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Jolly was a sworn brother of the Black Company. He was mentioned in the Annals during their employment in the Lady's Empire. Before that, he was with the Company in Beryl, and made the fateful trip across the Sea of Torments aboard Soulcatcher's giant galley, The Dark Wings, to Opal. He was considered by Croaker to be "professionally sarcastic" and "sour".

The Black Company[]

The razed Forsberger village[]

Jolly was first mentioned in the Annals during the Company's early trek through Forsberg province. He, Longhead, and Doughbelly were part of the advance team which first arrived outside a village that had been razed by the Limper's army. Doughbelly rode back to the main force, and notified the Lieutenant that about 25 of the Limper's drunk men were still inside the village. The Lieutenant ordered his sergeant Elmo to investigate; Elmo chose Otto, Silent, Peewee, Whitey, Billygoat, Raven, Croaker, and three others to accompany him. Doughbelly brought the group to Longhead and Jolly, and they entered the village, which was strewn with corpses of all ages. Jolly was present when Raven shot two of the Limper's men who had been raping the Forsberger girl Darling in the presence of her grandfather Flick. The group departed after the Captain de-escalated the confrontation with the Limper's officer Lane.

Bloody turnip patrol in Oar[]

When the Company was stationed at the fortress in Deal, Jolly accompanied Candy, Raven, Doughbelly and some others including the civilian Flick on one of the last weekly "turnip patrols" to the nearby city of Oar to purchase supplies. They all boarded in a stable owned by an old local named Cornie, who sold them out to the Imperial Colonel Zouad. Jolly and the other Company brothers fled the stable after a dozen local thugs hired by Zouad and his captain, Lane, set fire to the structure. Once outside, the attackers made it clear they only wanted Raven. When Flick threw himself in front of Raven to protect him, he was killed and a melee ensued. Raven was severely wounded with almost thirty cuts, but the Company soldiers slew all the local thugs. Doughbelly and Jolly recognized Lane from Flick's razed Forsberger village, and Candy observed Lane's superior (Zouad) hiding in the shadows during the fight. Candy and Doughbelly reported all this to Elmo and Croaker, which precipitated the Company's revenge against Zouad and his commander: the Limper.

Garrison in Lords and subsequent events[]

Jolly and the rest of the Company later entered the city of Lords. There, Croaker mused how a little girl could become such a powerful evil as the Lady, and how a "giggling, inquisitive toddler could have become a Three Fingers, a Jolly, or a Silent".

Jolly was still with the main body of the Company inside Lords when it was besieged by Harden and other members of the Circle of Eighteen. He would have been very close to the thunderous sorcery duel between the Rebel leaders, and Soulcatcher and Nightcrawler. Jolly was with the Company when they all fled Lords and passed through the Windy Country with the help of Stormbringer's weather spells, keeping the Rebel at bay. Croaker was specifically very pleased to see Jolly at the Stair of Tear, as he had feared Jolly died at Lords.

Jolly's fate after these events was not recorded. However, as he was not among the 10 Black Company survivors of the Battle of the Barrowland many years later, he is presumed to be deceased by the end of The White Rose.