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WWF SmackDown Rewind: 12.16.99 – “The McMahon-Helmsley Era Kicks Off”

By Kat Bourne on 16 April 2026

Previously on the SmackDown Rewind: Armageddon 1999! Stephanie McMahon turns on her father to help her husband Triple H, Big Show successfully defends his WWF Title against Big Boss Man, and Miss Kitty wins the WWF Women’s Title in an Evening Gown Pool match.

Here’s a look at what happened at Armageddon and then Stephanie McMahon rightfully getting onto Vince on Raw for all the things he did to her during the Corporate Ministry era. Vince leaves and The Helmsleys decide to run the business in his absence.

Triple H and Stephanie McMahon-Helmsley hold a talent meeting. Vince and Shane aren’t here so they’ll be running things. Things will be handled fairly. They’re going to make it easier for those who have been held down and take the platter away from those who have had it too easily. Mankind is facing Al Snow and The Rock is facing Big Show for the WWF Title. “Tonight marks the dawning of a new era in the World Wrestling Federation, The McMahon-Helmsley Era.” Decades later, we’re about to induct Stephanie into the Hall of Fame and Triple H is probably going to say “Are you ready?” on an ESPN broadcast of WrestleMania.

Fireworks! Signs! We’re at Florida State University in Tallahassee, Florida for another taped, fan-filled edition of SmackDown. Michael Cole and Jerry Lawler are our announce team while Tony Chimel handles the ring mic.

WWF Intercontinental Championship: WWF Intercontinental Champion Chris Jericho vs Prince Albert (with WWF Hardcore Champion Big Boss Man)

Jericho tells the Boss Man to shut the hell up and wants to defend his Interchrisinental Title tonight, threatening to destroy them both “Ayatollah-style.” Albert takes up the challenge and we’re off as the music of Chyna immediately hits, walking out with WWF Women’s Champion The Kat. Jericho runs into a bicycle kick, and we zip backstage to Steph and Triple H eating fruit and drinking champagne. Stephanie tells HHH he did a great job booking this and he tells her he didn’t do it.

Jericho whips Albert into the corner and hits a bulldog as Chyna and Kat whisper to each other. Jericho tries to turn the Liontamer but Boss Man jumps on the apron, distracting them. Boss Man tosses the night stick to albert, Chyna low blows Albert, Jericho uses the night stick and gets the pin.

Chris Jericho pins Prince Albert to retain the WWF Intercontinental Title. A nothing match to continue the story of Chyna respecting Jericho.

Back to the Helmsleys. Steph promises HHH a surprise at ringside because she wants to check somebody out. “He’s cute.”

Back from break, HHH is telling Steph she can’t go anywhere and they can’t trust Test. He tells her sit down and drink champagne and she tells him he’s going. Not a lover’s quarrel.

Kurt Angle vs Test

“My Time” hits and Big Steph joins us to watch. Angle suplexes Test from behind while he’s distracted. Test grabs Angle for a spinning sidewalk slam and some words for Stephanie as she joins the commentary team. Stephanie calls Lawler out on not being supportive until now that she’s showing this new edge. “Get your cute self out of that hold,” Steph says as Angle is slammed. Test pounds on Angle in the corner with a closed fist and Steph goes to call for the bell.

Kurt Angle defeats Test by disqualification. Hey, can’t be mad at a woman that supports the rules. As with most on SmackDown, there wasn’t much to the match, but the storyline advancement is good stuff.

New Age Outlaws and X-Pac attack Test as he stalks Stephanie up the ramp. Triple H appears and smacks Test in the nose. Poor Test.

And now, the WWF Slam of the Week brought to you by the Slam Cam. Jeff Hardy tries for a Senton from the top of the cage on Raw and hits the mat.

During the break, the EMT crew tent to Test. Stephanie and HHH come up and ask them what the hell they’re doing, specifically Gerald Brisco and Pat Patterson who get thrown into a match with the Outlaws. Do it or you’re fired.

Matt Hardy vs Jeff Hardy (both with Terri)

1-800-COLLECT presents the Royal Rumble! It’s Hardy vs Hardy due to an order by the Helmsleys. Tempers flare and both Hardys lose their shirts. Jeff dropkicks Matt to the outside and follows, Matt grabbing him for a DDT on the floor. Jeff flies back onto Matt on the outside before tossing him in for a two count. Lots of battling back and forth until Jeff lands awkwardly on a top rope dive. Matt hits the Twist of Fate and gets the pin.

Matt Hardy pins Jeff Hardy. This was a good little match. Every match they have together in singles competition will not be as good, but this was enjoyable.

The Helmsleys are interrupted by Tori who is mad about being in a pudding match on Raw. She demands no more humiliation matches. Stephanie thinks she’ll face Tori tonight instead.

