#87 – Royal Rumble 1999

We take a long look at a classic WWF attitude pay-per-view featuring one of the greatest WWF title matches of all time, a classic Royal Rumble starring the man himself, Vincent Kennedy McMahon, and a crapper of an undercard filled with Degeneration-X and the Corporation. Please support the podcast by visiting flairchop.com where you can buy our tremendous “mail-order wrestling gimmicks” t-shirt, posters, and the box set of our first 50 episodes. You can also get a free OSWP sticker by leaving a comment on the iTunes store.

This episode has been archived. It is available either by ordering the physical “OSWP Season 3 box set” with episodes 76-100 or it can be instantly downloaded in a digital version of the “OSWP Season 3 complete set” with episodes of 76-100. The physical box set will always be our favorite, as it comes with a full color booklet featuring art by our friend Dean Stahl and looks great on your bookshelf next to your coliseum home videos. The instant digital download version also comes with high resolution PDFs of the booklet that you can view on your computer. Both the physical box set and the digital download come with two bonus episodes featuring our reviews of the Clash of the Champions 9 and the Royal Rumble 1988. These episodes have never been available on flairchop.com. But if you only want to hear this one episode, we also offer the option of instantly downloading just the individual episode for a small price.

This episode has been archived in the Season 3 digital box set available for $9.99 at the OSWP Merch Store!


  1. Irrestable object says:

    Gangrel was an awesome character. To confirm your points. Gangrel started in UWF as one of the black hearts. He the starting using the vampire gimmick and called himself “lastat”. Inspired by interview with a vampire.
    He was let go by the WWF for weight issues. He is also married to Luna Vachon….. Could you imagine what their kids Look like??

    Great show Guys!! Totally Tits!

  2. Butt Douglas says:

    I still play the X-Pac song (YEXXX PYEAAACCCKK) song when I’m driving to the corner to buy some Surge. Sometimes the Juggalos give me trouble, but I just give them the crotch chop and drove over to my buddy Johnny the Maniac’s house to watch his South Park episodes that he taped on to his VHS. Have you guys seen that show?

  3. Tim F. says:

    MACGRUBER!!!! I’m going to agree that MacGruber is an awesome movie. I was, however, disappointed ******spoiler alert****** when all the WWE stars blew up.

    Anyway, I’m listening to the commentary while posting this (Road Dogg just bit Boss Man’s nose, a key point you guys forgot to cover, haha), and holy cow, the crowd is going nuts despite the fact the these undercard matches are pretty pathetic. Just makes me miss how exciting/over wrestling was back then.

    Thanks for bringing back all these memories.

    I won’t lie, I was hoping this episode would be dedicated to Royal Rumble ’94. Of course that’s only because I thought Chuck Norris was part of the Casket Match. After doing some Wikipedia research, I now know that Chuck Norris was part of Survivor Series ’94 due to the shenanigans that took place during the 94 rumble casket match. Hopefully you guys will review that soon?

    I look forward to whatever you review next. Always a good listen.

  4. brick says:

    before listening to your podcast I decided to watch the event my self and do my own review .
    Match # 1
    (9)Road dogg Jesse james vs. big boss man
    Death list member # 1 big boss man
    First of all I sang along with the road dogg’s intruduction . The match seemed to be power vs. speed with the boss man using power moves a and the road dogg going for quick attacks . The match ended with the boss man side slam to win the match but not the title

    Match # 2
    championship match
    # (1)Ken shamrock vs. #(7)bad ass Billy gunn

    Ken shamrock was very for most of this match with Mr. ass able to survive the attacks
    When Val venis runs into the ring and attack ken shamrock .
    The match ends when billy gunn miss a dive off the top rope and ken shamrock got the match by submission .
    I expected ken shamrock to not let go and get disqualified but let go just before he would have been stripped of the title

    Billy gun had submitted to mankind June 16 1998 Monday raw tapings

    Match # 3
    European championship
    Gengrel vs.(6) x Pac
    X pac began the match on a sugar high
    Quick match and finally generation x gets a victory tonight when x pac gets the victory with the x factor
    Match # 4
    Woman’s championship
    Luna vachon vs. sable In a strap match
    Did any actually think that sable would forfeit the belt live on the pay per view .
    Again one wrestler would be dragging the other touching the turnbuckle but the other one is touching it as well .
    I can’t remember who it was in red sweater and blue jeans that attacked Luna in the match in order to for sable to gain the victory

