The Undertaker is one of the most intimidating characters in pro wrestling history, and his iconic Deadman character has sent chills down the spines of everyone watching and gave even the parents some nightmares, not to mention the children.
However, there were certain moments when The Undertaker stepped away from his dark character to produce some hilarious moments. The American Badass gimmick gave him the opportunity to be his real self in his in-ring career, and it resulted in some of the funniest moments of his career. With that said, let's take a look at ten of The Undertaker's moments which were actually pretty hilarious.
10 Tommy Dreamer Drinking Tobacco Spit
Back in 2002, Tommy Dreamer had a brief gimmick where he proclaimed himself as "Just a Regular Guy" and resorted to disgusting antics like brushing his teeth and his dog's teeth with the same brush and eating food from the floor.
It was during that time when Dreamer had a segment with The Undertaker where the latter dared him to drink his tobacco spit. When Dreamer refused at first, The Deadman goaded him to do it and even spat a wad of chewed-up tobacco into the concoction. To The Undertaker's surprise, Tommy Dreamer slurped it down, and the expression on The Deadman's face was downright hilarious as he couldn't believe what he was witnessing.
9 Bike Failure
The most important prop of The Undertaker's time as The American Badass is the bikes he used to make his entrances. It became an iconic factor in that phase of The Deadman's career, but that turned out to be an embarrassment for The Undertaker at the 2003 Vengeance PPV.
The Undertaker was scheduled to face John Cena at the event, and the Deadman made his usual bike entrance from the stage. However, the bike would malfunction at the wrong time and fail to start, leaving the Undertaker no choice but to leave the bike and start walking to the ring. The Undertaker looked legitimately unhappy about the botch and the live fans and those who were watching at home had a good laugh at the expense of the Deadman.
8 It Turns Me On!
When the Brothers of Destruction entered into a heated rivalry against Haku and Rikishi in 2001, the latter team would get on the Deadman's nerves on the January 29, 2001, episode of Raw. The Undertaker had defeated Haku in a singles match on the show and endured an attack at the hands of Rikishi. The Samoan team would bust The Deadman open with a steel chair and leave him bleeding in the ring.
However, The Undertaker was unfazed after the ambush and addressed the Samoan duo in a backstage interview. He addressed the beatdown he endured at the hands of Haku and Rikishi and hilariously went on to say that blood doesn't bother him, and in fact, it turns him on. He then added that it turns him on, even more, when he makes other people bleed and proceeded to challenge them to a first blood match.
7 Mini Undertaker
When The Undertaker entered into a rivalry with JBL over the championship in 2004, it led to a match between the two at that year's SummerSlam. During the build-up to the event, JBL tried to play some mind games with The Undertaker by bringing out a mini Undertaker to mock the Deadman. He tried to tombstone the mini imposter before the real Undertaker appeared to take him out.
The Undertaker did his signature pose after fending off JBL, but the mini Undertaker got a bit carried away and tried to do the pose along with him. The Deadman had seen enough of the little imposter and gave him a huge chokeslam to end the segment.
6 Snake Pants
The Undertaker was scheduled to face Kurt Angle for the WWE Championship at Survivor Series 2000. But The Deadman had a slight mishap with his wardrobes as the airport had apparently lost some of his luggage, including the one which had his usual black leather pants.
The Undertaker had to borrow a pair of pants from his good friend The Godfather at the event. When the Deadman walked out with the confusing new attire, the fans looked perplexed as to what was going on. But the Undertaker kept going as usual and went on to compete against Kurt Angle in an unsuccessful attempt at the WWE Championship.
5 How Was Your Week?
The weeks leading up to the 2002 No Mercy PPV proved to be too much for both The Undertaker and Kane as the latter had to deal with the scandalous Katie Vick storyline, while the Deadman had to deal with the Tracy affair storyline and Brock Lesnar making things personal by threatening his wife Sara who was pregnant at the time.
The opening segment to the No Mercy PPV saw The Undertaker sitting alone in the locker room as Kane walked in and sat next to him. The Big Red Monster would hilariously ask, "So... How was your week?" with the Undertaker giving a bland reaction, hilariously pointing out the level of ordeal both of them were going through at the point.
4 The Maven Mishap
The 2002 Royal Rumble match turned chaotic when Maven pulled off the ultimate upset by eliminating The Undertaker from the match. The Deadman had his back turned against Maven as he was taunting the Hardy Boyz, which enabled Maven to carry out the deed.
However, The Undertaker made sure he made Maven pay for what he did by giving him a beat down all over the arena. The Deadman sent Maven headfirst onto a popcorn machine. He picked up some popcorn and ate it while leaving Maven writhing in pain on the ground.
3 Kurt Angle's Wig
After Kurt Angle got his head shaved after losing a hair vs. hair match against Edge at the 2002 Judgment Day PPV, he started wearing a cheap wig supported by some funny headgear to cover up his baldness. The June 13, 2002, episode of SmackDown saw The Undertaker walking into Vince McMahon's office while Angle was already in there having a conversation with the boss.
The Deadman and Angle were set to team up against Triple H and Hulk Hogan later the same night, and Vince McMahon tried to give them some pep talk. But The Undertaker looked completely distracted as he confusingly gazed at Angle's new wig on multiple occasions before finally getting to his senses.
2 Laughing At The Beast
The Undertaker and Brock Lesnar rekindled their WrestleMania 30 rivalry in time for the 2015 SummerSlam PPV. The two superstars competed in the main event of the night and took each other to their limits.
Despite all the high-octane action going on, the Undertaker and Brock Lesnar found some time to fool off with a hilarious spot during the match. Brock Lesnar did The Deadman's signature sit-up and mocked him by laughing in his face, but The Undertaker responded by hilariously laughing back at The Beast Incarnate before giving him a stiff jab to the face.
1 The Takeroonie
After the August 12, 2002, episode of Raw went off the air, the superstars present in the ring tried their hands at doing Booker T's signature spinaroonie.
The Undertaker was also in the ring during the dark segment, and the other superstars tried their best to make the Deadman do the spinaroonie. Booker T, Goldust, The Rock, Vince McMahon, and Triple H showed the Deadman how to do the maneuver, but the Deadman refused to break character at any cost and simply stood there while the others tried to convince him. While the fans almost thought they'd see The Undertaker do a spinaroonie, the Deadman, instead, gave Triple H a huge choke slam to send them home happy.