Sting’s 10 Toughest Opponents: Inside Wrestling, Holiday 1999
When readers picked up the Holiday 1999 issue of Inside Wrestling, they found one of the magazine’s most personal features in years: Sting’s own list of his 10 toughest opponents.
By late 1999, Sting had been a central figure in WCW for more than a decade. While other stars came and went — leaving for WWF or fading from the spotlight — Sting remained the franchise’s cornerstone. He was the constant presence fans associated with WCW, the face painted warrior whose feuds and friendships defined an entire era.
This article asked Sting to do something different. Instead of recounting matches or championships, he was asked to reflect: to look back on the rivals who challenged him the most, mentally and physically. These were not just opponents, but the men who shaped his career, tested his resilience, and sometimes blurred the line between friend and foe.
The piece begins by reminding readers that Sting entered the NWA in 1985, a company that would evolve into WCW. Unlike many wrestlers who changed promotions, Sting “never looked back.” That loyalty gave him the unofficial title of WCW’s “franchise.”
By 1999, WCW was in the midst of turbulent years, marked by the rise of the nWo, the dominance of Hulk Hogan, and shifting alliances among its biggest stars. Sting’s perspective mattered. Fans wanted to know not only who had beaten him or stood alongside him, but who had defined him.
Three of the first names he revealed were no surprise: Ric Flair, Hulk Hogan, and Lex Luger. Each man represented a different kind of test: Flair’s mental battles, Hogan’s psychological warfare, and Luger’s unpredictable shifts between ally and adversary.
The article is significant because it placed Sting’s words directly into print. In an age before social media or instant interviews, magazines like Inside Wrestling gave fans rare access to the personal voices of their heroes.
The feature spread is anchored by a large, striking image of Sting in his scorpion singlet, black-and-white face paint, and boots — a full-page photo announcing the theme: “Sting: My 10 Toughest Opponents.”
The layout immediately places Sting as the storyteller, and the accompanying pages deliver:
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Ric Flair – Sting calls Flair both a career-maker and a career-ender, noting that Flair was “never completely out of my mind” even during his WWF run. He credits Flair with nearly ending his career “on a number of occasions.” A photo shows Sting and Flair locked in battle inside a cage, illustrating the long, unbroken thread of their rivalry.
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Hulk Hogan – Sting admits he dreamed of facing Hogan long before Hogan ever entered WCW. But Hogan’s arrival, and eventual nWo turn, brought challenges Sting didn’t foresee. “No man affected Sting’s psyche more than Hogan,” the article states. The psychological games were so intense they kept Sting out of the ring for 15 months. A dramatic photo shows Sting and Hogan mid-battle, Hogan bleeding.
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Lex Luger – Sting describes the difficulty of categorizing Luger: “I honestly can’t tell you if being his friend is easier than being his enemy.” He notes how often Luger turned against him, making trust the central issue. Their matches were not only physically tough but mentally taxing.
The photos underscore the storytelling: Flair as the constant rival, Hogan as the psychological manipulator, Luger as the unpredictable ally-turned-enemy. The magazine pairs Sting’s voice with images that made fans relive those rivalries.
This is where Inside Wrestling excelled. It didn’t just list names or results. It gave fans insight into the mind of the star, layered with dramatic photography and narrative captions. Readers weren’t just flipping through statistics; they were reliving the emotional journey of Sting’s WCW career.
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Sting’s Loyalty to WCW – The article stresses that Sting never left for other promotions, making him the company’s “franchise.”
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Ric Flair’s Role – Flair is described as both Sting’s greatest rival and the man who defined his career’s most critical moments.
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Flair’s Mental Toughness – Sting highlights how Flair’s resilience tested him in ways few others could.
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Hogan as a Dream and Nightmare – Sting had long dreamed of facing Hogan, but Hogan’s heel turn with the nWo made the rivalry more personal and psychological.
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15 Months Out of the Ring – Hogan’s mind games drove Sting away from wrestling for over a year, a unique revelation.
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Lex Luger’s Dual Role – Friend or foe, Luger always represented conflict. Sting admits he lost count of the times Luger turned against him.
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Trust as a Theme – Sting’s reflections show how much trust — and betrayal — shaped his toughest battles.
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Cage Match Imagery – The Ric Flair photo emphasizes the brutality of their encounters.
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Hogan’s Bleeding Image – The action shot of Sting vs. Hogan captures the stakes of their feud for WCW itself.
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Personal Voice – Sting’s direct quotes make this more than a magazine profile; it’s his own reflection on his toughest tests.
For collectors today, this issue is more than paper. It’s an artifact of a turning point in wrestling history. Here’s why it holds enduring appeal:
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Sting as WCW’s Voice
Few issues give Sting such direct control of the narrative. This article is one of the clearest examples of Sting speaking to fans about his rivals and career challenges. -
Iconic Rivals Featured
Flair, Hogan, and Luger are all major names in wrestling history. Their inclusion ties this issue to three of the most significant rivalries of the 1980s and 1990s. -
Candid Sting Quotes
The feature’s strength lies in Sting’s personal reflections. These aren’t secondhand reports; they’re his words, preserved in print. -
Strong Visuals
The magazine’s full-page Sting photo and battle shots with Flair and Hogan make this issue especially collectible. -
WCW’s Legacy
As WCW neared the end of its run in the late 1990s, issues like this became snapshots of the era’s storytelling and its biggest stars.
Condition, as always, affects value. Copies with intact covers, clean spines, and no mailing labels will attract the strongest collector interest. But even well-read issues carry significance for fans of Sting and WCW’s golden era.
This feature endures because it captures Sting not as a superhero, but as a man reflecting on the battles that shaped him. Ric Flair’s constant rivalry, Hulk Hogan’s psychological edge, and Lex Luger’s unpredictable shifts are all reminders of how wrestling is as much about story and trust as it is about athleticism.
For readers in 1999, this wasn’t just nostalgia. It was Sting himself giving context to years of feuds that defined WCW. For readers today, it’s a time capsule of how Inside Wrestling brought fans closer to their heroes.
If you’re a fan of WCW, Sting, or wrestling history, the Holiday 1999 issue of Inside Wrestling is one to seek out. It’s not just a magazine; it’s a record of Sting’s voice at the height of his career.
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From Ric Flair’s cage battles to Hogan’s mind games, from Luger’s betrayals to Sting’s perseverance, this issue captures it all — with the photos and quotes that made magazines like Inside Wrestling essential to fans in the pre-digital age.
The Holiday 1999 issue of Inside Wrestling remains a prized piece of wrestling history. Its feature, “Sting: My 10 Toughest Opponents,” gave fans a rare look into the mind of WCW’s franchise player. By blending Sting’s candid words with dramatic photography, the magazine created a story that was both personal and universal.
For collectors today, this issue is a chance to revisit that story — to hold the same pages that once gave fans their clearest glimpse into Sting’s career-defining rivalries. It’s more than a magazine. It’s a preserved artifact of WCW’s most iconic era.