* 18 years ago in 1997, the WWF held In Your House: Ground Zero live on pay-per-view from Louisville Gardens in Louisville, Kentucky. This was the beginning of the In Your House shows being three hour long, full price shows, and the change led to a quick turnaround in WWF finances once the pay-per-view buys were accounted for a month or two later. Before, the company was losing so much money that it was the catalyst for Vince McMahon telling Bret hart he had to cut him, defer his money, or renegotiate his contract. After, Vince told Bret he could still afford him, but it was a slew of bad booking ideas that sent Bret packing to WCW at the end of the negotiation window McMahon had allowed.
The main event of the show was the first ever televised singles match between The Undertaker and Shawn Michaels. For all intents and purposes, it was the first match between the two, as the only one before this was a one-off at a house show in Portland Maine on February 26, 1995. This was stemming from Michaels accidentally hitting Undertaker with a chair at SummerSlam, costing him his WWF Championship. Even though Michaels was attacking heel Bret Hart, he turned heel anyway when The Undertaker tried to get revenge.
Anyway, while the match itself is semi-forgotten because the rematch was the debut of Hell in a Cell, it was a great, chaotic brawl. Moments like Shawn Michaels crawling to the "door" for the In Your House set and frantically knocking on it to beg for help would be iconic if the match would be so quickly overshadowed. The match broke down into a no contest thanks to a referee bump and interference from Triple H and Chyna, so it was only natural that the rematch would be in a cage.
* Siz years ago in 2009, Bob Barker guest hosted Monday Night Raw at Allstate Arena in Rosemont, Illinois for a show dubbed "The Price is Raw." While there were some other good ones, like The Muooets, Barker is almost unanimously considered the greatest of all Raw guest hosts/guest stars, and with very good reason.
WWE pulled out all the stops, editing together a great entrance video for Barker and rendering graphics to serve as a facsimile of The Price is Right Set. He got a gigantic standing ovation from the Chicagoland faithful, as this was the rare Raw guest host who the fans actually had reverence for and expected a great show out of. After thanking the fans, he revealed that WWE had built their own version of Contestant's Row by the stage and it was time to play The Price i Raw!
Santino Marella, Jillian Hall, Irwin R. Schyster, and Chris Jericho (with his name tag on his bare chest) all bid on the SmackDown 10th Anniversary DVD set. The first three all very bviously overbid while doing their shtick, while Jericho went off on a soliloquy, and when he said the word "one," Barker accepted his bid as one dollar. If you've ever watched The Price is Right, you can see where this went: Jericho won the DVD! He'd win a trip to Hawaii if he beat MVP next, so obviously, being a heel, he lost.
Later, Kelly Kelly was asking Bob about the charity he established and how proceeds from his book would benefit it when Shawn Michaels and Triple H showed up. Barker wouldn't grant them an early match against Cody Rhodes and Ted DiBiase Jr., but he WOULD let them spin The Big Wheel! No, they didn't build The Big Wheel, they rendered it on a TV monitor. Each spun once among a wheel of Raw talent, determining their opponents for the night: Chris Masters and Randy Orton. The wheel sound effects were dead-on, at least.
A.J. Pierzynski of all people replaced Jericho at Contestants' Row later in the show. Santino won a WrestleMania travel package while answering in the form of a question like he was on Jeopardy. Yes, this actually happened.
Later, Chavo Guerrero complained to Bob about Hornswoggle costing him a match and got karate chopped for his trouble. Yes, this also actually happened. Some of this may sound weird on paper, but it's tremendously entertaining and puts Barker atop the guest host heap.