The Ladder Match is one of WWE's oldest and most beloved gimmick matches. There's just something about climbing a ladder and retrieving an object that gets fans going. Maybe it's the brutality of the spectacle or the athleticism showcased during the contest, but the Ladder Match has stood the test of time in WWE.
Countless WWE Hall of Famers have competed in the nearly 100 Ladder Matches in WWE history. Most have been in the prime of their careers when they've taken part in it. However, some participants have taken on the daunting task of competing in a Ladder Match at an advanced age.
10 AJ Styles: 43 Years Old
AJ Styles has aged as phenomenally as any pro wrestler could hope to. It's arguable that even in his 40s, Styles is still as good as he's ever been. That notion was on full display at Clash Of Champions 2020 when "The Phenomenal One" competed in a Triple Threat Ladder Match for the WWE Intercontinental Championship with Jeff Hardy and Sami Zayn.
The match lived up to expectations, as all three men delivered when called upon. Not surprisingly though, Styles shined just a bit brighter than his dancing partners. Styles left the match without the Intercontinental Championship, but he reinforced the fact that he's aging like a fine wine.
9 Rey Mysterio: 45 Years Old
Money In The Bank 2020 was only the 2nd pay-per-view WWE ran after the COVID-19 pandemic hit. With that in mind, the event promised to be unique, to say the least. At age 45, Rey Mysterio was the oldest performer competing for the men's Money In The Bank contract. Despite that fact, Mysterio didn't miss a beat, often outperforming his younger opponents.
The highlight of the match came when King Corbin tossed Mysterio from the roof of Titan Towers onto a secondary roof. The spot would've been impressive for a man half Mysterio's age. When you consider Mysterio's age and all the miles he has on his body, the spot becomes even more impressive. Be it a work or not.
8 Chris Jericho: 45 Years Old
Chris Jericho has proven to be an expert at continuously reinventing himself. That ability has allowed Jericho to remain a main event talent for two decades. As the storyline creator of the Money In The Bank Ladder Match, it only made sense for Jericho to compete for the coveted contract at Money In The Bank 2016, even at age 45.
Obviously, Jericho wasn't a serious threat to win the match. At the time, WWE already had a younger talent earmarked for that spot. Regardless, Jericho's ability to compete in such a high-risk, high-profile match at an advanced age just solidified his status as a legend in the business.
7 Kane: 48 Years Old
At Money In The Bank 2015, Kane entered his final Money In The Bank Ladder Match. Unfortunately, it was as his "Corporate Kane" persona and not the "The Big Red Machine" that had been a fan favorite for years. In hindsight, perhaps "The Devil's Favorite Demon" was way overdue for his final Ladder Match. After all, Kane was almost 50 years old at the time.
Competing in such a high-risk match was unnecessary at that point in Kane's legendary career. The fact that a competitor his size not only regularly competed in but had previously won a Money In The Bank Ladder Match is truly a remarkable accomplishment.
6 Dave Taylor: 49 Years Old
Dave Taylor was a surprising addition to the SmackDown roster in 2006. After originally being brought in as a trainer in WWE's developmental territory, Deep South Wrestling, Taylor proved he still had some gas left in the tank. After successfully teaming with his former WCW tag team partner, William Regal, the pair were granted a WWE Tag Team Championship opportunity.
At Armageddon 2006, Regal and Taylor were supposed to challenge Paul London and Brian Kendrick for the WWE Tag Team Championships. However, that was switched to a Fatal Four-Way Ladder Match. Obviously, Regal and the 49-year-old Taylor were at a disadvantage at that point. Unsurprisingly, they would fail to win the match.
5 Shane McMahon: 49 Years Old
In 2019, Shane McMahon was entrenched in a blood feud with Kevin Owens. After months of back and forth attacks, the two men finally decided to settle the score once and for all. They agreed to compete in a Ladder Match where the loser had to leave WWE.
At 49 years old, Shane McMahon entered one of the most notoriously brutal matches in WWE. It was a hard-hitting affair with both men dishing out and taking their fair share of punishment. In the end, Owens would emerge successfully and send McMahon packing. At least for the time being.
4 Finlay: 51 Years Old
In the mid-90s Finlay was widely regarded as one of the best brawlers in the wrestling business. His smash-mouth hard-hitting style would often leave fans bloodthirsty. By the time Finlay arrived in WWE however, he was well past his prime and had lost a step in the ring, to say the least.
That fact didn't stop WWE from booking the 51-year-old Finlay to compete in his third Money In The Bank Ladder Match at WrestleMania 25. The brawling essence of the match suited Finlay well but he provided very little in the form of ariel prowess.
3 Kevin Nash: 52 Years Old
It was a major shocker to most fans when Kevin Nash made his return at SummerSlam 2011 to attack CM Punk and cost him the WWE Championship. Nash hadn't been seen on WWE programming in nearly eight years and was walking into a completely different landscape than the one he left. After a convoluted feud between Nash and Triple H, the two were booked in a Sledgehammer Ladder Match at TLC 2011.
Unlike a normal ladder match, this didn't end when the sledgehammer was retrieved. Rather, whoever retrieved the sledgehammer was allowed to use it on his opponent. The 52-year-old Nash tried his best, but the match under-delivered. It was an ambitious attempt for a man his age and size.
2 Vince McMahon: 53 Years Old
Vince McMahon is as late a bloomer as you'll ever find in the wrestling business. McMahon didn't start working matches until he was in his early 50s. As the villainous "Mr. McMahon" character, McMahon had to be willing to occasionally mix it up with his top rival, "Stone Cold" Steve Austin. At King Of The Ring 1999, Vince and Shane Mcmahon were pitted against Austin in a Ladder Match for control of WWE.
At the time, the 53-year-old McMahon was by far the oldest Ladder Match competitor ever. McMahon did as well in the match as you'd expect a 53-year-old novice to. Unsurprisingly though, it would be Vince McMahon's one and only Ladder Match.
1 Ric Flair: 57 Years Old
At WrestleMania 22, "Nature Boy" Ric Flair made history by becoming the oldest Ladder Match competitor ever. Flair, along with several others, was vying to become "Mr. Money In The Bank." Shockingly, WrestleMania wouldn't even be Flair's first Ladder Match of 2006. He had completed with then WWE Champion, Edge in a TLC match in January.
Flair left it all in the ring at WrestleMania. The highlight of the night was undoubtedly Matt Hardy suplexing Flair off the top of a ladder. Flair wouldn't win the match, but he'd once again prove why he was "The Man" in the wrestling industry for so many years. A truly impressive feat.