10: Mini-Undertaker

When The Undertaker reverted to his Deadman persona in 2004, any comedic elements of the character were virtually abolished. However, there was one segment which was comedic in nature, and could have impacted the credibility of The Deadman’s persona.

During The Undertaker’s WWE Title feud with JBL, JBL would call out The Deadman, only for a mini version of The Undertaker to surface. This comedic segment turned serious when the real Undertaker appeared to save the day.

In a bizarre yet comical moment, the mini-version of The Undertaker decided to perform The Undertaker’s signature pose alongside the real Undertaker, and this hilariously led to the mini-Undertaker receiving a chokeslam.

Some fans online at the time were critical of the segment, as they believed that this version of The Undertaker being involved in comedy of any kind was detrimental, yet there was a portion of the fan-base who believed the segment to be harmless fun.

9: How Was Your Week?

The 2002 No Mercy PPV kicked off with a rare cold-open. In the cold-open, The Undertaker was seen sitting in the locker room, getting ready for his Hell in a Cell showdown with Brock Lesnar. This was when his half-brother Kane came in, sat down next to him, and hilariously stated: “so, how was your week?”.

The Undertaker then pulled a rather humorous facial expression, as the fans in attendance laughed. Both members of The Brothers of Destruction had been through hell over the past 7-days, so it was indeed an appropriate comment to make from Kane, and it was unusual to see two serious characters involved in a tongue-in-cheek segment.

8: Buckle Up Teddy

At the Breaking Point PPV in 2009, WWE (yet again) decided to replicate the Montreal Screwjob from 1997. In the show’s main event, World Champion, CM Punk would tap out to The Undertaker’s Hell's Gate, and this was when SmackDown GM, Teddy Long informed The Deadman that the Hell’s Gate was banned.

Long ordered the match to continue, and when the bell rang once again, Punk locked in the Anaconda Vise, and the bell rang, despite The Deadman failing to tap.

On the following edition of SmackDown, Long would enter into a limo in the parking lot, and it was revealed that The Deadman was in the driver’s seat, and The Undertaker declared “Buckle Up Teddy” in one of the most unintentionally funny moments in SmackDown history.

It’s unknown if the segment was supposed to be corny, yet it certainly wasn’t helped that Long did the most laughable audible gasp in existence, and the Buckle Up Teddy segment is still often used for comedic memes.

The storyline between The Deadman and Long didn’t really go anywhere meaningful. It was evident that WWE needed a way to keep the World Title on Punk, whilst keeping The Undertaker credible, and a poor and cheap replica of the Montreal Screwjob was the only way WWE could think of achieving this.

7: Those Pants…

It’s been the belief for the past two-decades that The Undertaker wore hideous snake-skin pants at the 2000 Survivor Series, as his original planned gear was lost. The Undertaker at the aforementioned show would collide with Kurt Angle for the WWE Title, and although this should have been a huge PPV match, all fans could focus on was The Deadman’s revolting attire.

On his Six Feet Under podcast, The Deadman went into detail as to why he decided to wear the pants at the PPV, and The Undertaker discussed a conversation he had with the woman who made his ring gear:

“I remember going to her, I’m the American Badass at this point. I go to her because she was like, ‘Hey, what do you want to do for Survivor Series?’ I said, ‘I want to do python skin pants.’ She looks at me, deadpan, ‘No you don’t.’ ‘They will be badass. Think about it. Snakeskin pants.’ ‘Mark, no.’ ‘Are you kidding me?’ I thought she would love the idea. ‘You’re too big. They will look ridiculous.’ ‘Noooo, this is going to be the absolute coolest look the American Badass has ever presented.’ ‘No, Mark, it’s not.’”

The Undertaker continued by saying:

“She tried her hardest to talk me out of those pants, and I wouldn’t hear it. Then, it got to the day of. I didn’t have any backup. When I put them on and I looked. I was like, ‘Holy s**t, you’re the main event tonight against Kurt Angle and you look like you have some pants that belong to the Godfather.’”

The Undertaker would thankfully never wear the dreaded pants again on WWE TV.

6: The Undertaker’s Hood Gets Stuck

Not every corny moment is going to be a wrestler’s fault, and this was the case when The Undertaker appeared at the special RAW 1000 show in 2012.

The Undertaker would stand side by side with his half-brother, Kane and the duo would dispatch a number of lower card heels. The segment was entertaining, yet before the physicality ensued, The Deadman suffered a huge wardrobe malfunction.