After break, the Helmsleys are visited by the Mean Street Posse. They learned their lesson on Monday and wish Stephanie luck in her match tonight. She has an idea for them tonight.

Tori vs Stephanie McMahon-Helmsley (with Triple H)

Kane watches on as Tori enters. Stephanie and HHH come down the aisle and Cole notes that Stephanie is still wearing a leather skirt. We see the Posse attacking Kane backstage as Tori freaks out. Tori goes to leave and Stephanie introduces her real opponent.

Tori vs X-Pac

Tori spits in X-Pac’s face, he shoves her into the corner and Bronco Busters her. X-Factor. Three count.

X-Pac pins Tori. Boo.

After break, Kane carries Tori out of the building. The Posse rejoin the Helmsleys and Triple H says they did a horrible job. Because of that, he’s giving them a rematch with the Acolytes tonight.

Al Snow is talking into the DX locker room door, saying he’ll have Mankind back there soon.

Falls Count Anywhere Match: Al Snow (with Head) vs Mankind

SmackDown is brought to you by Arizona Jeans, Western Union Money Transfer, and WWF Slam Cam. Al brings a bat in addition to Head. They battle outside and Al shatters the bat against the ring post as he misses Mankind. They brawl across the announce table and we almost lose Cole. Snow grabs a metal pan and smacks Mankind over the head with it, then does the same with a trash can lid. Cole wonders how all of this even got under the ring. Back in the ring, Snow chokes Mankind with a rope while yelling, “I’m doing this because I care.” Snow swings and misses with a street sign, Mankind smacking him on it via a double-arm DDT.

Mankind pulls out Mr. Socko and Snow dodges out of the ring and up the ramp. Snow suplexes Mankind on the steel ramp and yells at him. They brawl back in the ring again and Snow sets up Mankind in the corner before pulling out a bowling shirt and a bowling ball. Mankind grabs Al right in the snowballs with a pair of tongs and knocks Snow in the corner. He grabs the bowling ball and rolls a strike right into Snow’s pins before clotheslining him back to the outside and up to the entrance stage. They go under the Ovaltron and battle backstage. “Do you love me now, Al??” They battle into the previously seen locker room with “DX” on the door and we hear the sound of a chair smashing before Snow is tossed back out. Mankind crawls out and covers for the pin. After the pinfall, The Rock walks out with a chair and pulls the DX logo off the door to reveal his own logo.

Mankind pins Al Snow. This was a fun brawl and the twist at the end was neat.

Brisco and Patterson discuss their upcoming match. Brisco knows they could’ve beaten anyone in this business years ago while Patterson tries to talk him out of this whole deal.

Edge vs Christian

Much like the Hardys, Edge and Christian will now be punished by having to face each other. They enter to their own theme songs, the glowing orange symbol and lights mysteriously interrupting them. We cut backstage to The New Age Outlaws visiting HHH and Steph. Steph suggests that she and Triple H go get some fresh air, so the Outlaws go to work on some grapes and watch the match.

After some basic tusseling, Edge hits a nice bridge for a two count. Christian plants Edge with the Unprettier for a two, Edge tries for a powerbomb and they trade rollups. Edge calls for the spear and Christian dodges with a leg sweep. Christian rolls up Edge but Edge rolls it back up just enough for a slightly fast three count. Christian shoves the ref but raises his brother’s hand.

Edge pins Christian. This was short and they didn’t get to do much, but they did show some good chemistry and they’ll have much bigger matches to come.

The Posse are leaving with their bags when the fresh-air enjoying Triple H and Stephanie catch them. Triple H tells them to head to the ring now or they’re fired.

And now, the Lugz Boot of the Week. Bradshaw offers up some CTE chairshots on the Posse on Raw.

Acolytes Rules Handicap Match: The Acolytes (Faarooq and Bradshaw) vs The Mean Street Posse (Pete Gas, Rodney, and Joey Abs)

Faarooq gets the big Florida State welcome and gives them the Seminoles chop. We aren’t specifically told what Acolytes Rules means but it probably isn’t good for the Posse. Faarooq nails Rodney with a spinebuster and that’s all it takes. The other Posse guys are dumb and attack, getting decimated around ringside as the fans do the Seminoles chant and chop. Bradshaw grabs his trusty chair and smacks Rodney right over the head. Rough to watch in hindsight.

Faarooq pins Rodney, the Acolytes defeat the Mean Street Posse. Just the Posse humiliation match you’d expect, but the popping for Faarooq was fun.

