10 Wrestlers Who Should Have Retired Sooner

Pro wrestling is a sport that, for whatever reason, has its athletes go on for way too long. There are obviously exemptions to the rule, such as Stone Cold Steve Austin who retired on top after WrestleMania 19 with his health and integrity intact. Sadly for the pro wrestling industry, wrestlers like Austin are in the minority in terms of retirement.

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No, instead, for every Steve Austin, there are a dozen wrestlers that stayed putting on matches years beyond their expiration date. Without further ado, let's take a look at a few of those wrestlers that were over the hill for years and should've retired much sooner or should've stayed retired.

10 Ric Flair

Let's just get this one out of the way. Ric Flair is one of the greatest wrestlers of all time. With a career spanning four decades and having been part of some of the biggest moments in the industry's history, The Nature Boy became an icon that transcended the world of pro wrestling. However, his career-ending was still extremely sad.

Due to Flair's safe style, he was able to keep working into his late 50s. However, it was clear that Flair was slowing down dramatically and likely should've hung it up a few years before he actually did in 2008, notably retiring after losing to Shawn Michaels at WrestleMania 24. Sadly, he came out of retirement in 2010 to wrestle for TNA, mainly due to financial reasons. His last match came in 2011 against one of his biggest rivals in Sting.

Flair continued wrestling until he was 62 years old, and his coming out of retirement is noted by Flair as the biggest regret of his career.

9 Kurt Angle

Kurt Angle, despite all of his medical and drug issues, continued putting on incredible matches all the way up until the mid-2010s. Angle after more than a decade gone from WWE signed with the company in early 2017, and despite being past his prime, Kurt continued to put on fun matches. Angle's handicap match with The Shield at TLC 2017 and his mixed tag with Ronda Rousey at WrestleMania 34 stand out as highlights of his comeback.

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However, Angle began to quickly decline from that point forward. Angle's last year with the company was especially painful. Angle had few highlights and then went on to have possibly the most forgettable retirement match of all time against Baron Corbin at WrestleMania 35.

8 Scott Hall

Scott Hall was one of the premier faces of the WWE and WCW in the 90s. While he put on some classic performances during that stretch, it's best if fans remember only that stretch in the 90s and forget almost anything that happened in the 2000s.

Hall was an active performer all the way until 2010, mostly appearing under the TNA banner. With a clear decline over the decade, Hall's final years were especially sad. He finally retired in June 2010, not due to his own violation, but after being released from TNA due to legal issues.

7 Terry Funk

Terry Funk's retirement from pro wrestling was essentially a running joke for decades. Funk's first retirement match was in 1983, a full 34 years before he would actually retire from wrestling. Over the course of his career, Funk allegedly had seven billed retirement matches, and his last match wasn't even billed as so.

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Funk finally retired from wrestling at the age of 73. Funk had been out of his prime for a solid two decades before he finally called it quits in 2017. While there have been more drastic declines, there are few who competed as long as Funk.

6 Shawn Michaels

He really had it all, the rare perfect retirement. Shawn Michaels had the greatest wrestling retirement of all time and lost it all. Shawn Michaels had the rare dignity of retiring before it was time, while still in his 40s, he was still one of the greatest wrestlers on the planet when he retired following WrestleMania 26.

Instead, Michaels came out of retirement and made it on this list. After eight years retired and at the spry age of 53, Michaels came out of retirement for another feud with the Undertaker. He had one official match, the main event of the 2018 edition of Crown Jewel, tagging with Triple H against the Brothers of Destruction. The match was one of the worst of the year, and Michaels retired for a second time after the match.

5 Mark Henry

Mark Henry is now one of the voices of AEW and was previously a backstage trainer for WWE before departing in 2021. It's a good thing Henry found a way to transition out of wrestling, because it was years late when he finally decided to retire in April 2018.

Henry had been out of his prime for at least three years when he finally hung up the boots. He talked about retirement for years before he actually did it, notably saying he'd likely retire in his home state at WrestleMania 32. Instead, Henry chugged along for a few more years before retiring after the Greatest Royal Rumble in 2018.

4 Sabu

When Sabu announced his retirement in November this year, most fans were shocked to know that Sabu hadn't retired already. Sans a few matches for TNA in 2019, Sabu hadn't done much of consequence over the 2010s outside of appearing on a few GCW shows.

Considering his style, it's a miracle that he didn't retire sooner. In the end, he retired due to injuries relating to his back, and he should've called it quits a lot sooner. Sabu had been out of his prime for well over a decade before he officially retired.

3 Roddy Piper

A little-known fact is that Roddy Piper didn't officially retire until 2011. While there were some highlights in his later years such as his 2008 Royal Rumble appearance and the WrestleMania 25 showdown with Chris Jericho, even those moments were hard to watch.

It was clear that in Piper's final years, he didn't belong in the ring. While one of the greatest entertainers to ever be in the wrestling business, Hot Rod likely shouldn't have been anywhere near the ring for five-plus years before he was done.

2 Jimmy Snuka

A former foe of the aforementioned Roddy Piper, Jimmy Snuka also stayed around much longer than many fans would've guessed. Snuka didn't officially retire until 2015, just a few days short of his 72nd birthday.

Similar to Piper, he had fun moments in the same style of returns. However, Snuka looked even worse than Piper did, regularly looking out of shape and seemingly unable to take bumps due to his age, anything past 2000 is best forgotten for The Superfly.

1 The Undertaker

The Undertaker's hunt for the perfect retirement led the Deadman to stay active for much longer than he needed. Undertaker began noticeably declining after WrestleMania 30 but kept performing for another six years. During those six years, Undertaker put on some of the worst matches of his entire career. Most notably his match against Goldberg at Super Showdown 2019 is arguably the worst match of his run.

Thankfully, the legend last wrestled in April 2020, following his acclaimed match against AJ Styles at WrestleMania 36. Undertaker made his retirement official at the 2020 Survivor Series pay-per-view.