The 5 Best (& 5 Worst) Moments Of Raw From 1999
As time goes on, fans continue to look back on WWE’s Attitude Era with an increasingly critical eye. While the Attitude Era had the company hitting a peak in popularity with huge stars like Steve Austin and The Rock, it’s also full of “edgy” storylines and gimmicks that certainly would not fly today.
RELATED: 10 Gimmicks That Would Only Work In The Attitude Era
The year 1999 is an extremely great look at the highs and lows of WWE during this time, as there are some legitimately great moments that continue to show up in video packages today coupled with some catastrophic lows. Without further ado, let’s focus on WWE’s flagship show, Raw, and look at both the highs and lows of the program’s 1999.
10 Best: Mankind Wins The Title (1/4/1999)
WWE certainly kicked off its 1999 on a high note, as the first Raw of the year had Mankind defeating The Rock to capture his first WWE Championship. It was a huge triumph as Mankind defied the odds, with D-Generation X and Steve Austin showing up to run defense against The Corporation, who were trying to ensure the belt stays on Rocky. The moment has extra historical value, too, as rival WCW gave away the result on Monday Nitro, causing fans to change the channel to watch.
9 Worst: Terri’s Miscarriage (1/4/1999)
Hilariously, in the same episode as Foley’s victory was one of Raw’s worst moments of the year. During a random match between D-Lo Brown and Edge, Terri Runnels of the Pretty Mean Sisters -- who was (kayfabe) pregnant at the time -- attempted to interfere in the match only to slip off the ring steps, causing a miscarriage. This bizarre segment led to a forgettable storyline where Terri manipulated Brown into doing her bidding, only for it to be revealed that she was lying about the pregnancy entirely.
8 Best: Jericho Debuts (8/9/1999)
For several weeks, WWE was running hype videos counting down to someone’s big debut. Finally, on the August 9 episode of Raw, the mystery character was revealed to be Chris Jericho, who showed up to interrupt a promo by The Rock, one of the company’s biggest stars.
RELATED: 10 Things You Never Knew About Chris Jericho’s WWE Debut
WCW fans already knew Jericho as an underrated commodity in that promotion, but Y2J’s debut in WWE would really set him on the path to becoming an all-time great.
7 Worst: Gilberg Debuts (1/11/1999)
After capturing the WWE Light Heavyweight Championship from Christian in November, J.O.B. Squad member Duane Gill would soon evolve into a parody of Goldberg called Gillberg, complete with sparklers to mock the WCW star’s entrance and a losing streak instead of a winning streak. January 11th would mark his big coming out party, but the gag was already stale, considering Chris Jericho literally just did this in WCW with “Greenburg” during his abortive feud with the real deal.
6 Best: This Is Your Life (9/27/1999)
With the end of September came WWE’s highest rated segment of all time, spinning out of Mankind’s Odd Couple style tag team with The Rock. A parody of the old mid-20th century TV show This Is Your Life, the segment had Mankind honoring his tag team partner in what was a largely unscripted, incredibly hilarious promo.
Running over 20 minutes -- unheard of at the time -- Vince McMahon hated the segment, thinking that WWE was giving ratings away to WCW. But the thing was a hit and one that WWE has repeated a few times with some infamously diminishing returns.
5 Worst: Raw Is Transphobic (1/18/1999)
As Mark Henry evolved into his “Sexual Chocolate” gimmick, he entered into a feud with Chyna that that led to her calling out Henry to admit that the two of them never had sex, or else she would play an incriminating tape on the TitanTron, with Henry’s mother in attendance. Despite Henry acquiescing, Chyna spitefully played the tape anyway, which showed him getting intimate with Chyna’s friend Sammy. This caused Sexual Chocolate to find out that Sammy was actually a transvestite, and then vomiting in a toilet. It obviously hasn’t aged well but gets weird as Henry’s mom scolds and spans him on his way off stage.
4 Best: The Beer Truck (3/22/1999)
The week before Stone Cold Steve Austin’s big main event title match with The Rock at WrestleMania XV, WWE delivered one of the most iconic moments of Austin’s career as well as the whole Attitude Era. During a promo, Austin drove a “beer truck” into the arena and sprayed torrents of beer on not only his ‘Mania opponent but also Vince and Shane McMahon.
RELATED: Every Time Stone Cold Used A Vehicle, Ranked
It would be one of the most outrageous things Austin ever did -- and one that was oft-repeated even as early as two years later as Kurt Angle sprayed milk all over the WCW/ECW Alliance.
3 Worst: Beaver Cleavage: No More! (6/21/1999)
One of WWE’s more bizarre, ultimately abortive ideas -- and definitely a Vince Russo concept if there ever was one -- was “Beaver Cleavage,” a repacking of Headbanger Mosh that manifested as a series of vignettes repackaging Headbanger Mosh as a parody of Leave It To Beaver who exchanged innuendo-riddled dialogue with his mother.
When he finally debuted on the 6/21/1999 episode of Raw, Beav immediately launched into a worked shoot where he dumped the gimmick and announced himself as “Chaz,” not that that character went anywhere either.
2 Best: The Unholy Wedding (4/26/1999)
One of the big storylines of 1990 had The Corporation feuding with The Undertaker and his stable The Ministry of Darkness, which involved much terrorizing of the McMahon family. During Backlash, Undertaker kidnapped Stephanie McMahon, bringing her out the following night on Raw for a Satanic wedding during which Steph was tied to a giant Undertaker symbol in a mock crucifixion. It was a wild, outrageous segment that had ‘Taker really living up to his creepy darkness man gimmick.
1 Worst: “It Was Me, Austin” (6/7/1999)
Part of the Corporation vs. Ministry storyline involved Undertaker serving a mysterious Higher Power. By June, the two entities had merged into The Corporate Ministry and were ready to unveil their evil boss. On the 6/7 Raw, the hooded figure was revealed to be Vince McMahon, who delivered his memeworthy “IT WAS ME AUSTIN! IT WAS ME ALL ALONG!”
While the moment itself was iconic, it was a less-than-stellar reveal that made the storyline nonsensical, and proved to be one plot twist too many, even for pro wrestling, and is considered one of the big missteps of the Attitude Era.
