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Roland de Chumsfanleigh, pronounced Chuffley, (which, as Pratchett says, it's not his fault) appears in The Free Wee Men as the son of the Baron on The Chalk, near Lancre. In very typically British fashion the name has extra syllables which are not pronounced just like Cholmondeley (Chumley) and Featherstonhaugh (Fanshawe) something Monty Python sends up with the sketch of the man whose name is spelled Throatwarbler Mangrove but which is pronounced Raymond Luxury Yach-t.

Since I Shall Wear Midnight, Roland is the current Baron.

In The Wee Free Men, he was captured by the Queen of the Elves as a thirteen year old while out hunting, much like in the folk lore stories of Tam Lin and others. However, unlike those heroes, he is the antithesis of every heroic male in every ballad and folktale of the genre being. Other heroes successfully rescue the fair maiden from an eternity in fairyland or escape themselves if there is no fair maiden. Roland on the other hand seems content to just go on living in fairyland forever. He is Initially a rather dull-witted feckless individual, and does not contribute much to his rescue, beyond cracking the nut when directed to by Tiffany Aching which releases the Nac Mac Feegles from their dream prison. When nine year-old Tiffany first meets him in the Queen of Elves domain he is riding on a white horse and says, "'This is my forest!, I command you to do what I say!" (the concept of the Laird of the land being instantly obeyed by the "peasants". This scene is a reference to the ballad of 'Tam Lin' in which Fair Janet is told she can recognize Tam when she goes to rescue him, as he is the only rider on a white horse. Tiffany rescues Roland from the Queen of the Elves armed with nothing but a frying pan. Once they escape the Baron assumes that it is Roland who is the rescuer since he is a boy and older and Tiffany is a young girl who can't even use a sword; such an ending being the usual motif in a story of this genre. Perhaps this is Pratchett's way of hinting that those other legends and folk songs may not have occurred the way they were presented either since the winner always writes the history books. Roland personally apologises to Tiffany for this distortion of the facts but Tiffany claims the real story can remain a secret provided that he rules justly when he becomes Baron. Since then their relationship has developed full of blushing moments and awkward silences, but they both grow in stature as the Tiffany series of books progresses.

In the second book, A Hat Full of Sky, Tiffany goes to Lancre to study witchcraft and Roland gives her a silver horse necklace, the spirit of horse, which she loves and uses to draw on the power of her homeland in times of crisis.

In the third book, Wintersmith, the Nac Mac Feegle reluctantly make him a hero, and he enters the Underworld to rescue the Summer Lady, fight off bogles and return to the land of the living to help correct the damage caused when Tiffany dances with the Wintersmith in the Dark Morris.

His private life is not exactly been all roses. Roland's father eventually falls very ill, and his two scheming aunts (Danuta and Araminta) use their new position as his guardians to rob the family blind. Roland fights back as much as he can, in the process learning a great deal about surviving sieges and the art of insurgency.

At the end of the Wintersmith, Roland gives Tiffany a box of watercolors, one of which is turquoise, which is allegedly very expensive on the Discworld. Throughout the series it is hinted that the relationship between Tiffany and Roland is more than just a friendship; given the gifts he gives her, certainly his feelings for her are strong and she if very jealous when he writes to tell her he as shown someone else his watercolours and gone dancing. However the class divide between them is a significant obstacle to their marriage; he is after all a future baron and she, although a witch, is a shepherd. Her career as a witch also takes precedence over everything, as her future relationship with Preston shows. So it is not surprising that by the fourth book, I Shall Wear Midnight, the 20 years old Roland meets Letitia Keepsake, the daughter of a Duchess, and they become engaged to marry. While he is away from the Chalk on a shopping trip, his father dies - Tiffany going to meet him to break the news and inform him that he is the new Baron. The old Baron's funeral is held the day before the wedding ceremony; the official wedding. However, on the night between, Tiffany performs an ancient marriage ritual with Roland and Letitia to help defeat the Cunning Man.

Roland's name suggests the ballad Childe Rowland about a young boy who has to rescue his sister Burd Ellen (and the brothers who had previously failed in their rescue attempts) from the King of Elfland. However, as stated, Pratchett's version of Rowland is initially worse than useless. Pratchett claims to have not had this ballad in mind saying "I chose Roland because it's a) old b) a solid kind of name, suggesting the kind of boy he is and c) probably, because I used to live next door to a Roland when I was a kid. 'Childe Rowland and Burd Ellen doesn't mean anything to me, I'm afraid, but it's eerie, innit? I think I might start pretending I had that in mind all along:-" However, there are to many similarities to believe that he wasn't at least subconsciously thinking of Childe Rowland, after all it is a well know English ballad. One such is that Tiffany cuts Roland's head off to break the spell/dream, whereas in Childe Rowland, Rowland cuts everyone's head off except Ellen's in order to break the spell on her. ​ Roland is also of course the name of a great French hero on Roundworld , told in Les Chansons de Rolande. He has the same body of legend about him that the British do about King Arthur, up to and including the notion that in a cave somewhere (sometimes in the Vosges, sometimes in the Midi, perhaps in the Languedoc) the great hero lies in sleep, his magical sword Durandal close to hand, waiting to serve France in her hour of greatest need. The historical Roland is said to have been a knight in the 700's, who fought to keep the Moslem world on the Spanish side of the Pyrénées and to prevent it from spilling into France. He is said to have died in defeating Islam in the semi-mythical battle of Roncevaux