10 Most Unsuccessful WWE Tournament Winners

4. Billy Gunn

After years as a tag team specialist, Billy Gunn was ready for a single’s run. Traditionally, the best way to embark on that rise to the top is via the King of the Ring. In 1999, Gunn went through an “injured” Ken Shamrock, a distracted Kane and a legitimately injured X-Pac to ascend the throne. All hail Mr. Ass.

Unfortunately, the single’s run was more of a crawl, as Gunn had lingering D-X issues to deal with before facing The Rock at SummerSlam in a “Kiss My Ass” match. While Vince Russo probably had good intentions by booking Gunn to get a rub from The Great One, it ended up backfiring for the less-charismatic performer as The Rock outshone him in every segment. By September, just three months after winning the crown, Gunn was back to teaming with Road Dogg, his single’s run aborted.