The Undertaker Out-Parties Cypress Hill: A Legendary Night on Tour

The Undertaker, WWE's iconic "Dead Man," has created a second career from telling stories from the road. Before he started doing his one (dead) man shows around big WWE events, Taker had a candid conversation on The Broken Skull Sessions with Steve Austin a few years ago, where he recounted a memorable night where he outlasted the legendary rap group Cypress Hill during a European tour.​

A Night Off Turns Into a Challenge

During a grueling 17-day tour, The Undertaker decided to take a rare night off to recharge for upcoming shows in cities like Amsterdam and Berlin. However, his plan took a detour when he encountered his fellow wrestlers and members of Cypress Hill at the hotel bar.​

As he prepared to retire for the evening, the group called him over, leading to a friendly challenge about his partying stamina. Not one to back down, The Undertaker accepted the implicit dare, setting the stage for an unforgettable night.​

Outlasting the Legends

The evening unfolded with The Undertaker matching Cypress Hill drink for drink. As the night progressed, one by one, the members of the rap group called it quits, leaving The Dead Man as the last one standing. This feat added another chapter to his storied career, showcasing his endurance both inside and outside the ring.​

Reflections on the Rock 'n' Wrestling Lifestyle

Reflecting on that era, The Undertaker acknowledged the rampant partying culture in professional wrestling, noting that the excesses rivaled those of rock stars. His ability to outlast renowned party enthusiasts like Cypress Hill became part of his legendary persona, blending the worlds of wrestling and music in unexpected ways.​

This anecdote offers a glimpse into the larger-than-life experiences that define wrestling lore, highlighting the camaraderie and challenges that come with life on the road.

Here's the full quote, transcribed by Ringside News:

“I think it was pretty commonly known back then that I burnt the midnight oil. I wasn’t always first, but there was always that comradely with the guys I really enjoyed. It had a lot to do with drinking whiskey, hanging out, and telling stories like we all do. Any time we get together we’re telling stories.”

“So this was in the back side of probably a 17 day tour and I’m like ‘Alright guys, look I’ve been going hard every night I’m gonna stay in. I’m gonna take a break, we’ve still got three or four days left.’ I had to pace myself. One day out of 17 I was gonna take off.”

“We had Amsterdam and Berlin and all these places coming up I wanted to be fresh and ready to go, right? I get to my room and I go I’m gonna go to the bar and say hello to everybody and the I’m gonna go to my room, I’m gonna go to bed. So I go strolling in the bar, I’ve still got my bags — ‘Take! Take! Take! Take!’ someone’s screaming, you know ‘Come here, Take, come over here!’ It was our guys, but then it was some of the guys from Cypress Hill. They were on tour over there, ‘Hey guys what’s going on,’ you know?”

“I’m being polite, asking them tour questions and all that and then it was like, ‘Okay man I’m gonna head down the road, you know?’ Then I turned around and I heard, ‘Oh man I heard you could party!’ It was like I turned around and said ‘Yeah, I’ve been going pretty good,’ you know.”

“Then somebody else mouthed off and it was like, ‘Okay, I’m staying.’ Somebody smarted off a little, they had no ill will, but it was a moment and that’s how it was sometimes I get, ‘You probably shouldn’t have said that.'”

“So here we go and we drank all the whiskey. So we close the bar down and there’s still people standing upright, right? So I don’t know how I ended up, it was me and X-Pac and we ended up in one of the guys’ [from Cypress Hill] rooms and they’re known for their cannabis intake, you know that’s never been my deal, but I remember sitting in this room with people I didn’t really know and there was this haze kinda like the fog had some and sit down at a different level, right? I’m sitting at the desk and I’m looking around and there are probably only two people that are upright and there are like bodies laid out everywhere and I turned to say something to X-Pac and X-Pac is asleep on my shoulder, right?”

“I gave X-Pac the nudge and he’s like, ‘What up, Take?” like he’s been there the whole time, right? I said, ‘Kid, I think our work here’s done.’ He went, ‘Oh, okay alright.’ So, I pick him up, the door opens and a big plume of smoke falls out into the hallway, it’s like the gunfight at the OK Corral, believe me, I was feeling it.”

“I remember coming down the next day and I felt bad the next morning. We had an early call and I’m telling myself ‘You’re gonna go down there and be cool,’ but my head’s pounding and I go down there and I’m like ‘Hey guys’ and they’re still trying to call guys to get them out of their rooms and I’m just no-selling it.”