The Wrestlemania brand went to Chicago in 2006 and I was actually there live, but will keep this article of the Wrestlemania Challenge series within the retrospective context as far as re-watching the event because the live view point is another article for another time. This show is generally considered a very good event and it's the last WM that took place with an emphasis on violence before the company started to take a more PG direction. The broadcast kicked off with a tag team title match as Kane and the Big Show defended against the combination of Carlito and Chris Masters. Watching how over Carlito was at this point really shows how much either he under performed or management underused him. There were questions about his work ethic or motivation to get to the next level under the WWE banner, and rumors of a failed drug test led to his release in 2010. Even a decade later, it seems like there was so much more for him to do because he had the charisma, mic skills, and in-ring ability to be a much bigger star. The actual match was fine with some good spots from Kane and the finish saw the champions retain with the choke slam for the pin.
The Money in The Bank match was an entertaining spot fest with a lot of risky bumps. Similar to the previous year, Shelton Benjamin shined again in this environment with an incredible dive to the outside after he ran up the ladder. Plus, the spring board spot onto the ladder was a tremendous display of athleticism. Ric Flair took a huge suplex from the top of the ladder from Matt Hardy, temporarily taking him away from the match before "The Dirtiest Player in The Game" made his way back to ringside. It should be noted that even at an older age, The Nature Boy was one of the most over performers on the show. The finish saw Rob Van Dam, who delivered a splash from the ladder earlier onto Finlay, grab the briefcase for the victory, earning a title shot that he would cash-in a few months later at One Night Stand.
JBL pinned Chris Benoit to win the US title in a decent match, but not anything too spectacular. While JBL is a very entertaining persona, this was a time frame that saw him show some weight gain and he was somewhat clumsy in portions of the contest.
The hardcore match with the benefit of hindsight will probably be remembered as an iconic WM bout. Edge, who was just starting to get a push toward main event status that he would keep for another five years, needed major angles to solidify his position as a legitimate main event talent and this feud was key to that. The Matt Hardy real-life debacle made Edge a hated heel, but this Foley feud made him a star. The barbed wire, the thumbtacks, and obviously the conclusion with the flaming table were insane. The match itself gave Edge a level of credibility because he survived the hardcore "test" of the hardcore legend.
The Boogeyman vs. Booker T was an absolutely nothing match. As great as Booker T is, even he wasn't going to be able to carry Boogeyman to an average match. Granted, any match at this spot on the card wasn't going to be able to follow the hardcore spectacle, but even outside of those circumstances The Boogeyman had nothing to offer besides a shock value gimmick. The Boogeyman won, but this contest is skippable. Thankfully, the card rebounded quickly when Mickie James defeated Trish for the women's championship in a really good match. This was one of the few times up until this point that the women's belt was given time on the show and an angle to build around it. Trish and Mickie are both very talented in the ring, but Mickie's character work in this feud as the stalker fan shouldn't be overlooked either. With that type of gimmick, there's a chance it could be presented as tacky, but Mickie's portrayal made her look like a dangerous heel.
The Undertaker vs. Mark Henry casket match was entertaining, and while it doesn't compare to the WM bouts a few years later that stole the show, it still had its moments. The Undertaker did an incredible drive from the ring over the casket and landed on Mark Henry near the entrance way. The Undertaker won to continue the streak, but at this time frame, the undefeated run wasn't really put in jeopardy yet.
A segment earlier in the show had Vince and the rest of the McMahon family have a hilarious potential conversation with God that saw Vince conclude with a "hallelujah!" Hulk Hogan wasn't on the card, but Vince is still sporting a ridiculous Hogan-level 1998 tan for this contest. Speaking of which, similar to Vince's bout with Hulk at WM 19, his clash with HBK wasn't a technical classic, but it was a memorable sports entertainment match. Obviously, they used a lot of gimmicks to camouflage the fact that Vince isn't Ricky Steamboat in the ring, but Michaels' elbow from the ladder through a table is the type of moment that this match-up was designed to provide the audience. Shawn Michaels got the victory, but the feud continued throughout most of the year.
The World Heavyweight title triple threat match was great and Rey Mysterio's win was one of the most emotional moments in the history of the industry. Don't make any mistake, Rey was over enough to be the champion and unquestionably had the skills to be a world champion so while the angle was booked as a way to honor Eddie Guerrero, Rey's extensive main event accomplishments since that time prove that he is undoubtedly a legend in his own right. As far as the actual match, it had a lot of good action, including the double German suplex that launched Rey across the ring and the eventual pin fall that generated a tremendous reaction from the audience.
Candice Michelle vs. Torrie Wilson in a playboy pillow fight was a segment when we were all winners.
The main event was John Cena defending his championship against Triple H, who had monopolized the WM main event spot for the past several years and would continue to do so in the years that followed. This was an intense contest that used the back and fourth action to build great drama throughout it. The crowd was electric and added a lot to this contest. Finally, Cena retained the belt when Triple H tapped out, but he dropped it a few months later to Rob Van Dam at the One Night Stand pay-per-view.
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