Although he only appeared in 5 Royal Rumbles, Dean Ambrose was one of the biggest stars in the company for much of the 2010s. He is the only member of The Shield who never won the Rumble. But he's gone on to enjoy a ton of success as Jon Moxley in AEW.
The late great Randy Savage is a WWE Hall of Famer and was one of the biggest stars of the 90s. His contemporaries such as Hulk Hogan, Shawn Michaels, and Ric Flair all have Royal Rumble wins. The Macho Man does not.
WWE literally named a Battle Royal after Andre the Giant, the original big man. The Royal Rumble is built for big men to dominate. Andre only appeared in two Royal Rumbles. He should've been in more and should've won one.
Toward the end of his run in WWE, Big Show had become a throwaway character. However, during his peak, he was one of the best big men of all time. He deserved to win at least once in his 14 appearances.
A true wrestling legend, Mick Foley was a master of character work. He has 9 appearances, including his legendary three in one Rumble, when Cactus Jack, Mankind, and Dude Love all made appearances. During Foley's peak in the Attitude Era, he was unfortunately overshadowed by larger figures. It's understandable why he never won, but he was certainly deserving.
Given all of Kane's Royal Rumble accolades, you figure he would've won one of them. Kane has been in 18 Rumbles and amassed 45 eliminations. He was always billed as a tough out, but could never finish the job.
In WWE's defense, had CM Punk not walked out on the company in 2014, he almost certainly would have won one of these by now. There's a decent chance that in two weeks, he's no longer on this list. Punk was and is one of the top stars in the company.
Few wrestlers are more accomplished than Chris Jericho. He's been in every promotion and won just about every title imaginable. The first ever WWE Undisputed Champion, the one thing Jericho never did was win one of his 11 Royal Rumble appearances.
Kurt Angle has had two Hall of Fame careers -- one in WWE and one in TNA. Despite all his successes, though, he never won the Royal Rumble.
Easily No. 1 on this list, just every about wrestling fan will agree Daniel Bryan should have won a Royal Rumble, specifically in 2014. Bryan did end up getting his Wrestlemania moment in what is still one of, if not the greatest Wrestlemania moment of all time. So he's probably not too upset.
