Diary of a Wimpy Kid Wiki



Diary of a Wimpy Kid Wiki

And even though Roland was a little nervous about monsters and sad about his mom being kidnapped he was also EXCITED because he was about to go on his first ADVENTURE.
Page 11 of Rowley Jefferson's Awesome Friendly Adventure

Roland the Kind is a kid with a pure heart who is an imaginary character created by Rowley Jefferson. He lives in a time when formal education didn't exist. Instead, he educates himself by reading books and practicing the flute. Roland is always shown behaving and having a huge amount of respect to other people, especially towards his parents. He is the only son of his mom and dad and is best friends with Garg the Barbarian, spending a lot of time with him. He is the protagonist in Rowley Jefferson's Awesome Friendly Adventure and strongly resembles Rowley.


Roland was a happy boy that resides in his village being raised under the roof by two loving and caring parents. As a child, he always wanted to go on adventures just like his grandfather once did, but the world outside the village was too dangerous so he spends his time reading books about legendary tales of his grandpa's adventures and spending time practicing the flute despite never complaining about it even if he doesn't enjoy it. He also spends a lot of time hanging out with Garg.


One day, his dad went on a business trip to another village and tells him to look after his mom. Then one morning he notices that it was snowing in the middle of the summer and ran into the kitchen to tell his mom on what he saw but realizes that she was gone. He frantically went outside to ask Mrs. Nettles if she knew what happened to his mother due to her knowing about everyone's business. Mrs. Nettles reveals the White Warlock had kidnapped his mom. This made him worried and disappointed about what his dad was gonna say when he returns from his trip.


Roland putting on his armor.

He decided that he was gonna save his mom, so he went down his basement and put on Bampy's old armor and was ready to go on a adventure.

He gets his best friend, Garg to join him where they cleaned up a village, brought peace to the Tangled Forest between the Pixies and the Trolls and fought Medusa. He meets Sherlock Holmes prior to the fight where he gave background information on Medusa's abilities and why he's here in the first place. After changing Medusa into a different person, she tells Roland to look for the One-Eyed Wizard in order to get his friends back to normal.

Roland meets the One-Eyed Wizard who already knew who he was and the situation that he's currently in. He reveals more details about what the White Warlock was gonna do to Roland's mom mostly wanting to make her his queen. With 10 days left, Roland and the One-Eyed Wizard goes back to Medusa's cave where he deforms his two friends along with all the other victims.

Rowley Jefferson's Awesome Friendly Adventure104- Rowley's Journal location- Razor Range

Roland and his group walking up the hill

Most of them flee out of there however two of the victims decided to stay and help Roland on his expedition.

Roland and his group would get attacked and fight off a variety of Mythology monsters such as Ogres and Dwarves. They discover a castle which Roland and Shae'Vana climbs up and meets Christoph where he joins the group despite Roland's disapproval.

Roland and his group walked for long periods of time. He asks Shae'Vana for the map to see if there's anything they can gather on opening the Ice Fortress. Shae'Vana discovers an elf-like language that shows where the entrance is. Roland was excited to the point where he can't sleep during their final night resting and looked for the map again but discovers that the map was gone. They concluded that Shae'Vanna has stolen the map and the One-Eyed Wizard's eye which causes a fight after the group also discovered that she also stole Roland's bag which was filled with all their supplies. In an attempt to resolve this, Roland created a Suggestion box. Everyone decided just to move forward without a map by following Shae'Vanna's footprints. After escaping a corn maze, they came across a lava river where Lefty would drown while helping everyone cross safely to the other side with Roland looking at Lefty's last moments before he sinks into the lava.

Awesome Friendly Adventure159

Roland telling everyone they need to move forward

Righty was created in place of Lefty where they would walk the remaining nights living off of insects and whatever is available in the desert. Roland was sad when he sat near the riverbank and played a song that summoned the Little Mermaid. He tells her that he misses his mom and everything that happened at this point. The Mermaid pulled out a flute and summons a group of Narwhals which sent them to the Ice Fortress. Roland and the One-Eyed Wizard finds the secret entrance finding the White Warlock but couldn't find his mom however he recognizes that he was Santa Claus. The One-Eyed Wizard tells Roland the whole story where he basically wanted to get revenge on his brother.

Awesome Friendly Adventure206

Roland stabbing the One-Eyed Wizard

This made Roland mad and took a step towards him however was hesitant to make a move. Roland watches a fight go down where he ended up being trapped along his group in Righty's hand. About to run out of oxygen, his mom comes out of nowhere thus releasing them. The One-Eyed Wizard took a step towards her raising his wand however Roland overcomes his hesitation and stabs the Wizard turning him into a good guy.

The battle ends with Santa giving everyone a present and gives Roland the title "Roland the Kind." He says goodbye to his new friends and went back home in Santa's sleigh where he and his family would celebrate Christmas.


When Rowley shows his book to Greg for the first time, one of Greg's criticisms was Roland's hair and him being child-like. Throughout most of the books Greg's criticism are mostly be his child-like personality often shutting down any ideas related to merchandise on Roland that was suggested by Rowley.


Roland exemplifies a kind-hearted nature, evident in his ability to wield Jeremy The Sword and unlock the doors to the Ice Fortress—tasks achievable only through a compassionate spirit. His deep affection for his parents is evident in his readiness to face danger to protect them. Roland's obedience extends beyond his family, as he strives not to disappoint others around him. Greg characterizes him as a "sucker" due to Roland's inclination to prioritize helping and cleaning up a village over his main quest, even when unfamiliar with the area.

Despite his virtues, Roland is not without flaws. He grapples with weaknesses such as being physically frail, sensitive, gentle, and hesitant to engage in combat. These traits, however, become advantageous to the One-Eyed Wizard, who chose Roland for precisely these qualities. Interestingly, Roland demonstrates the capacity to set aside his cautious demeanor and engage in combat when necessary, revealing a dynamic aspect to his character.


Roland is a thin Viking with a helmet with 5 strands of hair coming from his hairline with a mullet haircut. He wears old medieval like clothing resembling a peasant.



His appearance is extremely similar to his counterpart, Rowley Jefferson, being visually skinny and short for someone who looks like a middle school kid.



See Roland/Gallery