain's help, hypnotizes Susan to find out why she tried to disfigure herself - under hypnosis she also makes the comment 'it is Pink.' Implying the presence of Maerlyn's Grapefruit - and that it may have uses in addition to the known use of far-seeing and other traditional 'crystal ball' like powers. Roland makes love to Susan many times and eventually impregnates her. Rhea, in the meantime has found out about this thanks to Maerlyn's Grapefruit and is furious. Mayor Thorin is murdered by Roy Depape who leaves Cuthbert's bird skull known as "the lookout" at the scene. Roland and his ka-tet are arrested and taken to jail for killing Mayor Thorin. Roland and his ka-tet manage to escape from jail with the help of Susan. Roland and his ka-tet set out for a battle against The Good Man. Roland tells Susan to hide with Sheemie in a hut in the Bad Grass and wait for his return, if he does not return she is to take his guns to his father and tell him what happened. While waiting for Roland, Susan is discovered by the Big Coffin Hunters and is taken back to town by Clay Reynolds. Susan is held prisoner at Mayor Thorin's house. She is freed by Olive Thorin. Her attempt to escape is proven futile as she is captured once more. She is then taken through town and burned as a Charyou Tree. Her last words were "Roland, I love thee."
Battle with The Good Man
As a boy, Roland and Cuthbert overheard Hax the Cook talking with a soldier about poisoning children in Taunton(a town called Farson in the original draft) for the sake of "The Good Man". Roland and Cuthbert told their fathers thus leading to the hanging of Hax. This is also one of the first times Roland hears about The Good Man. During his visit to Hambry, Roland and his ka-tet discover that Mayor Hart Thorin and the town are allied with The Good Man. Hambry is giving their oil for John Fason's war machines. Whilst in Hambry Roland, Cuthbert, and Alain come across three men working for John Farson "The Good Man". The men are Roy Depape, Clay Reynolds, and Eldred Jonas otherwise known as the Big Coffin Hunters. Roland and his ka-tet defeat the Big Coffin Hunters and also take from them Maerlyn's Grapefruit. Through the Grapefruit, Roland discovered the Tower is certainly a physical reality, not a legend or a concept, and also witnessed Susan's death.
During the return to Gilead Roland's mind become trapped inside the Grapefruit and meets the Crimson King for the first time, from it he learns of their shared ancestry and is eventually saved from it by Sheemie. Roland became obsessed with the sphere in much the same way as Rhea of the Cöos and this obsession made him believe Rhea was after him and due to this he mistakenly kills his mother who tries to steal the sphere from Gilead.
Roland awakens to find his mother dead and is then arrested for her murder. In prison he asks Cuthbert and Alain that if he is to be hanged that they do it and no-one else, later being freed by Aileen Ritter. Upon his release they find Abel Vannay murdered and then his murdered father. Rallying gunslinger apprentices they plan the defense of Gilead. He survives the fall of Gilead and had to flee with the few remaining others. It should be noted that the aforementioned events may be uncanon, as they contradict the events in The Wind Through the Keyhole.
In The Wind Through the Keyhole, after killing his mother, Steven Deschain sends Roland and Jamie DeCurry to Debaria to hunt a skin-man who has been killing the residents. With the help of a young boy named Bill Streeter, the only surviving person of the skin-man's attacks, the duo gets the skin-man. It should be noted that the aforementioned events should be considered canon over the comics.
He decides to venture to the Dark Tower after Sheemie is visited by one of the corporeal manifestations of the Beams. On his way there he, alongside his allies, destroys the Cult of Amoco. He is then betrayed by Randolph and later kills Alain after mistaking him for one of Farson's men.
Afterwards at the Battle of Jericho Hill, all of the gunslingers except Roland and Aileen were killed. Not much is known as to what happened to John Farson after this battle (many suspect that he and Walter Padick are one in the same but this is revealed in The Dark Tower and The Gunslinger Born this is not the case).
Quest for the Tower
Little Sisters of Eluria
After being attacked by the mutants, Roland awakens in a hospital run by vampires. Roland begins to care for one of the vampires, Sister Jenna as she and the others take care of him. Roland also meets a boy named John Norman who tells him the nurses are vampires. Sister Jenna begins to give Roland herbs to help him heal.
Roland discovers the only reason the vampires haven't killed him is because he is wearing a gold necklace with God written on it, something he discovers when John (who is also wearing one) is killed by removing it. Roland and Sister Jenna soon escape but are stopped by Sister Mary the head of the organization. However, Sister Mary is killed by the Jesus Dog, a dog with a cross on it Roland discovered in town. Roland and Jenna go to a cave and sleep.
“The man in black fled across the desert, and the gunslinger followed.” — The first line Stephen King would write in The Gunslinger.
