10 Funniest Moments Of The Undertaker's Career, Ranked

The Undertaker is arguably the most iconic character fans have seen in WWE history. They get chills down their spines every time they witness the Deadman make his legendary entrance.

With such a dark character, fans wouldn't have expected any humor to come out of The Undertaker. But the American Badass gimmick enabled him to be himself and adopt the element of humor in his segments and matches.

With that said, let's take a look at ten of the funniest moments in Undertaker's WWE career.

10 There's Something On Your Jacket

The Undertaker was both a rival and ally with Vince McMahon during his time in the biker character. But the boss tried to get the Deadman back out of the six-man WWE Championship Hell in a Cell match at the 2000 Armageddon PPV.

Mick Foley, who was the commissioner, announced Kurt Angle would defend the WWE Championship inside Hell in a Cell against five other superstars. Vince McMahon tried to save Angle by convincing the other contestants to back out.

When he tried his luck with the Undertaker, the Deadman wouldn't buy into the boss's advancements. The Undertaker wanted McMahon to send a message to Foley, and hilariously spat on his suit and walked out, saying there was something on his jacket.

9 It's Good For Your Hair

Current NXT General Manager William Regal is no stranger to on-screen authority roles. He served as the commissioner of the WWE during the Invasion storyline, and he had some hilarious moments with The Undertaker.

During a backstage segment, Regal tried to enforce his authority over The Undertaker and tried to intimidate him. But he should've known that he couldn't do that to the master of intimidation.

The Undertaker did not give in to any of Regal's verbal rant and embarrassed him by pouring tobacco spit on his head, and hilariously told him it was good for his hair.

8 Kurt Angle's Wig

Kurt Angle got his head shaved after losing a hair vs. hair match against Edge at the 2002 Judgement Day PPV. Angle tried to cover up his baldness by wearing a wig and had some funny gear to prevent it from falling off.

The Undertaker walked into Vince McMahon's office on the June 13, 2002, episode of SmackDown while the latter was already having a conversation with Kurt Angle.

Angle and Undertaker were to team up in the main event against Triple H and Hulk Hogan, and Vince McMahon tried to rile them up with a pep talk. However, the Undertaker got distracted at the sight of Kurt Angle's wig and stared at it hysterically before snapping out of his confusion.

7 Royal Rumble Massacre

The Royal Rumble match can be quite unpredictable due to some upset eliminations. The fans witnessed a similar scene at the 2002 Royal Rumble event when the Undertaker got eliminated by a surprising superstar.

The Deadman got into a tussle with the Hardy Boyz and had to take them out. But he took his eyes off of Maven, who was already in the ring and got dropkicked to go over the top rope.

The Undertaker took out his frustrations by attacking Maven throughout the arena and sent him headfirst on to a popcorn machine. The Deadman ate some popcorn and left Maven writhing in pain in the ground.

6 It Turns Me On

While the fans already knew many things about the Undertaker, the Deadman enlightened them on something they never knew about him on the January 29, 2001 episode of Raw.

The Undertaker defeated Haku in a one-on-one match at the event and got attacked by Rikishi afterward. The Samoan duo busted the Undertake open with a steel chair, and it left the Deadman furious backstage.

The Undertaker addressed the beatdown in an interview along with his brother Kane. He said that blood doesn't bother him, and in fact, it turns him on. He also said it turns him on even more to make other people bleed and challenged the Samoan duo to a first blood match on the following episode of SmackDown.

5 Mini Undertaker

The Undertaker entered into a rivalry with John Bradshaw Layfield over the WWE Championship in time for the 2004 SummerSlam event. JBL tried to prove he's a fighting champion and called the Undertaker out on the August 5, 2004, episode of SmackDown.

But he brought out a mini Undertaker to mock the Deadman and tried to tombstone him. The real Undertaker showed up, took out JBL and did his signature pose.

However, the mini Undertaker also tried to do the pose along with the real one. The Undertaker stared down the small imposter and gave him a huge chokeslam to end the segment.

4 You're Mine

New SmackDown General Manager Paul Heyman made Undertaker face both Brock Lesnar and Big Show in a handicap match on the October 23, 2003, episode of SmackDown. The stipulation was that if the Undertaker won the contest, he could challenge any superstar at any event he wants.

Undertaker won but took a post-match beatdown at the hands of his opponents. Vince McMahon came out and tried to mock the Deadman and asked him about his decision.

When the Undertaker said the match would be a Buried Alive match at Survivor Series, McMahon thought Brock Lesnar was going to be the opponent. But the Undertaker chose to face McMahon instead and laughed at his face before hilariously saying, "You're mine," and walking out.

3 Interrupting His Own Funeral

The Undertaker resumed his WrestleMania 21 rivalry with Randy Orton in mid-2005, leading to a match between the two at SummerSlam. Orton emerged victorious in the contest and avenged his loss at WrestleMania.

Orton hosted a funeral for the Undertaker on the September 23. 2005, episode of SmackDown. He and his father Bob Orton brought out a casket with seemingly a lifelike wax mannequin of the Undertaker inside.

However, the fans found out it was the real Undertaker when he opened his eyes while Orton was cutting his promo. It finally dawned on Orton that the mannequin had a striking resemblance to the real Undertaker and took a close look at it.

The Undertaker grabbed Orton by the throat and took him out and let him know that it was not over between them.

2 A Laugh With The Beast

The rivalry between the Undertaker and Brock Lesnar was pretty intense right from the get-go, but they found some time to fool around during their match at the 2015 SummerSlam PPV.

After losing his infamous undefeated streak to Brock Lesnar at WrestleMania XXX, The Undertaker returned to resume his feud with the Beast Incarnate in late 2015. It resulted in a rematch between the two superstars at SummerSlam, and it was a hard-fought contest.

During the match, Brock Lesnar tried to mock the Undertaker and laughed in the Deadman's face. Undertaker went out of the box for a moment and gave a hilarious laugh back at Lesnar before landing a stiff punch to his face.

1 The Takeroonie

Sometimes, the live fans in attendance get to witness some of the greatest moments in WWE history after the show goes off the air. This time they almost saw the Undertaker perform his version of Booker T's Spinaroonie.

After the August 12, 2002, episode of Raw went off the air, several superstars tried to make the Undertaker do the Spinaroonie. The list involved Booker T, Goldust, Triple H, Vince McMahon, and The Rock, and they were hell-bent on making the fans witness the rare sight.

Some of them showed the Undertaker how it's done by doing the Spinaroonie themselves, but the Deadman wasn't going to do it at any cost. He instead sent the crowd home happy after ending the segment by taking out Triple H with the other superstars in the ring.

NEXT: 5 Reasons Why The Undertaker Is The GOAT Of Wrestling (& 5 Reasons Why He Isn't)