Two years ago, I wrote about one of my more memorable summertime memories. I wrote a fairly deep dive into one of the wildest celebrity crossovers of the Monday Night Wars: When Jay Leno stepped into the wrestling ring at WCW's Road Wild 1998.
I'm reposting it this week because that whole nWo invasion of The Tonight Show (and Leno actually wrestling!) still makes me smile and takes me straight back to those peak wrestling summers of the 90s.
The late 90s were absolute peak pro wrestling; I'll hear no arguments from "the kids today" trying to claim their flipping and flopping is better. Sure, it may be more athletic, but the fervor and excitement created by the weekly pop culture collisions that were The Monday Night War will never be matched. Summers meant no school, backyard matches with friends, N64 games like WCW Revenge, and obsessively checking Prodigy wrestling message boards late into the night after Nitro.
WCW was throwing everything at the wall with celebrity angles to keep up with the rising stars of the WWF, like Stone Cold Steve Austin and The Rock, while celebrities like Dennis Rodman, Karl Malone, and Jay Leno kept eyes on WCW.
I loved the build-up of the nWo crashing Leno’s set, the fake Hulk Hogan bit, and Leno playing it totally straight. Then at Road Wild in Sturgis, Leno teamed with Diamond Dallas Page against Hulk Hogan and Eric Bischoff in what will never be called a technical masterpiece, but for 14-year-old me it was pure entertainment. I, of course, missed it live because we were on vacation, but it was still just as awesome reading about it in the newspaper the next day.
If you were a wrestling fan during the Monday Night Wars, this one’s a fun time capsule of just how crazy (and fun!) things got. Read the full article HERE!
What was your favorite celebrity wrestling moment from that era? Leno? Rodman? Mike Tyson? Drop it in the comments!

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