Cliff is a gentle, but aimless young man who has recently wandered into the village/town. He doesn't talk about his past, but it is clear that he has no home to return to. Ann, being outgoing and friendly, gets Cliff to open up in both games and thus makes him the rival bachelor (or Ann being the rival bachelorette in later games).
- Harvest Moon 64 - Cliff is a gentle, but private vagabond who is also well-adept at nature and survival. His pet hawk, Kane, keeps him company and hunts wild game for food. With no home, he survives in the mountains but visits the village regularly at the bar or more often, at the ranch since he and Ann have an affinity for animals. If the protagonist does not befriend Cliff by the end of the first year, Cliff will leave the village forever. Cliff and Ann will get married and have a baby should the protagonist befriend both of them and not propose to her.
- Harvest Moon: Back to Nature - Cliff is a shy but kind wanderer who has taken a liking to the friendly folk of Mineral Town. His past is mysterious and he only confides in the town priest, Carter, who in turn recruits the outgoing Ann to help him get acclimated. Cliff run out of funds after the first year and leave town if the player does not intervene. Should the protagonist invite him to work part-time harvesting grapes at the Aja Winery in Fall year 1, Manna and Duke will be impressed with Cliff's work ethic and take him under their wing. From then on, he will be employed and stay in Mineral Town for the rest of the game. He will marry Ann if the protagonist does no pursue her.
- Harvest Moon: Friends/More Friends of Mineral Town - Same role as "Back to Nature." He is now a potential romance interest in "More Friends of Mineral Town."
- Story of Seasons: Friends of Mineral Town - Same role as "Friends/More Friends of Mineral Town." In this version, if the protagonist does not invite Cliff to the part-time work at Adge Winery, he will leave in Winter year 1, but return in the Summer because he wants to repay the kindness of the townsfolk. A cutscene will occur where the Duke will pass by lamenting how busy he is at the winery and the protagonist will suggest that Cliff should work there. He will be extremely grateful and promises to work hard. Added to his role is also a potential romance candidate for the male protagonist.