Stickybeard frequently targets the Kids Next Door due to their large stash of candy, and is most closely associated with Numbuh 5, also a lover of candy, who he respects as a rival; he even offered her the position of First Mate and heir aboard his ship in Operation P.I.R.A.T.E., which she turned down. He has aided members of the KND on multiple occasions, including saving them from the great white asparagus monster in Operation A.F.L.O.A.T. and teaming up with Numbuh 5 in Operation L.I.C.O.R.I.C.E. to save Heinrich Von Marzipan from evil pirates made out of licorice, who Stickybeard worked for as a cabin boy on their ship in his youth. He was also on Numbuh 4's bowling team in Operation M.I.S.S.I.O.N.'.. He especially eats candy in a rush, as seen in Operation Q.U.I.E.T..
In Operation V.I.D.E.O.G.A.M.E., Stickybeard is the boss of Operation S.H.I.P.S.H.A.P.E., fought by Numbuh 5. In Operation A.W.A.R.D.S., Stickybeard was nominated for best villain at the Villains' Choice Awards, along with Gramma Stuffum, Mr. Boss, and Father. In Operation G.I.R.L.F.R.I.E.N.D., he tried to steal the Sweater of Sweetness, but was foiled by Numbuh 1. He last appeared in Operation I.N.T.E.R.V.I.E.W.S., where he stole Yipper Card 87 from the Nerd Zombies, which resulted in the Nerd Zombies chasing Stickybeard and his Candy Pirates away.
In real-life, Stickybeard would likely be arrested for breaking and entering, robbery, property destruction, and possibly involuntary manslaughter if anyone was in the houses destroyed by his ship.