When The Undertaker went to flick his hood off during his entrance, his hood awkwardly remained stuck on his head. The Deadman then looked completely ridiculous trying to get the hood off his head.

The WWE Hall of Famer would reflect on the blunder during an appearance on Dallas Morning News:

“….Our opponents made their entrance, Kane makes his entrance, I make my entrance. As I go to take my coat off, the coat folds. It basically gets stuck on my mitts, my MMA mitts. The more I tug to try get out of them, the tighter it gets. Because the leather on this coat was really thick. I can’t get out of this coat, right? It’s Monday Night RAW, it’s live TV….”

5: Motorcycle Mishap

Vengeance in 2003 was a stacked event, and it was also notable for being SmackDown’s first-ever brand exclusive offering.

One of the top matches on the card was The Undertaker vs. John Cena, and when The Deadman was making his entrance using his trusted motorcycle, something went wrong, and this forced The Deadman to improvise on the spot.

In an awkward moment – The Undertaker’s bike stalled, and it took The Undertaker a few seconds to gather himself together, and in the end, The Deadman ultimately decided to take a leisurely stroll to the ring.

Every wrestler would have looked corny in this exact moment, and The Undertaker handled it in the best manner imaginable.

4: The Undertaker Makes Kane Break Character

In November 2006, The Brothers of Destruction teamed up on SmackDown to take on the duo of MVP and Mr Kennedy.

At one point in the match, The Undertaker looked to follow up a Snake Eyes on Kennedy with a trademark big boot, but before he could finish his planned spot, Kane entered the action, and delivered his own devastating big boot. The Deadman looked at his younger brother as to say “what the hell?”, and The Undertaker’s facial expressions were so funny, that Kane started to laugh in the middle of the match.

Even Michael Cole and JBL on commentary found great humour in what they were watching, as both were struggling to keep it together, and JBL justified the comedic spot by claiming that both men were trying to outdo each other.

3: Blood Does What?!

For the most part, during his legendary career, The Undertaker managed to deliver a promo without it creeping into the cringe territory. However, during a now infamous promo in 2001, The Deadman left everyone confused and disgusted.

On the January 29 edition of RAW, The Deadman along with Kane cut a backstage promo, which focused on Rikishi and Haku, who The Brothers of Destruction would be taking on in a First Blood matchup on that week’s SmackDown.

In the promo, The Undertaker would boldly declare that blood “turns him on”. If this wasn’t weird enough, The Deadman would then state that making other’s bleed turns him on even more.

The line was supposed to be serious rather than humorous, yet the delivery was so outlandish that it was hard to take the promo seriously.

2: The Deadman’s Hilarious Laugh

The 2015 SummerSlam event was main evented by a WrestleMania 30 rematch between The Undertaker and Brock Lesnar. The match was 100 times better than the WrestleMania encounter, and the two delivered a match that had great storytelling, compelling action, and moments that would later turn into memes.

One of the most memorable moments in the match saw Brock Lesnar sit up and begin to laugh at The Deadman. The Undertaker then performed his signature sit-up, and he imitated Lesnar’s laugh. Was it corny? Absolutely, but it was amazing to see The Deadman let himself go in this manner and show a side to him that was rarely ever presented in WWE.

1: The Taker-Roonie?!

Often after RAW or SmackDown has gone off the air, the WWE talent likes to improvise, and deliver something memorable for the fans.

In 2002, after an episode of RAW, numerous names including The Undertaker, The Rock, Triple H, Booker T, and Vince McMahon were in the ring, and they were all taking turns delivering a Spinaroonie. However, when it came time for The Phenom to perform the trademark spin, he just couldn’t bring himself to break character.

The segment, which is available to watch via YouTube is a glimpse at how vital The Undertaker believed staying in character truly was, and it’s apparent that there are moments during the segment, in which the legend himself debates whether to commit to doing the spot.

According to The Undertaker during an interview with Chris Van Vliet, the Spinaroonie is the one thing he refused to do whilst in WWE:

"I always told him [Vince McMahon], 'I don't care who you are, what you do, you'll never get me to do that.' And you don't tell Vince that you can't or won't do something, because it becomes his passion in life. But I can honestly say he never got me to do a Takeroonie. So, I won. That's the one battle I won with Vince."

‍