In the Enchanted Forest, the Sheriff of Nottingham is humiliated by the thief Robin Hood, who also steals his maiden, Marian. Reduced to nothing, the Sheriff becomes a regular drunk. Cora Mills eventually convinces the Sheriff to pretend to be Robin Hood to marry Queen Regina Mills, her daughter, but it fails to fool Regina. One day, he meets Rumplestiltskin, who is searching for Robin Hood, in order to hunt and kill him. The Sheriff agrees to help the Dark One, but states that he will only tell him if, in return, the Sheriff is allowed a night with the "wench" Rumplestiltskin is traveling with, Belle. Rumplestiltskin rips out the Sheriff's tongue and proposes another deal - if he returns the Sheriff's tongue, then the Sheriff will tell Rumplestiltskin where the thief is. With his tongue back, the Sheriff tells Rumplestiltskin that Robin Hood was seen in Sherwood Forest.
In Storybrooke, Keith is usually at a pub called The Rabbit Hole, where he attempts to woo "Lacey" (actually Belle with new memories). While Lacey is on a date with Rumplestiltskin, who wants to get Belle to love him again, Lacey says that she needs to use the restroom. After Lacey has been gone for a long time, Rumplestiltskin eventually goes out the back where he finds Lacey and Keith making out. Keith later apologizes, but Rumplestiltskin, who is fed up of trying to be good, rips out Keith's tongue so he cannot scream and proceeds to beat him with his cane. Rumplestiltskin eventually notices that Lacey is watching, but she appears to be attracted to Rumplestiltskin's dark side, and so he continues giving Keith a brutal beating.
As Robin and Regina struggle to cope with Zelena, they recall their previous encounters with the Sheriff.
- None known (family)
- He is based on the Sheriff of Nottingham from the story Robin Hood.
- S2, E19: "Lacey"
- S4, E17: "Heart Of Gold" (flashback)
- S4, E20: "Mother" (flashback)
- S6, E12: "Murder Most Foul"