When it comes to annual gimmick matches, WWE knows how to put on a show.
The Royal Rumble matches always provide some of the company’s biggest moments, whether it’s a massive return, a surprising debut, or a career-making victory for a superstar on the rise.
The Hell in a Cell match, while it has gotten watered down since being turned into an entire pay-per-view, frequently served as a brutality-filled ending to some of the biggest rivalries in its heyday.
But, there’s a legitimate argument for the Money in the Bank ladder match to be called WWE’s most anticipated of the year.
Between a limited but star-studded field, the creativity that comes from the introduction of ladders, and the overall chaos that ensues the second the bell rings, any Money in the Bank ladder match has been considered a must-watch since the concept’s implementation all the way back in 2005.
Since its creation and heading into the 2021 installment of the Money in the Bank pay-per-view, WWE fans have seen 26 Money in the Bank ladder matches.
Some were spectacular, and some were lackluster. Some were great, and some came up short. But, which should be considered the cream of the crop?
We dove into the archives and picked out the six best Money in the Bank ladder matches in WWE history.
6. Money in the Bank 2014
Arguably the biggest cash-in in Money in the Bank history would not have been possible without this match at Money in the Bank 2014.
Amid his rise from his days in The Shield to his success as a singles star, Seth Rollins entered the Money in the Bank ladder match, vying for a WWE title opportunity against the likes of Dean Ambrose, Dolph Ziggler, Kofi Kingston, Jack Swagger, and Rob Van Dam.
Albeit with some help, Rollins pulled off the first of what would be multiple heists throughout the next year, using Corporate Kane to win the Money in the Bank contract.
It was an action-packed battle that clocks in as one of the longer Money in the Bank ladder matches in the concept’s history, and could be deemed the second-most important Money in the Bank ladder match of all time.
A whopping 273 days later, Rollins would cash in his contract in the midst of WrestleMania 31’s main event, pinning Roman Reigns to win the WWE World Heavyweight Championship for the first time.
5. Money in the Bank 2013
Randy Orton is certainly not the level of wrestler that needs the Money in the Bank ladder match, as it’s generally better suited for mid-card wrestlers in need of a jolt to their careers.
But, Orton winning a WWE Championship opportunity at Money in the Bank 2013 certainly didn’t take away from the quality of the match itself, which also featured Christian, CM Punk, Daniel Bryan, Rob Van Dam, and Sheamus.
In the second-longest Money in the Bank ladder match of all time, Orton delivered a picture-perfect RKO to RVD off the top of a ladder, and took advantage of Paul Heyman betraying Punk to earn Money in the Bank honors for the first time in his career.
The win actually proved to be vital to the rise of Daniel Bryan over the course of the next nine months, so the impact of Orton’s win on the grander scheme of things can’t be overstated.
It was an all-around great match, and is well deserving of a spot in the top five on this list.
4. Money in the Bank 2016
If you were just ranking Money in the Bank matches off the members of the field itself, then Money in the Bank 2016 would probably show up even higher on this list.
How can you go wrong with a match that included Dean Ambrose, Alberto Del Rio, Cesaro, Chris Jericho, Kevin Owens, and Sami Zayn?
The six superstars did a great job of building up the match in the weeks leading up to the event, even participating in a memorable talking segment atop six ladders on Monday Night Raw beforehand, as well.
The talent level was insane, and the match quality itself benefitted as a result. You had the technical ability of guys like Jericho and Owens and the athletic prowess of Cesaro, Del Rio, and Zayn, all combined with the chaotic nature of Ambrose.
It didn’t drag from a time perspective, and everyone had their purpose. It catapulted Ambrose, the match’s winner, to stardom after a mediocre few years, and built towards a monumental WWE World Heavyweight Championship match between all three Shield members that would take place a month later.
If you’re looking for a quality Money in the Bank ladder match with more modern names, this is the pick.
3. WrestleMania 23
This one has a legitimate case for the second spot on this list, which makes sense when factoring in the sheer star power that was packed into this match. Instead, it takes a respectable bronze medal as a third-place finisher.
Anytime you can throw superstars like CM Punk, Edge, Jeff Hardy, and Randy Orton in the same ring, let alone in a ladder match, you’re sure to get some wrestling gold.
Adding in the likes of Finlay, King Booker, Matt Hardy, and Mr. Kennedy is just a cherry on top.
These eight wrestlers gave it their all in this one, putting on a spectacular showcase over the course of 24 minutes at WrestleMania 23.
In one of the most iconic ladder match bumps of all time, Jeff Hardy jumped off the top of a ladder and slammed through Edge, who was laying on a ladder himself, breaking Edge’s ladder in the process.
Orton delivering an RKO off the ladder for the first time in his career was special, and getting the first glimpse of Punk in a match concept that would skyrocket his career in each of the next two years is incredible to think about in hindsight.
Mr. Kennedy winning the match was a great moment, though the payoff (or lack thereof) certainly doesn’t help with fans’ memories of the match.
It’s a solid match in the Money in the Bank concept’s infancy, and really shows just how strong the top two matches on this list truly are.
2. WrestleMania 24
Speaking of Punk’s rise to infamy through the Money in the Bank ladder match, his first win at WrestleMania 24 shows up as the second-place finisher in this all-time countdown.
The field itself wasn’t as legendary as the match’s WrestleMania 23 counterpart. But, it probably had the most perfect roster you could possibly build for a Money in the Bank ladder match.
Packing in some of the most athletic WWE stars of all time, WrestleMania 24 saw Punk, Carlito, John Morrison, and Shelton Benjamin all go to work to highlight their abilities in the best way possible.
On the technical side of things, Chris Jericho added a veteran presence, while Montel Vontavious Porter (MVP) and the reigning Money in the Bank winner Mr. Kennedy joined the fray, as well.
So many impressive moments were packed into a 15-minute match that helped kick off an iconic WrestleMania, between Morrison’s moonsault while holding a ladder and Benjamin’s car crash-esque bump through a ladder late in the match.
Each wrestler got their moment to shine with something memorable, and there wasn’t a single wasted moment throughout the match.
If the timing in which the matches actually occurred was flipped, this would likely take the top pick’s spot as the best Money in the Bank ladder match of all time.
1. WrestleMania 21
How can you compete with the first Money in the Bank ladder match of all time?
In a new concept crafted by Chris Jericho himself, fans at WrestleMania 21 were able to witness the inaugural Money in the Bank ladder match, which had loads of mystery surrounding it at the time.
How would a six-person ladder match play out? What would the fallout be for the person who actually wins the match? How does the concept actually work?
Fans got answers to the latter two questions over the course of the next nine months, but they got an immediate answer to the first one when the match actually took place at the start of the show.
Jericho battled it out with Chris Benoit, Christian, Edge, Kane, and Shelton Benjamin for a shot at whatever world championship Monday Night Raw possessed (the brand had the World Heavyweight Championship at the time, but later received the WWE Championship as a result of John Cena being drafted to Raw in 2005).
The six WWE legends got 15 minutes to kick off a Hollywood edition of WrestleMania, and made the most of the opportunity under the bright lights.
The match had loads of brutality with ladders being used as weapons, and also featured some high-flying action from Benjamin and Benoit, as well.
It got the concept started on the right foot, and set the tone for the rise of Edge as a legitimate, main event-level talent in WWE.
The WrestleMania 21 and WrestleMania 24 ladder matches could easily be considered equals, but nostalgia and history helps propel this one to the title of the best Money in the Bank ladder match of all time.