The first actual encounter with Roland Deschain is in the Mohaine Desertas he searches for the Man in Black. As he crosses the desert Roland encounters a hermit by the name of Brown and his bird Zoltan. During his stay with Brown, Roland tells about the town of Tull and his stay there.
Roland had arrived in Tull during his pursuit of the man in black. In Tull, Roland met Nort, a local weed eater who had recently died, and Allie. He takes Allie to bed to discover what happened to the weed eater to which she responds with a story of how Nort died and was brought back to life by the man in black. Roland decides to stay in the town for a bit and meets Sylvia Pittston, the pastor at the local church. She reveals she has been impregnated by the man in black with a child of the Crimson King. Roland uses his gun to rape the unborn child out of Sylvia. An outraged Sylvia turns the entire town against Roland and they begin to attack but the gunslinger uses his guns and kills the entire population of the town of Tull. Roland finishes his story still in the confines of Brown's hut and the next day moves on.
As Roland crosses the desert he comes across a waystation and meets a young boy named Jake. Jake is a boy who seems to be from another world, thus Roland hypnotizes him to reveal where he's from. The boy is actually from New York City and was murdered by a man in black, Roland believes this is the same one he now pursues.
As they prepare to leave, Roland goes down into the cellar for some food. In the cellar a Speaking Demon speaks to Roland, after their palaver Roland reaches into the hole the demon was speaking from and pulls free a jawbone. He and Jake depart from the way starion and begin their trek across the desert. They eventually come to a mountanous range and camp for the night.
Roland awakens to find Jake is missing and goes looking for him. He finds Jake, who is about to be seduced by a succubus. The gunslinger gives the jawbone to Jake and has him go back to camp while Roland seduces the succubus instead. Whilst coupled with the succubus he discovers his fate and the path to the tower. Roland and Jake continue on their venture into the mountains where they come across a gang of Slow Mutants. Roland battles with the mutants and they eventually come upon the exit of the cavern, where the man in black is waiting for them. Jake trips on a bridge leading to the way out and Roland has a choice: to catch the man in black and let Jake die, or save Jake and never catch the man in black. Roland lets Jake fall to his death, forever being haunted by his words "there are other worlds than these." Roland leaves the cavern and finally catches the man in black.
They meet in a golgotha and palaver. The man in black reads Roland's fate from Tarot cards. Roland's fate includes The Sailor, The Prisoner, The Lady of Shadows, death, life (which the man in black burns), and the Tower at the center of everything. The man in black tells Roland he is only a pawn for Roland's true enemy who now controls the Tower itself. The man in black tries to convince Roland to give up on his quest by creating a representation of the universe and showing him how insignificant he is. Roland refuses and is forced into sleep. When he awakens, ten years have passed and there is a skeleton next to him, which he believes to be the man in black.
Roland departs from the golgotha and sits at the edge of the Western Sea contemplating the next step in his quest for the Dark Tower.
The Drawing of the Three
After the encounter with The Man in Black, Roland awakes on the beach tired and disoriented. Here he is attacked by a Lobstrosity, a large lobster like monster. After a fatal encounter where he lost two fingers (on his right hand) a toe and a chunk of flesh the creature is stomped down by the gunslinger. Little did Roland know that he was slowly being poisoned by the creature (which he did suspect) when it slashed at him with its claws and bit at the gunslinger.
The Gunslinger continues walking along the beach knowing that he must "draw the three" as Walter had told him in their Palaver. However the Gunslinger falls very sick from the poison from the Lobstrosity he had encountered. He stumbles about the beach for many days regularly falling and he thinks that he almost meets his end at one time at that cold gray beach. He eventually finds the strength and will to move on as he sees an object in the distance.
Walking for many days he eventually comes to a door standing upon the beach. It looks to lead to nowhere and when seen from the other end it is not visible. Upon opening the door he is thrown into a different world, and the mind of The Prisoner, Eddie Dean, a heroin junky. With Eddie, Roland helps his new acquaintance fight off the gangster Enrico Balazar and his lackeys. It is revealed that Henry Dean was murdered while Eddie ran drugs for Balazar. After the battle with Balazar, Roland beckons Eddie to join him in his quest and a skeptical and untrusting Eddie Dean agrees.
The Waste Lands
“There was a boy... — Roland
Since exiting the door marked "The Pusher" Roland had been having a paradox in his head and living two different timelines. Jack Mort never pushed Jake: so did Jake live or die? Roland's mind is split in two, and both Eddie and Susannah fear Roland is losing mental stability.
While travelling and teaching his new gunslingers, they come upon one of the Old Ones built Beam Guardians: Shardik. The three of them destroy his Thinking Cap, and the Guardian is destroyed. They continue to travel, and the paradox gets more severe, even Jake experiences it in his world.
