As for Undertaker, while Mark Henry wasn't a great opponent, this was when they were trying to build Henry into a bit of a "monster." Even though he lost, it still helped him to have faced Undertaker at WrestleMania.
It worked better the way it was.
Yeah? How did it help him? The worst Casket match of all time helped Mark Henry?
U see, if u say Taker vs Kane at WM 14 helped Kane, I'd agree cause it was true. Kane had a main event stay for the rest of Attitude Era facing the likes of Stone Cold, The Rock, Mankind, Big Show, and Triple H in memorable feuds.
If u say Taker vs Orton at WM 21, then I agree cause u just had to take a look at he is now.
What wonder did the match at Wrestlemania 22 do to Mark Henry? Did he win the Royal Rumble? Did he main event Wrestlemania? Did he have memorable feuds with the likes of Triple H, John Cena, Edge, Randy Orton, or Chris Jericho? No, the biggest win of his career lately was against Sheamus on RAW. And that's because he was a jobber.
And I didn't see how defeating Mark Henry serve The Streak any benefit. I'll list the accomplishments of his last 4 WM opponents (cause Henry never accomplished anything and never will). By defeating Batista at Wrestlemania 23, Undertaker defeated someone with:
# Pro Wrestling Illustrated
* PWI Most Improved Wrestler of the Year (2005)
* PWI Wrestler of the Year (2005)
* PWI ranked him #1 of the 500 best singles wrestlers in the PWI 500 in 2005
# World Wrestling Entertainment
* World Heavyweight Championship (4 times)
* World Tag Team Championship (3 times) with Ric Flair (2) and John Cena (1)
* WWE Championship (2 times)
* WWE Tag Team Championship (1 time) with Rey Mysterio
* Royal Rumble (2005)
* Match of The Year 2007 vs. Undertaker at Wrestlemania 23
* Feud of the Year (2007) vs. The Undertaker
# Wrestling Observer Newsletter awards
* Feud of the Year (2005) vs. Triple H
* Feud of the Year (2007) vs. The Undertaker
He also main evented Wrestlemania 21 prior to meeting The Undertaker at Wrestlemania 23. And by defeating him Undertaker have also defeated the entire Evolution members following Triple H at Wrestlemania X-7, Ric Flair at Wrestlemania X-8, and Randy Orton at Wrestlemania 21.
By defeating Edge at Wrestlemania 24, Undertaker defeated someone with:
* World Wrestling Federation / World Wrestling Entertainment
o World Heavyweight Championship (5 times)
o World Tag Team Championship (12 times) with Christian (7), Chris Benoit (2), Hulk Hogan (1), Randy Orton (1) and Chris Jericho (1)
o WWE Championship (4 times)
o WWF/E Intercontinental Championship (5 times)
o WCW United States Championship (1 time)
o WWE Tag Team Championship (2 times) with Rey Mysterio (1) and Chris Jericho (1)
o King of the Ring (2001)
o Mr. Money in the Bank (2005, 2007)
o Slammy Award for Couple of the Year (2008) with Vickie Guerrero
o Fourteenth Triple Crown Champion
o Royal Rumble (2010)
Along the way, The Undertaker also defeated one of the E&C members, both Rated RKO members, and the leader of La Familia.
The last but definitely not the least, by defeating (and retiring) Shawn Michaels at Wrestlemania XXV & XXVI, he defeated someone with:
* Pro Wrestling Illustrated
o PWI Feud of the Year (2008) vs. Chris Jericho
o PWI Match of the Year (1993) vs. Marty Jannetty on Monday Night Raw on May 17
o PWI Match of the Year (1994) vs. Razor Ramon in a Ladder match at WrestleMania X
o PWI Match of the Year (1995) vs. Diesel at WrestleMania XI
o PWI Match of the Year (1996) vs. Bret Hart in an Iron Man match at WrestleMania XII
o PWI Match of the Year (2004) vs. Chris Benoit and Triple H at WrestleMania XX
o PWI Match of the Year (2005) vs. Kurt Angle at WrestleMania 21
o PWI Match of the Year (2006) vs. Vince McMahon in a No Holds Barred match at WrestleMania 22
o PWI Match of the Year (2007) vs. John Cena on Raw on April 23
o PWI Match of the Year (2008)] vs. Ric Flair at WrestleMania XXIV
o PWI Match of the Year (2009) vs. The Undertaker at WrestleMania XXV
o PWI Most Popular Wrestler of the Year (1995, 1996)
o PWI ranked him #1 of the top 500 singles wrestlers of the year in the PWI 500 in 1996
o PWI ranked him #10 of the top 500 singles wrestlers of the "PWI Years" in 2003
o PWI ranked him #33 of the Top 100 Tag Teams of the "PWI Years" with Marty Jannetty in 2003
* World Wrestling Federation / World Wrestling Entertainment
o WWF Championship (3 times)
o WWF European Championship (1 time)
o WWF Intercontinental Championship (3 times)
o WWF/E World Tag Team Championship (5 times) with Diesel (2), Steve Austin (1), John Cena (1), and Triple H (1)
o WWE Tag Team Championship (1 time) with Triple H (1)
o World Heavyweight Championship (1 time)
o Royal Rumble (1995, 1996)
o Fourth Triple Crown Champion
o First Grand Slam Champion
o Slammy Award for Best Slammin' Jammin' Entrance (1996)
o Slammy Award for Best Threads (1996)
o Slammy Award for Squared Circle Shocker (1996) Won for collapsing; Owen Hart accepts the award for making Michaels collapse
o Slammy Award for Master of Mat Mechanics (1996)
o Slammy Award for US West Match of the Year (1996) vs. Razor Ramon in a Ladder match at SummerSlam
o Slammy Award for Leader of the New Generation (1996)
o Slammy Award for Best Finisher (1997)
o Slammy Award for US West Match of the Year (1997) vs. Bret Hart in an Iron Man match at WrestleMania XII
o Slammy Award for Match of the Year (2008) vs. Ric Flair at WrestleMania XXIV
o Slammy Award for Match of the Year (2009) vs. The Undertaker at WrestleMania XXV
I didn't list Michaels Wrestling Observer Newsletter awards cause it's too many to name and the page won't be able to sustain it. By defeating and retiring Shawn Michaels, Undertaker also defeated three Kliq members (including Diesel at WM 12), one of The Rockers, both DX members, and two NWO members.
What did Undertaker gain by defeating Mark Henry again?
Undertaker vs Mark Henry is forever a waste of time and life. It should have been Taker vs Angle and Rey vs Orton.