#2 Ultimate Warrior

Left in 1996; returned in 2014 to be inducted into WWE HOF
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One of the biggest names from the 1980s and 1990s that left and was thought to never come back to the WWF/WWE was Ultimate Warrior. He was arguably becoming a bigger star than Hulk Hogan during his prime but would leave the company. Warrior had a stint in WCW before retiring from the pro wrestling business altogether in 1998.
He would have one of the longest periods between leaving and coming back to the company (almost 20 years). According to this wife, Dana Warrior, it was actually his last opponent in the company, Triple H, who was allegedly instrumental in getting the unique Superstar back into the WWE fold.
While he didn't return to the company in a physical capacity for matches (like Angle or Goldberg), Warrior did come back as a WWE Legend. The bittersweet reunion was short-lived as he passed away three days after his HOF induction.
The return of one of the biggest stars from the late 1980s and early 1990s signified the old 'never say never' adage regarding people coming back to the company. Some people never thought that CM Punk would be back in the wrestling business, but now, he's a contributor on WWE Backstage. He's not technically contracted to the WWE, but he's talking about wrestling. That's enough for me.
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