    Death list member # 2
    Luna vachon

    Match # 5
    Wwf championship in a I quit match
    (2) The rock vs. ©mankind
    I think they spent to much time asking the opponent if they quit or not . Instead of just beating up there opponent so bad that they have no choice to say I quit.
    I though they were both crazy when they climbed the later to get to the crowd .
    I thought this match was to tame at first but I got better as the match went on .
    Of course they use mankind’s interview to make it look like he says I quit .
    Mankind is the only one to get a rematch for the title

    Royal rumble match
    First off all if you go out though the ropes then you should have to get back in before a ten count or at least before a 20 count to stay in the match .
    Lets see the match
    (5) Steve Austin and Vince McMahon are the first 2 in the ring .
    They both should be counted out when they leave the ring and head to the ladies wash room .
    Golga is next in the ring and get eliminated before Austin and vince decide to do there little chase .
    Dross is next in the ring followed by edge
    Gill berg made in entrance and exit in a hurry . Any one realize gill berg was the light heavy weight champion at that time but never defended it .
    Steve Blackman ,Dan severn , tiger ali Singh , blue Melanie fill up the ring until mabel comes in and clears 5 men from the ring until him and road dogg are the only two in the ring .then they waste more time by showing us that mabel is going to sacrificed by the undertaker and the a.p.a.
    Leaving the road dogg all alone in the ring until gangrel enters and exits Kurrgan, al snow comes in is thrown over Kurrgan to be eliminated
    Goldust ,godfather ,Kane enter the ring
    Kane then cleans house then kane eliminates himself from the rumble
    Mr. McMahon then returns to the ring the sits down at the broadcast table .
    While ken shamrock waits in the ring (7)billy gunn come next for two minute rematch from early tonight test enters the ring . And stone cold then returns to the ring and eliminates ken shamrock Triple h is next in the ring
    When did the boss man enter the match .
    Val venis enters and billy gunn leaves
    (6) X Pac, mark Henry ,Jeff Jarrett then enters the ring causing it to be crowded d lo brown is next
    Test ,x pac ,jeff Jarrett are eliminated from the match
    Leaving owen hart Austin ,d lo brown ,mark henry triple h ,big boss man and val venis and or yeah chyna comes in to the ring
    Mark henry and chyna are the next 2 to go .
    We end up with d lo brown , big boss man stone cold and owen hart .
    Owen hart and d lo brown are eliminated which means that the boss man should be the winner but of course he is not since there is no count out and stone cold throws him over the top rope .
    Mr. McMahan flukes out a victory . When the rock comes down to the ring side .

    Death list # 3 golga
    Death list # 4 Owen hart
    Death list # 5 test

  5. I had a froot of a time listening to #OSWP87 at work last week. Thanks gentlemen!

    About the comment that the Royal Rumble 1999 hosting one of the best WWF Championship matches, I have to agree. Nowadays I tend to have a tough time watching all the chair shots to the head, having the knowledge that’s out there about concussions but both Foley and the Rock tell an awesome story in this “I Quit” match that we don’t see in the WWE in 2013.

    The Royal Rumble match from 1999 tells an awesome story from start to finish and rarely stays within the 20×20 box we call a ring. I was pissed off too when I first heard that Mr. McMahon won the Rumble but seeing the story play through WrestleMania XV, McMahon winning was the best possible guy to win.

    I always found it odd that the Undertaker wasn’t a part of the Rumble card other taking Mable and moving him one step closer to Big Daddy V. Maybe it was the Dead Man’s way for payback when Mable injured his face via a leg drop, when, in 1995?

    I felt that a better way to turn Mable to the dark side would of been if the Undertaker was in the Rumble match and eliminated Mable and then eliminated himself and chased him down, indicating that “we cannot out-run the devil.” Just a random thought.

    Anyways, thanks for covering this awesome Rumble card, even though the first few matches blew a major DX crotch chop.

