#4 Matt Hardy
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Along with his brother Jeff, The Hardy Boys defined the Tag Team Division in the Attitude Era. The older Hardy, while not as successful, as his brother, actually found success outside of the WWE in Impact Wrestling. The 45-year-old Matt Hardy proved how creative he was when he created the Broken Universe and was expected to bring that with him when he returned in 2017.
Due to trademark issues, Matt Hardy created Woken Matt Hardy which proved unsuccessful as he was placed in a feud and then aligned himself with Bray Wyatt. Some have pointed to this, as Vince McMahon was unsure of how to book Matt Hardy in the WWE.
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Now, with his contract set to expire in March 2020, there have been rumblings that he could be headed to AEW to lead The Dark Order. Considering the limited schedule that AEW has and the creative freedom he could have in AEW, there is no telling where Hardy will eventually end up.
That being said, it's remarkable that he has still managed to stay relevant, considering that he became a household name back in 1998 and now in 2020, he's still trying new things, much like Chris Jericho.