He starts out, in The Colour of Magic, the first book of the series, as a guide for the tourist Twoflower, who hails from the Counterweight Continent, a continent across the disc from the 'hub' continent where Ankh-Morpork is situated. He and Twoflower wander around for quite a while, and get chased by everything from the personification of Death to a Lovecraftian creature named Bel-Shamharoth.

The first book ends with a literal cliff-hanger when he and Twoflower are thrown off the edge of the Discworld by astronomers who want to know the gender of Great A'Tuin, the turtle upon which the disc rides, and have designed a space-ship (bronze and shaped like a fish) to do so.

They both survive, for rather complicated reasons involving the structure of the universe and the necessity of Rincewind's continued existence in order to save the world, and Rincewind becomes a recurring character in the series.

Rincewind is most frequently seen wearing his hat with the word WIZZARD emblazoned across it in sequins (this may be a reference to Roy Wood's rock band Wizzard) and his Luggage, which has hundreds of little legs and follows him everywhere, generally attacking anything it perceives as a threat to Rincewind, or, in fact, anything else it perceives at all.

Rincewind is widely believed by readers to be an elderly man, although the first two books describe him as being young. This is further complicated by cover paintings on some of the books themselves (one showed Twoflower with four biological eyeballs rather than eyeglasses as pointed out in later books) and comments made by Death about Rincewind's life-timer. Every living being on the Disc has an hourglass, usually kept in Death's home, that gradually records his life from birth to death. Rincewind's life-timer is described as resembling something created by a glassblower with the hiccups in a time machine; most likely as a result of his constant mishaps involving magic, the nature of reality, and shiftings into alternate dimensions. This represents something of a curiosity to Death who keeps the hour-glass on his desk. The complicated and sometimes changing nature of the life-timer can not only slow the flow of Rincewind's sand, but also stop and even reverse it. As such, even Death himself is unaware of how old Rincewind is supposed to be or when he will die, likening such an exercise as trying to find the starting point on a roll of really clear sticky tape. However Death does tend to show up when Rincewind is in extreme danger, but this has happened to many Discworld entities who have been heavily involved in magic. Death and wizards have many complicated rules, and Rincewind has at times noticeably been hesitant to divorce himself from being a wizard, albeit a bad one.