Later, Roland pulls Jake through The Boy's Doorway, usuing Eddie's Key, and saves Jake from the Dutch Hill Mansion Demon. Roland is glad to have Jake back, and promises never to let him fall again. This is why when the group reaches Lud's bridge and Gasher kidnaps Jake, Roland goes after him as soon as possible.
Roland later finds Jake in Tick-Tock's lair, and kills Gasher. Jake already dealt with Tick-Tock. Jake and Roland then go meet Eddie and Susannah at Blaine's Cradle, and after Susannah solved Blaine the Mono's boarding riddle, board the mono.
Roland then prepares himself for Blaine's live-or-die-contest by preparing some of his best Fair-Day riddles.
Wizard and Glass
In Wizard and Glass, Roland and his ka-tet continue to travel on the suicidal Blaine, as he heads to his "last stop". They attempt to come up with a riddle to appease him, but no riddle stumps Blaine. It is eventually Eddie's nonsense that stops Blaine, as he comes up with jokes and riddles so bizarre, the answer is not evident to Blaine. Blaine short-circuits and the group get off in Topeka, which is now barren, overcome by the super-flu.
The group travels on a broken highway towards an emerald green castle, and on the way Roland tells them about his journey to becoming a gunslinger and the events in the Mejis.
Once the ka-tet reaches the emerald green castle (that looks like the one from the Wizard of Oz), and enter it they find a newly revived Tic-Tock Man. Jake quickly disposes of Tick-Tock and Walter appears. He taunts the ka-tet a bit before leaving, and the group does the same, traveling towards the Callas.
The Wind Through the Keyhole
As the group continues towards Thunderclap, the Callas and The Dark Tower itself, they are faced with a starkblast. The group stays in a building in a town Eddie dubs "Gook Town". Roland then tells his ka-tet of two stories: when he and Jamie DeCurry went to Debaria to dispose of a skin-man that has been killing the residents, and the tale called "The Wind Through the Keyhole".
The tales last overnight, and after the storm has passed, Roland and his ka-tet find themselves closer to the Callas.
Wolves of the Calla
After the events Wizard and Glass and The Wind through the Keyhole Roland's ka-tet travel to the farming village of Calla Bryn Sturgis where they meet the townsfolk, as well as Father Callahan, who was originally introduced in 'Salem's Lot. He and the townsfolk request the ka-tet's assistance in battling against the Wolves of Thunderclap, who come once a generation to take one child from each pair of the town's twins. After a few months of being away, the children are then returned "roont" (ruined) - mentally handicapped and destined to grow to enormous size and die young. The Wolves are due to come in about a month's time. Not only do Roland of Gilead and his ka-tet have to protect the Calla-folken from the Wolves, they must also protect a single red rose that grows in a vacant lot on Second Avenue and Forty-Sixth Street in mid-town Manhattan of 1977. If it is destroyed, then the Tower (which is the rose in another form) will fall.
Song of Susannah
Song of Susannah begins with Roland, Eddie, and Jake wondering how they are going to find Susannah after her escape through Doorway Cave. Fortunately, Roland knows that the Manni know how to use the remnants of magic to re-open the door. The plan is for Henchick and the Manni to open the door twice. Roland and Eddie would go through first to rescue Susannah, while Jake and Father Callahan would go through next to convince Calvin Tower to sell the vacant lot with the rose in it. It does not go according to the plan, though; the groups get sucked through in opposite order. Roland and Eddie are then tasked with buying the lot from Calvin.
Back in 1977, Roland and Eddie are dropped in the middle of an ambush set up by Jack Andolini. They meet John Cullum who helps Roland and Eddie escape the ambush. After they leave store, Cullum takes them back to his house where he tells them of Stephen King, Turtleback Lane, and the "walk-ins". He lends them his old Ford Galaxie truck and is told to head to Vermont.
Roland and Eddie eventually convince Calvin to sell the land. They then search for Stephen King after finding his book Salem's Lot, which told the story of Callahan's life. Once they find King, Roland convinces him to continue writing the Dark Tower Series, as the ka-tet believes that their journey depends on King's writing.
The Dark Tower
The book begins with the ka-tet separated in both time and space. Roland and Eddie are in Massachusetts after convincing Calvin Tower to sell the vacant lot.
Eddie and Roland call John Cullum and convince him to go to New York City and find Moses Carver in order to start the Tet Corporation. They head to Turtleback Lane and travel back to Mid-World through the door behind Cara Laughs, the name of the 19th house on Turtleback Lane which Stephen King lives in.
The tet is reunited in Fedic. They find their way to a door that will take them to Algul Siento with the help of Nigel the robot. Nigel, though, has also been helping Mordred find food and to spy on them.
