One of the most successful strange signings on this list, but certainly also one of the weirdest, Dwight Yorke was signed by former teammate Keane for £200,000. Jetting over from Sydney FC, the Trinidadian was bizarrely deployed as a defensive midfielder - yet proved surprisingly effective, helping the club to the Championship title and automatic promotion. He continued to feature as a squad player the following season, making 20 Premier League appearances and even scoring a goal from his new deep-lying position. When the ageing Yorke finally departed in 2009, he had been firmly accepted by the club for providing stability when it was needed the most. He's a rare example of an incredibly strange signing working to perfection.