Despite being an Undead representation of death and darkness, everyone's favorite zombie/part-time biker wrestler can be Actually Pretty Funny. Laugh In Peace.
Both Undertaker and Kane get one for this. (As an explanation: in the weeks prior to No Mercy, Undertaker had been assaulted, been accused of infidelity, and had his hand broken by Brock Lesnar, and Kane had to deal with the Katie Vick situation.)
This moment, where Bikertaker hands Tommy Dreamer a cup of his tobacco spit and dares him to drink it. Taker is not known for showing much emotion, which makes his expression at 8:16 that much funnier.
During his casket match with Shawn Michaels at the 1998 Royal Rumble, Shawn stood over the casket with Undertaker inside just before closing the lid to do a D-X "Suck It" taunt. Cue Undertaker's arm suddenly shooting up from the casket and grabbingShawn's crotch. The suddenness of it coupled with Shawn's facial expression makes it hilarious.
Northeastern folks might be familiar with radio and television personality Uncle Vito aka Ranger Danger and his comedic mishaps. In these sketches, Ranger Danger effectively demonstrates what not to say or do in front of The Undertaker.
During this interview with Regis and Kathie Lee, Taker seems unusually friendly; not only does he actually shake hands with the hosts, he also gives probably one of the most out-of-character responses of his entire career:
Regis: And how are you, Undertaker?
The Undertaker: (little voice) Fine...
In this earlier interview, he does a better job of remaining in character, but that doesn't stop Regis from poking at him.
Regis: (singsong voice) I see you! Come out, come out, wherever you are!
Apparently, back in in 1992, Simon Cowell thought it would be a good idea for Undertaker to sing a song for the latest WrestleMania album. Oh, dear... Before you ask, yes, WrestleMania: The Album, also featuring Bret Hart, Randy Savage and others, has been inducted into WrestleCrap.
During this 1993 match, Johnny Polo keeps referring to The Undertaker as "The Underwear Taker". Pray no one ever tries that as a gimmick...
A fairly epic backhanded compliment and Take That to Shawn Michaels on the off-air portion of "Shawn Michaels Appreciation Night":
If the wrestling industry had a Mount Rushmore, yours would be the biggest head on it. Take that anywayyou like.
At Elimination Chamber 2010, after smashing John Morrison headfirst into a chamber pod that Chris Jericho tried to hide in, Taker took Morrison by the head, looked at Jericho... And knocked on the chamber pod.
On Steve Austin's podcast, Bruce "Brother Love" Prichard told a story from back in 1991 that is definitely this. He and Undertaker leave the arena after a show and Taker still has his dark coat and creepy pale face and eye circles make-up on. They drive to the next town and get lost in a bad neighborhood. Bruce rolls down a window and asks some guy at a gas station for directions, and the guy hassles him. Then the guy freezes midsentence cause Undertaker sits up like he does in the ring, looks right at the guy and scared the hell out of the guy so bad he gave them the right directions. "WHOA MAN! You wanna go two blocks that way, then go through the light! I'm getting the fuck out of here!"
A promo building up to a match with Goldust at an In Your House PPV, Vince McMahon asks Undertaker how he & Paul Bearer are gonna deal with "the single most bizarre individual in the WWF". 'Taker replies with "Bizarre? You're asking us about bizarre?"