Lilian Garcia is with Jim Ross. She asks if he’s ever experienced anything like he is now with the McMahon-Helmsley Era. He says it’s sad, he’s embarrassed for the fans and the McMahon family. His one word to describe Stephanie’s actions: “she’s acting like a little… let me say this, it rhymes with witch and it starts with a ‘B.’” Oh JR. Your decades of McMahon humiliation are just beginning.

After a break, Triple H is yelling at JR. Stephanie tells him to say what he called her and he refuses, so he gets the Stephanie Slap.

Too Cool (Scotty 2 Hotty & Grandmaster Sexay) and RIkishi Phatu vs Viscera and Hardcore & Crash Holly

A lot of super heavyweights here with Phatu, Viscera and the Hollys all in the match. I hope the ring is reinforced. Scotty hits the Centipede. Hardcore with a good delayed vertical suplex. This is all fine but despite the show being quick and breezy, it somehow also feels like we’re in hour three of SmackDown. Viscera squishes Scotty with a Samoan Drop and tosses him down with a choke. Hardcore tags back in and Scotty gets the hot tag to Rikishi, waking the crowd up as all six men battle in the ring. We end up with the two biggest men in the ring, Rikishi squashing Viscera in the corner. Hardcore gets pulled in the path of a running Viscera. Rikishi flattens Hardcore with the Bonzai Drop and our cool friends dance.

Rikishi pins Hardcore Holly, Rikishi & Too Cool defeat Viscera & The Hollys. A basic match in front of a crowd that mostly seems tired but were here for all things Rikishi.

Road Dogg tells Ass that they can’t take this lightly and have to give them the beating of their lives before laughing about it being a no DQ match.

Terri Runnels is telling Santa Claus that she shouldn’t have to tell him all the naughty things she has done because he’s seen everything. He asks for her to tell him anyway.

WWF World Tag Team Championship No Disqualification Match: WWF World Tag Team Champions The New Age Outlaws (Road Dogg & Mr. Ass) vs Gerald Brisco and Pat Patterson

Yes, Patterson and Brisco come out to “Real American” and go through the motions, Brisco ripping off his WWF Attitude shirt to reveal a Brisco Bros. Body Shop shirt. Brisco tosses power in Gunn’s eyes and the brawl is on. Patterson pulls a loaded sock out of his trunks and then a chain to smash Dogg while Brisco snaps a suplex on Gunn. Patterson hooks a Boston crab, Brisco a figure-four but Dogg flips out. Patterson smashes into the steel post and falls to the outside and Dogg puts on the brass knuckles, smashing Pat in the forehead. Ass lands the FameAsser on Brisco and that’s your pinfall.

Mr. Ass pins Gerald Brisco, The Outlaws defeat Patterson & Brisco to retain the WWF World Tag Team Championship. This was mostly nothing but at least Patterson and Brisco aren’t in evening gowns.

And now the WWF Smack of the Night presented by Western Union Money Transfer: Stephanie slaps JR.

WWF Championship Lumberjack Match: WWF Champion The Big Show vs The Rock

“My Time” plays for the 38th time tonight and Triple H and Stephanie head out to the stage that just happens to have a recliner and table on it. HHH: “This title match just happens to be a lumberjack match.” The heel side come out to lumberjack, including DX, Dudley Boyz, Viscera, Prince Albert, Mideon, Kurt Angle, The Hollys, Al Snow, and the Mean Street Posse. Cole does not like the way that this smells.

Rock starts off with the rights in the corner, Show whips him into the corner for a chop. Rock gets tossed outside and the lumberjacks smack him around before tossing him back in. Rock knocks Show out and the same happens to him. Rock tries for a cover and DX pops on the apron to be hit down. Rock hits a Rock Bottom on Show, Gunn pulls Rock out and the lumberjacks beat him down again. Show chokeslams Rock and covers, Gunn and X-Pac pull Show outside and they stomp away. Rock clotheslines himself and Show outside and again, lumberjack attack. Rinse and repeat.

Mankind wheels his plundah cart out starts smashing heads with a trash can. Show and Rock grab some weapons and swing away as well as things break down into a huge brawl all over the ring and ringside area. HHH and Stephanie give us disgust as Rock hits Viscera with a Rock Bottom and People’s Elbow. Rock’s music plays so the match was called at some point in all this.

The Rock and Big Show wrestle to a no contest, Big Show retains the WWF Championship. The was all story, but the brawl was fun.

So, this was the SmackDown beginning of the McMahon-Helmsley Era. It was largely the McMahon-Helmsley humiliation ritual show, causing partners to wrestle each other and guys and girls who have wronged them into bad situations. It wasn’t entertaining as much as a trainwreck, but I’m intrigued to see where it goes next week.

Next week: Rock and Snow in a cage! Mankind gets a WWF Title shot! Kaientai!

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