15 Money In The Bank Matches WWE Fans Will Never Forget

Ladder matches have become a staple of professional wrestling, specifically WWE, with numerous of them becoming the stuff of legend over the years. Shawn Michaels vs. Razor Ramon at WrestleMania 10, the Undertaker vs. Jeff Hardy on "Raw," and more have elevated ladder matches to the next level. Although, no discussion of ladder match history is complete without touching on one of the most famous variations on the match type out there: the Money in the Bank ladder match, which has been a widely-adored part of WWE's creative arsenal since 2005.

The rules of the Money in the Bank ladder match are quite simple. All one has to do is scale a ladder and unhook the briefcase hanging above the ring. This earns the winner a world championship match, anytime, anywhere, within the next calendar year. The only dilemma — aside from choosing when to cash-in once one retrieves the briefcase — is overcoming the multiple other competitors involved in the match who are equally determined to take the Money in the Bank contract for themselves. These matches are generally thrilling, shocking, and overall highly entertaining.

Still, just because you toss a bunch of ladders and skilled athletes in the ring with a title shot on the line doesn't guarantee a memorable match. Not all Money in the Bank matches are created equally, with some proving far more noteworthy than the rest. These 15 in particular proved especially unforgettable, and here's why.

Months before Kane would hoist the blue Money in the Bank briefcase high above his head, the final WrestleMania Money in the Bank ladder match took place. WrestleMania XXVI, emanating from Glendale, Arizona's University of Phoenix Stadium, saw Christian, Drew McIntyre, Dolph Ziggler, Evan Bourne, Kofi Kingston, Matt Hardy, Kane, Montel Vontavious Porter — aka MVP — Shelton Benjamin, and Jack Swagger do battle for a WWE or World Heavyweight Championship opportunity. Suffice to say, all of the wrestlers involved went to great lengths to etch their names in the history books.

As far as Money in the Bank ladder matches go, this one was decent at best, though it had its moments. Shelton Benjamin, Matt Hardy, Kofi Kingston, and Evan Bourne in particular did some entertaining things with the stipulation, but it was all in vain. When it was all said and done, "The All-American American" Jack Swagger won Money in the Bank and stood at the top of the ladder, all smiles, with the MITB briefcase in hand. A mere few years into his WWE run, Swagger had torn through the "ECW" roster, winning the ECW Championship once, but did he really have what it took to become WWE or World Heavyweight Champion?

Swagger cashed-in his contract on the following "SmackDown" to become the new World Heavyweight Champion and embark on a rather uneventful reign that lasted 82 days. If nothing else, this Money in the Bank match is unforgettable because of the poor choice of winner and the lackluster title run that his win created.

The 2012 edition of Money in the Bank took place at the US Airways Center in Phoenix, Arizona, bringing with it two exciting namesake ladder matches. The first, contested between Christian, Damien Sandow, Dolph Ziggler, Cody Rhodes, Santino Marella, Tyson Kidd, Sin Cara, and Tensai, saw Ziggler earn a World Heavyweight Championship match opportunity at the time of his choosing. The second featured a far thinner field of competitors: Chris Jericho, John Cena, Big Show, Kane, and The Miz, with a WWE Championship match hanging in the balance.

Miz, Jericho, Big Show, and Kane all came into the match with prior MITB experience, in some cases having won prior matches. On the other hand, John Cena had never taken part in such a match, but given his status as the face of the company, the odds were good that he'd walk away with the red briefcase. Sure enough, he did so, announcing his cash-in a few days later on "Raw" and challenging WWE Champion CM Punk to a match at "Raw 1000." The two put on a good match, only for Big Show to interfere and attack Cena, ending the match in a disqualification and preventing Cena from winning the title.

Even though he's among the biggest names in wrestling, John Cena will go down in history as the first man to fail at cashing-in a Money in the Bank contract. On the bright side, he has a 100% success rate in MITB matches since the 2012 installment is the only one he's competed in, so at least he can hang one of his many colorful hats on that.

On the same evening that Kane stood tall as the winner of the "SmackDown" Money in the Bank ladder match, a handful of members of the "Raw" roster took part in a ladder match of their own. Chris Jericho, the Miz, Ted DiBiase Jr., John Morrison, Mark Henry, Edge, Evan Bourne, and Randy Orton all walked into Money in the Bank 2010 with their eyes on an opportunity at the WWE Championship, but only one of them could take the red briefcase home. The Miz managed to secure the Money in the Bank contract, drastically altering the course of his career from then onward.

The Miz burst onto the WWE scene proper (not counting his time on "Tough Enough") in 2006, and for a few years, he didn't get a lot to do. He notably found success with Morrison as a tag team, but he didn't really prove himself as a solo act until 2009 into 2010. His hard work led him to become Mr. Money in the Bank, and his good fortune only continued from there. In November of 2010, Miz cashed-in his MITB contract to become WWE Champion for the first time, defended the title against John Cena in the main event of WrestleMania XXVII, and has since become an integral part of WWE programming.

The Miz went from a reality TV star to one of the most talked-about names in professional wrestling. He put in solid work beforehand, but the ascent of "The Awesome One" truly began at Money in the Bank 2010.

