Death first appeared on June 26th, 1989, arriving at Dilbert's house to kill him. However, he was actually supposed to kill someone named " Gilbert, and was at Dilbert's house by mistake. He decided to wait around until Dilbert died, but Dilbert started to tell a story, and Death fled.
His next appearance was on March 15th, 1990, where he returned to Dilbert's house to collect Dogbert's soul. However, the cunning dog challenged Death to a game, and to humiliate him, Death said the game would be Dogbert catching a Frisbee in his mouth, much to the canine's anger. Dogbert then changed the game to scrabble, and used a rule against limits on the turn's time to outwit Death, saying "See you in August, Bone Boy."
His third appearance was on March 14th, 1995, appearing as a professional auditor working for Dogbert, implying he lost the game, and had to briefly work for the canine. Dogbert was considering buying Path-E-Tech Management, and well aware of the company's history, had Death audit them, saying to the Pointy-Haired Boss, "I use him because he's seen such hideous things that nothing scares him." However, the records did scare Death, and he started screaming. Dogbert casually remarked "That's not the sound you want to hear from your auditor.
Death's next appearance was in two consecutive strips (Thursday, December 19th, 2002, and Friday, December 20th). Dilbert was at a meeting, remarking on how being overworked was killing him, and Death appeared. Dilbert remarked that the Grim Reaper didn't look very grim, to which he replied "Unlike you, I love my job." He then took Dilbert to "Death", a sort of limbo. During the trip, he told Dilbert that he also was happy because he started taking anti-depressants. Dilbert them asked if he was dead, but Death simply replied that he was over his limit for the day, and was only doing "catch and release", then sending the engineer back to the realm of the living.