#1 JBL (2004):

It could come as a shock to everyone that how can a 250+ days WWE Title reign be a transitional one. However, that was true in JBL's case. After Brock Lesnar left WWE in 2004, Chris Benoit was drafted to Raw and Eddie Guerrero wanting out of the main event glory with Kurt Angle suffering from an injury. And, with Triple H not willing to be a part of Smackdown, the Blue Brand was in dire need of a new face.
At that time, the US Champion John Cena was highly over with the WWE Universe. However, he needed some time to be groomed into a main event player, and so did stars like Randy Orton and Batista who would eventually join the Smackdown roster in 2005. This caused WWE to debut the JBL character, a pro-American heel gimmick. The Longhorn Loudmouth won the WWE Championship from Eddie Guerrero at the Great American Bash 2004 in June and proceeded to carry the title until Wrestlemania 21, where he dropped it to John Cena.
Did you know a top WWE Superstar just wrestled outside the company? More details HERE
JBL's title reign lasted 280 days, making him one of the greatest transitional Champions of all time. He also became the longest reigning World Champion exclusive to Smackdown, a record that would be broken 13 years later by AJ Styles.