Hildebrand or Tuppy Glossop, nephew of Sir Roderick in Jeeves and the Yule-Tide Spirit, Jeeves and the Song of Songs, The Ordeal of Young Tuppy, Right Ho, Jeeves, and Much Obliged, Jeeves, a friend of Bertie Wooster's since boyhood who was at Magdalen with him. Frequently mentioned as the fellow Drone who bet Bertie he couldn't swing himself across the swimming pool at the Drones by the rings and looped back the last ring, giving Bertie no option but to drop into the water in faultless evening dress (some time prior to the action of Jeeves and the Yule-Tide Spirit). In Jeeves and the Song of Songs as a result of singing "Sonny Boy" at the Oddfellows' Hall in Bermondsey East he drops his courtship of Cora Bellinger and takes up again with Angela Travers, Aunt Dahlia's daughter. Still betrothed to Angela in The Ordeal of Young Tuppy, Right Ho, Jeeves and Much Obliged, Jeeves. His late father invented a headache cure marketed as Runkle's Magic Midgets, which has earned huge profits for Runkle Enterprises. An Old Austinian who still plays football; light hair, a Cheshire-cat grin, a high, squeaky voice, in build and appearance somewhat resembling a bulldog.

• Jeeves and the Yule-Tide Spirit
• Jeeves and the Song of Songs
• The Ordeal of Young Tuppy
• Right Ho, Jeeves
• Much Obliged, Jeeves