Roland's ka-tet comes to Algul Siento in order to set the Breakers free and protect the Beams. They are met by a group of Breakers friendly to their cause including Sheemie, Roland's old friend from Mejis. Roland quickly establishes a plan. On the day of the attack, they wreak havoc by lighting several buildings on fire and by approaching the town from different directions in order to create the illusion of many people attacking at once. The battle goes in favor of the tet until the very end, when Pimli Prentiss is able to mortally wound Eddie. Eddie's last words are a warning about a being named Dandelo.
While Susannah stays behind to bury Eddie, Roland and Jake Chambers go back to the Keystone World to save Stephen King's life. The pair recruit the services of Irene Tassenbaum to drive them to the scene of the accident. Jake gives up his life to save King's. Roland buries him along the side of the road and Tassenbaum says that she will return and plant a rose on his grave. Tassenbaum and Roland drive to New York City to see what became of the Tet Corporation. In their absence, the company has flourished. Moses Carver tells his story and returns Aunt Talitha's Cross to Roland. Roland and Oy return to Mid-World through the door in the Dixie Pig.
Roland comes back to Fedic where Susannah is waiting for him. They take a passage under the castle and the mountains, but they are pursued by a todash monster. They manage to fend it off by lighting bones using the Sterno that Susannah had found and that Roland had mocked. When they come out of the tunnel, they find themselves on the Badlands. Their trek becomes very uncomfortable as their clothes are ill-suited to the cold weather.
They come upon Le Casse Roi Russe where they encounter Rando Thoughtful, the King's Minister of State. Thoughtful tells of the Crimson King's last days in his castle. After ordering his servants to commit suicide in front of him and smashing the Wizard's Rainbow, he commits a violent suicide using a spoon and continues towards the Tower as an Undead creature. After leaving the castle, Roland and Susannah hear a scream in the distance. It was the sound of Mordred Deschain eating Thoughtful.
What's left of the tet comes to the White Lands of Empathica. There, they meet an older man in a pleasant dwelling who calls himself Joe Collins. He nearly kills Roland Deschain, Susannah Dean, and Oy while feeding on their laughing response to his comedy stylings. They are saved when Susannah accidentally swats the sore on her mouth and has to go to the bathroom to stop the bleeding. In Collins' medicine cabinet, she finds a note from Stephen King that reveals the fact that Collins is the person that Eddie had warned of, Dandelo. When Susannah comes out of the bathroom, she shoots Dandelo and discovers a secret room where Dandelo had held Patrick Danville captive for many years.
Despite the offer from Stuttering Bill to take them to the Dark Tower on a powered sled, Roland decides to continue on foot. Susannah, who has been haunted by dreams of Eddie and Jake, decides to try and leave Mid-World and find them. She recruits Danville to draw her a door to leave. She shares a tear-soaked goodbye with Roland before going through the door.
Mordred Deschain attacks Roland's camp the last night before Roland would reach the Tower. With the help of Oy, Roland wakes up in time to save himself and kill Mordred. Unfortunately, he was not in time to save Oy's life. Oy's haunting last word is "Olan".
Finally, Roland reaches the field of Can'-Ka No Rey. It is the scene of the final battle between Roland Deschain and the Crimson King. The King is locked outside the tower on a balcony and can only throw sneetches at Roland while waiting for him to be drawn to the Tower. Roland's secret weapon is Patrick Danville, who draws a picture of the King and uses a combination of dye from rose petals and Roland's blood to color the King's eyes. After the picture was complete, Danville is able to erase everything except the eyes, which in turn erases the King's body in real life, and Roland is able to enter the Tower safely.
In the coda, we see Roland climbing the Tower at long last. The rooms in the Tower all depict scenes from Roland's life and each has a distinctive smell. When Roland reaches the top room and looks through the door, he sees the Mohaine Desert, the place where his journey begun in the first book. He is sucked through, his memories fade, and his quest begins anew. This time however, Roland finds himself equipped with the Horn of Eld, the one he had lost before. This appears to be a hint that things may yet change and that Roland may eventually find redemption. The book ends the way The Gunslinger began, with the line, "The man in black fled across the desert and the gunslinger followed."
- The Gunslinger Born
- The Long Road Home
- The Fall of Gilead
- The Battle of Jericho Hill
- "The Little Sisters of Eluria"
- "The Gunslinger"
- "The Way Station"
- "The Oracle and the Mountains"
- "The Slow Mutants"
- "The Gunslinger and the Dark Man"
- The Gunslinger
- The Drawing of the Three
- The Waste Lands
- Insomnia (cameo)
- Wizard and Glass
- The Wind Through the Keyhole
- Wolves of the Calla
- Song of Susannah
- The Dark Tower
- The Dark Tower (film)