Born in 2984 3A, Wilcome called himself "Jolly" since he really endured the name rather than his original. He was six years old when the Ruffians invaded the Shire and was soon imprisoned with the rest of the Hobbit children. A month later, Wilcome and the children were freed and took shelter during the Battle of Bywater. He developed a close friendship with Samwise Gamgee and attended Bilbo's 111th birthday party. When Sam and Frodo left the Shire, Wilcome and his family were very worried.
Sometime during the War of the Ring, Wilcome received word from the Mayor that Sam, Frodo, Merry, and Pippin were in Rivendell and set on a journey to destroy the One Ring. At the age of seventeen, Wilcome joined the Shire Company under the leadership of Will Whitfoot and set south to Gondor. Wilcome took part in the Battle of Pelennor Fields where he slew about fifteen orcs and two warg riders that were retreating from the battlefield. Inside the city of Minas Tirith, he was happy to see Merry and Pippin, but grew worried when Sam and Frodo were already in Mordor. Wilcome later fought in the Battle of Morannon and died valiantly along with those that died to give Frodo a chance to destroy the One Ring and end Sauron's reign.