WrestleMania 23 is remembered for a handful of reasons these days. There's the Battle of the Billionaires between Vince McMahon and Donald Trump, as well as the show-stealing World Heavyweight Championship match between Batista and the Undertaker. Of course, there's also the Money in the Bank ladder match from that year, featuring Jeff Hardy, Edge, CM Punk, Mr. Kennedy, King Booker, Matt Hardy, Finlay, and Randy Orton. The match was fun to watch and included some breathtaking spots — the most iconic from WWE's resident daredevil Jeff Hardy — but the winner is often overlooked by history.

Mr. Kennedy was the one to unhook the Money in the Bank briefcase that year, guaranteeing himself a WWE or World Heavyweight Championship match at a time and place of his choosing. As we now know, though, this impromptu bout and his theoretical title reign never came to pass. On the May 7, 2007 edition of "Raw," an injured Kennedy put his briefcase on the line in a match against Edge, who defeated his loud-mouthed opponent for the MITB contract. "The Rated-R Superstar" later cashed-in the briefcase on the Undertaker to become the new World Heavyweight Champion.

The sky was the limit for Mr. Kennedy in WWE until it wasn't, with the loss of his Money in the Bank briefcase signaling the downward trajectory of his run in the company. At least he'll go down in history as the first person to ever lose their MITB contract before they got the chance to cash-in.

Just as they were in the previous four years, WWE fans were treated to a Money in the Bank ladder match at WrestleMania 25. Under the bright lights of Houston, Texas' Reliant Arena, Kofi Kingston, Shelton Benjamin, CM Punk, Mark Henry, Finlay, Christian, Kane, and MVP competed for a chance at the WWE or World Heavyweight Championship. All eight of them gave the match everything they had, with Benjamin taking a particularly big risk in pursuit of the MITB contract. However, his efforts and those of six other men were all for nothing as CM Punk took home the briefcase that night.

CM Punk's Money in the Bank win at WrestleMania 25 isn't just notable because it's CM Punk, who has a penchant for staying in the headlines. On that night, he became the first person in history to win two MITB ladder matches and do so in back-to-back matches. Much like he did with his WrestleMania XXIV contract, Punk cashed-in his WrestleMania 25 one to become the new World Heavyweight Champion. He won the title at Extreme Rules 2009 by defeating Jeff Hardy, who he'd go on to feud with throughout the year in one of the most well-remembered rivalries of this era.

WrestleMania 25 saw CM Punk make Money in the Bank history, ensuring that particular match took a special place in the history books. Not to mention, the title reign that came after it thrust "The Second City Saint" into the main event spotlight — even if Punk feels his WWE run was an overall waste of time.

At WrestleMania 22 in 2006, the second Money in the Bank ladder match took place with a shot at either the WWE or World Heavyweight Championship on the line. "Nature Boy" Ric Flair, Bobby Lashley, Matt Hardy, Rob Van Dam, Finlay, and Shelton Benjamin all walked into the Allstate Arena with their eyes on the prize, and they were more than willing to risk life and limb to secure the briefcase. After a highly entertaining match, RVD stood tall as the second-ever Mr. Money in the Bank. With that, "The Whole Dam Show" embarked on arguably the best run of his entire WWE career.

As the Money in the Bank contract holder, RVD became the WWE Intercontinental Champion by defeating Benjamin at Backlash 2006. Though he'd lose the title not long after, it didn't much matter, bearing in mind that he still had a guaranteed world title opportunity in his back pocket. He ultimately cashed-in his sweet airbrushed briefcase in advance, challenging WWE Champion John Cena to a title match at ECW One Night Stand 2006. It took no shortage of intestinal fortitude (and Edge's timely interference), but Van Dam went home with the championship that night, and to top it all off, he was then awarded the ECW Championship once the brand rebooted and held the titles simultaneously.

Rob Van Dam's Money in the Bank win skyrocketed him to the top of the WWE mountain, making him the first — and so far only — person to hold the WWE and ECW Championships at the same time. It's just too bad that Van Dam's real-life circumstances led to the premature end of his Cinderella story.

In June 2016, it came time for the seventh-annual Money in the Bank pay-per-view event, and the field for the year's ladder match was quite impressive. Former "NXT" standouts Sami Zayn and Kevin Owens, seasoned veteran Chris Jericho, and rising stars Alberto Del Rio, Dean Ambrose, and Cesaro looked to scale the rungs and secure an opportunity at the WWE World Heavyweight Championship. Ambrose wound up seizing the opportunity, and much like a handful of past MITB winners, he didn't wait too long to cash-in his contract and add more championship gold to his trophy case.

The Money in the Bank 2016 main event saw a returning Seth Rollins challenge WWE World Heavyweight Champion Roman Reigns for the title. The two former Shield teammates threw everything they had at each other, and when the final bell rang, "The Architect" stood triumphant as the new champion. However, he didn't get much of a chance to celebrate before the final third of the defunct Shield, Dean Ambrose, hit the ring with his briefcase in hand, using it to attack Rollins. The referee called for the opening bell, Ambrose scored the pinfall, and he became the new WWE World Heavyweight Champion.

In addition to having one of the shortest turnaround times in Money in the Bank history, Dean Ambrose's contract win also produced another interesting stat: with his victory over Rollins, who defeated Reigns for the WWE World Heavyweight Championship moments earlier, all three former Shield members held the title in one night. Thus, the 2016 MITB ladder match is among the most memorable of the modern era.