Billy Gunn had an underrated career that is still going today in AEW. The best years of Gunn came in WWE during his decade in the top promotion. WWE placed Billy in a few roles of multiple tag teams along with a few singles pushes. There were many ups and downs along the way before his release.

RELATED: Every Version Of Billy Gunn, Ranked Worst To Best

TNA tried to find success with familiar names by adding Gunn to the company under the name of Kip James. The return to WWE led to him having a coaching stint along with a short New Age Outlaws reunion. AEW currently employs Billy as a coach and part-time wrestler teaming with his sons. Any wrestler to stick around that long is bound to have regretful memories. Find out what exactly provided embarrassment for Gunn in wrestling.

10 Rockabilly Gimmick

Billy Gunn and Honky Tonk Man

The first chance at a singles push for Billy Gunn in WWE was a huge flop. Billy and Bart tagged for a few years as the Smoking Gunns until WWE was tempted by the potential of Billy branching out on his own.

RELATED: New Age Outlaws: 5 Best Road Dogg Matches (& 5 Best Billy Gunn Matches)

The Honky Tonk Man started to manage him under the new ridiculous name of Rockabilly. WWE thought the idea looked good on paper to have a legend mentor a young star with a similar gimmick. Fans just looked at Rockabilly as a joke with zero positive momentum coming from it. The pivot to forming the New Age Outlaws with Road Dogg saved Billy’s career.

9 Cute Kip Gimmick

The Beautiful People

TNA tried to find more success with Billy Gunn signing him a few years after his prime. The tag team run reuniting with Road Dogg was hit or miss and ended when Road Dogg left the company. TNA placed Billy into The Beautiful People faction with a new gimmick.

Angelina Love and Velvet Sky played heels obsessed with their looks who bullied other Knockouts. Billy would essentially manage them for matches and do their makeup backstage. The act was entertaining in small doses, but it showed zero value to Gunn’s status as a legend.

8 Disappointing NJPW Match Vs Tanahashi

Hiroshi Tanahashi & Billy Gunn

The later years of Billy Gunn’s career would see him continuing to wrestle on the independent circuit. New Japan surprised many fans by booking him for one of their United States tours hoping to gain interest of the casual fan with an older name.

The spot was huge when Gunn faced off against NJPW icon Hiroshi Tanahashi. Billy was too old to have a compelling match of keeping up with such a performer. The NJPW run of Gunn didn’t go strong enough to continue bringing him back. AEW launching gave Billy a wrestling home when seeking one after WWE.

7 TNA Promos Calling Out Shawn Michaels & Triple H

Voodoo Kin Mafia

TNA convinced Billy Gunn and Road Dogg to target Shawn Michaels and Triple H when WWE reunited D-Generation X in 2006. The legends of Michaels and Triple H brought back DX for an extended period for the first time in five years.

There were already criticisms for TNA paying too much attention to WWE and looking bad for it. The promos from Billy and Road Dogg mocking their former teammates came off as low brow television. Both members of the New Age Outlaws publicly regretted the moment and ended up back in WWE.

6 Getting Kicked Out DX While Injured

D-Generation X

The 2000 run of D-Generation X reunited them to support Triple H’s power as the WWE Champion by helping him retain it. Billy Gunn suffered an injury during this reunion when the group was starting to take form.

WWE wrote him off by having Triple H attack him with the others joining to kick him out. Gunn was removed from television for the rest of the DX heel run. To make it more embarrassing, Road Dogg replaced him with X-Pac to remain in the tag team division.

5 "Publicity Stunt" Wedding With Chuck

Billy & Chuck in WWE

WWE ran into a routine of pushing Billy Gunn in a singles role before sending him back to the tag division with a new partner. The duo of Billy and Chuck Palumbo played a gay couple, playing into stereotypes for heat.

RELATED: Every Version Of Road Dogg, Ranked Worst To Best

Many of these segments wouldn’t work today for obvious reasons, but the wedding was even worse. Billy and Chuck each revealed they were pretending to be gay, and it was all a big publicity stunt for a terrible WWE payoff.

4 Public Firing From WWE Trainer Role For Failing Wellness Test

Billy Gunn

WWE brought Billy Gunn back after the TNA run and years of burying Triple H in shoot interviews. Peace was made with Gunn working closely with Triple H again. The role at the Performance Center saw Billy as one of the first coaches.

All reports indicated Gunn was great in the role with names like Baron Corbin and Tyler Breeze crediting him for helping their careers. Unfortunately, an embarrassing ending would see him failing a drug test due to substances taken for his powerlifting competition on the side. WWE fired Billy and left him without a full-time promotion until AEW hired him for a similar role.

3 Impression Of Devon Dudley In TNA

Billy Gunn as Devon Dudley

TNA tried to recreate the magic of D-Generation X by having the New Age Outlaws try to play the same characters. An outdated act would see them looking terrible for a few segments that crossed the line for the wrong reasons.

Billy Gunn used “blackface” for his impression of Devon Dudley in an uncomfortable impersonation of the Dudley Boyz by the Outlaws. The segment was trashed at the time and is viewed significantly worse all these years later.

2 Losing KMA Match Vs The Rock

The Rock vs Billy Gunn

The biggest push of Billy Gunn’s career came when winning the 1999 King of the Ring tournament. WWE wanted to elevate Gunn into a bigger role after the win. The Rock feuded with Billy as the second biggest program heading into SummerSlam 1999.

WWE added a ridiculous stipulation of the winner having to kiss the loser’s behind afterwards. Rock was obviously winning, but Gunn didn’t even look strong in defeat. The aftermath of having to kiss a large woman’s butt was done to make him look foolish even though he was seeking credibility.

1 The Rock's Promo Calling Him Bart

The Rock promo on Billy Gunn

WWE might have realized Billy Gunn’s main event hopes were already gone when booking the finish of the SummerSlam 1999 match against The Rock. There was a genuine desire to push Billy to the top, but one promo showed the discrepancy in their star power.

Rock cut one of the funniest promos of his career by recreating Billy’s prayers to God ahead of the match. The infamous moment of God referring to Gunn as Bob rather than Billy was hilarious. However, Rock found a new catch phrase when having Billy correct 'God' before dropping the “It doesn’t matter what your name is!” line.

NEXT: New Age Outlaws: 5 Reasons Why Road Dogg Was The Team’s Star (& 5 Why It Was Billy Gunn)