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Greatest Royal Rumble moments, No. 3: Undertaker and Shawn Michaels build their masterpiece

In  the lead up to this year's Royal Rumble, we'll be counting down the 20 greatest moments in the history of WWE's most famous match. This list was determined by a panel that included Geno Mrosko, Bill Hanstock and me. We tried to keep it diverse, with a mix of comedy, emotion, story, and wrestling.

Running up that hill

When we think about Shawn Michaels vs. The Undertaker, you naturally think about their WrestleMania clashes. In back-to-back years, the two Texans gave Michaels one of the greatest retirement angles ever, and took the legacy of the Dead Man to another level.

Those thrilling contests at the 25th and 26th editions of the Granddaddy of Them All were built across years. And some of the best chapters in their epic rivalry occurred at WWE's annual January pay-per-view (PPV), the start of each year's road to WrestleMania, Royal Rumble.

While technically not up for consideration in this series, as it happened at the event but not in the titular match, it's worth mentioning their main event at the 1998 edition of the PPV. Michaels retained his WWF championship with the help of Triple H, Chyna, the New Age Outlaws, Los Boricuas, Kane and Paul Bearer (the Attitude Era, everybody!) in a Casket match. That outcome was integral to HBK's claim that Taker had never beaten him one-on-one, a fact featured in their Mania builds.

It was in Shawn's hometown of San Antonio, fighting for a main event slot at WM22, that business picked up. Taker survived a two-on-one attack by Rated RKO only to have Michaels slide back into the ring while they were setting up a Con-chair-to and toss Randy Orton & Edge.

The Phenom and the Heartbreak Kid were the final two.

From that iconic scene, we're treated to what is essentially a 12 minute preview of their Mania clashes. The two legends traded shots and signature moves, survived one another's finishers and tipped their caps respectfully to one another after the Dead Man sidestepped Sweet Chin Music and dumped HBK over the top rope to win his first Rumble.

Whatever passed between them was put on the back burner for a year, until the tale resumed when they were the first two entrants in the 2008 Rumble. Though the wrestling wasn't as intense, Michaels and Taker do get about six minutes to go mano a mano before the fourth entrant, Bob Holly, is able to survive until the buzzer sounds and we get a true multi-man match.

Each man lasts more than 30 minutes, many of which are spent targeting one another, before Shawn gets a measure of revenge from the year before with a Superkick just after Taker eliminated Snitsky. Paying for the second he afforded to staredown his rival, HBK is thrown out right after by the two men's mutual nemesis Mr. Kennedy. Michaels scampers away while the Phenom takes out his frustration at not being able to go back-to-back on Snitsky.

Despite the obvious set-up, WWE continued to play a slow hand with what they knew was a big money feud. In 2009, Royal Rumble took a year off from playing a marquee role in their issues, as HBK's first shot at the WrestleMania undefeated Streak actually arose out of the end of a storyline with JBL. Michaels not only won his way out of indentured servitude to the millionaire by winning a singles match at the inappropriately named No Way Out, but set up a rematch with a Mania shot at Taker on the line. The build to their first classic at XXV was fairly standard face vs. face, mind games stuff.

Everyone's patience paid off in 2010. At the prior year's Slammy Awards, Shawn revealed how much his loss to the Phenom ate at him. Denied a rematch by his rival, he pinned all his hopes on a third Rumble victory as a way to face the then World Heavyweight champ at Mania. Many felt Michael's vow telegraphed the winner of the battle royal, a belief that was strengthened when he kicked his D-X partner Triple H out shortly after entering.

It was all the more shocking then when Batista eliminated him twenty minutes later, which is actually THE moment out of the many discussed here that was singled out as our third Greatest in history. Clubbed from behind, the Heartbreak Kid flails for the top rope, only to grab handfuls of air and fall to the floor, having failed.

The range of emotions that ripped and rolled across Shawn when he realized he'd lost his chance to challenge Undertaker were breathtaking to behold. His immediate meltdown, attacking the officials who tried to keep him from re-entering the match, was only the beginning. Coming up short in Atlanta set him on an increasingly unhinged path, upon which we'd watch him risk everything for one more shot at the Streak.

One of the most crucial beats in Taker and HBK's legendary tale doesn't even include the Dead Man. But it couldn't have happened anywhere but the Royal Rumble.

Find previous greatest Royal Rumble moments here.

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