updates | March 27, 2026

10 Things Fans Should Know About The Undertaker's Time In WCW

The Undertaker is an all-time WWE legend. After a career with the company which spanned three decades (with him still being a part of the promotion post-retirement), he feels synonymous with Vince McMahon’s professional wrestling empire. However, he wasn’t always under the WWE banner, with him in fact initially wrestling in WCW.

RELATED: 5 Biggest Allies Of The Undertaker's Wrestling Career (& 5 Biggest Enemies)

It does seem strange that someone who would become so loyal to WWE would once be a part of their biggest rival, but he was in fact a wrestler there for a little while. There are certain things that fans should know about The Undertaker’s time in WCW, with it being quite different from his WWE career in every way.

10 Terry Funk Gave Him His Name

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Before Mark Calaway became renowned the world over as “The Undertaker”, he first wrestled under other ring names. Texas Red, Master Of Pain, and The Punisher made up his first few names, but when he came to WCW he became “Mean” Mark Callous.

It was the legendary Terry Funk who would don The Undertaker with this name, which he revealed in his book - Terry Funk: More Than Just Hardcore. It was a nice play on The Undertaker’s real name, making him feel intimidating but also fitting in with the slightly goofy names of that era.

9 Loves Pet Snakes & Ozzy Osbourne

Ozzy Osbourne WWE

The Undertaker’s early gimmick in WCW wasn’t overly well-thought-out, and the commentary from WCW’s Jim Ross when describing his character will show just how vague the ideas were for “Mean” Mark Callous.

On the commentary desk, JR’s description stated that he was someone who loved having pet snakes and enjoyed the music of Ozzy Osbourne. Whilst this was a fairly decent way to gauge the vague type of character he was, it wasn’t enough to make him stand out.

8 Replaced Sid Vicious

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The Undertaker’s first foray into WCW saw him enter The Skyscrapers tag team alongside Dan Spivey. The Undertaker wasn’t the first man to be in this duo, with him in actual fact stepping in for the injured Sid Vicious (someone he would later go on to main event WrestleMania against).

The Skyscrapers were a dominant duo, going undefeated until Sid’s injury. When Undertaker stepped in to fill the hole, the pair weren’t as successful as the original act, likely due to Undertaker being a less prominent name at the time.

7 The Masked Skyscraper

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The Skyscrapers tag team was cursed. After Undertaker and his partner Dan Spivey were finally getting some steam in WCW with victories and a feud with the legendary Road Warriors, whom they attacked and ambushed at Clash of the Champions, the team was dealt with another blow.

RELATED: 10 WCW Wrestlers Who Were Completely Unprepared For The Spotlight

The Undertaker was set for the biggest match of his career against the Road Warriors at WrestleWar in a Street Fight, but Spivey left WCW days prior. This meant that a masked Blake Beverly stepped into the role of the “Masked Skyscraper”. The original team was now completely unrecognizable, and this alliance lasted just one match.

6 Excursion To NJPW

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It was very common for WCW names in this era to take an excursion over to NJPW or elsewhere to gain some experience and for a refresh, and that was exactly what happened with The Undertaker following his stint in The Skyscrapers tag team in 1990.

Wrestling as “Punisher Dice Morgan”, The Undertaker mixed it up in the ring with names such as Masahiro Chono, Masa Saito, Shinya Hashimoto, Scott Hall, Bam Bam Bigelow, and more, no doubt gaining vital experience.

5 Paul Heyman Guy

Paul Dangerously And Mean Mark Callous Cropped

When The Undertaker returned from NJPW, he was repackaged as a dominant singles competitor, and he was given a manager to help him along - none other than Paul E. Dangerously, later known as Paul Heyman. It’s true, The Undertaker was at one stage a Paul Heyman guy before it was even cool!

This no doubt gave The Undertaker some momentum given the talents of Heyman on the microphone, though the alliance was unfortunately fairly short-lived and didn’t really go anywhere in the long-term.

4 First PPV Singles Match Against John Laurinaitis

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Whilst The Undertaker’s first PPV match came against the Road Warriors, his first singles match on a PPV came a little later on, and it was against another recognizable name - Johnny Ace aka John Laurinaitis.

Under the shortened name of just “Mean Mark”, The Undertaker defeated Laurinaitis at Capital Combat 1990 in a little over 10 minutes. This was designed as an extended squash to make the young star look good, and whilst it did its job, it wasn’t anything special.

3 Challenged For The United States Championship

Callous Luger

WCW saw the first time that The Undertaker had ever challenged for a title in wrestling, and it was the historic United States Championship that he first targeted - with him even challenging for the gold on PPV.

He stepped up to iconic champion Lex Luger, who is still to this day the longest reigning United States Champion of all time, in a losing effort at the 1990 Great American Bash event.

2 Heat With Ole Anderson

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On paper, it seemed as though The Undertaker was making a gradual climb up the card in WCW, and with good in-ring talents and a domineering size, it seemed like he was ready-made to be a star. However, WCW booker Ole Anderson didn’t believe this was the case.

RELATED: 5 Great WCW Debuts That Led To Awesome Careers (& 5 That Led To Bad Careers)

Ole Anderson is renowned for saying that The Undertaker would never draw a dime outside WCW. Jim Ross on his Grilling JR podcast, he explained how he liked Undertaker, but clearly others didn’t see what he did; I always thought he had everything. He’s 6’9″, athletic, and tough, durable. Just hadn’t had the right gimmick. And sometimes when you’re like Ole didn’t like him. I don’t know why.” (H/T 411Mania)

1 Dream Match Vs. Sting

Callous Sting

For many years, fans clamored for a dream match between two all-time icons in Sting and The Undertaker, and even when WWE had the chance to pull the trigger, they didn’t go through with it.

However, back in WCW, this match actually happened. In fact, it happened in The Undertaker’s final ever WCW match in late 1990 on a house show when he challenged Sting for the NWA World Heavyweight Championship, though only a few people saw it.