  6. I must say, that while most people crap on the undercard at this time, I loved it. All these guys were over too. I LOVE LOVE LOVED Gangrel. He replied to a recent tweet with a “lol” and I treasure that tweet. I also got a reply to a tweet by Michael McGillicutty. The great part? I didn’t @ him in said tweet. The man is searching Twitter for his own name. Worked for me, I now follow him.

    And of course, the great D’Lo Brown! Gangrel and D’Lo Brown were my two favorites at this time, with Mankind a close third. And The Undertaker’s Ministry of Darkness was (in my humble opinion – mind you an opinion that has been replied to by Gangrel and Michael McGillicutty, as well as retweeted by Jim Ross and Gene Snitksy) the greatest faction of all time. I just loved the whole demonic gimmick, and I believe this was the time where Paul Bearer started wearing devil red suits. My favorite Undertaker of all time (Booger Red Undertaker being my least favorite). Maybe greatest is too strong, my favorite faction for sure.

    I still remember watching the Rock/Mankind match and thinking to myself “That’s a tape of Mankind’s promo earlier!!!!!” Not sure if they ever followed up on that, or if they played it because Mick was most likely unconscious.

    While that was a great match, I still think the 2000 Rumble match between Cactus and HHH was one of the best title matches I have ever seen. Considering at times they use the Rumble to feature crap title matches (think Lesnar vs HARDCORE HOLLY and Orton vs Jeff Hardy), this was a great all time title match, and probably the greatest Rumble title match.

    • OH! And Val Venis interfered in the Shamrock/Ass match because he had recently started dating Shamrock’s sister Ryan. I guess everyone was trying to get with Ken Wayne Shamrock’s sister.

  7. Was Ed O’Neil the spokesman for 1-800-Collect in the commercials? I wonder what he’s up to these days? 🙂

    I am also fortunate to never have taken the Cat’s Cradle. The Cat’s Cradle and Boss Man Slam have a slight difference though in that the victim’s head is facing the opposite direction.

    Dre, which catchphrase did you trade Disco Stu a Mick Foley action figure for?

    I wasn’t a fan of the Insane Clown Posse, but from listening to a wrestling related interview with them, they sound like they’re true fans. I guess they didn’t get paid a dime during their short WWF run with the Oddities. They just wanted WWF to play commercials for their CDs, which never happened. So one time when they were booked to go out and get killed, they just walked out the back door and never looked back.

    At the very end of the podcast, I was almost expecting you guys to splice in “Number 9” between each time Jook said “Dre”.

    • In Dre’s defense, I was listening to an Art of Wrestling Podcast, and Colt Cabana pronounced Kurrgan “Kurr-a-gan” with three syllables.

  8. jackie crockett's library card says:

    I only vaguely remember this PPV, with the exception of the title match and the rumble. It seems that I’m fortunate in that respect. I have a list that I jotted down while listening so here goes.
    • Bossman always ran the ropes. Yes he was a fatty, but he could still go. Unfortunately, bossman did nothing for me then, does nothing now. Roaddog was so over at that time it was insane. He is the perfect example of what good charisma can do for a no physic and limited ability midcard guy.
    • Mr. Ass is the perfect partner for Roaddog because he has no charisma and limited ability but had a million dollar look (and that dude’s a giant). His theme song lyrics are “I love to love ‘em, I love to kick ‘em, I love to shove ‘em, I love to stick ‘em (sorry Blackcat, Dre you are correct). One of my favorite absurd theme songs.
    • This undercard sucked. I always felt that WWF at the time had a good variety to the roster and yet the undercard was often boring compared to WCW. Although by this time that was beginning to shift.
    • Gangrel was a great character. Entrance was so good and yet they never did anything with him. I always attribute a lot of this to the Russo factor. Russo had a knack for creating these characters that got over really fast( i.e. Val Venis, The Godfather, and sexual Chocolate Mark Henry) but then had no where for them to go. It’s too bad.
    • I would love for Dre to sing a full version of X Pac’s entrance.
    • No one on the undercard in late 90’s where’s trunks or tights, everyone where’s street clothes or PJ’s. Also everyone wore sunglasses to the ring.
    • I couldn’t stand Sable, her mike work was worse than her ring work and that’s not saying much.
    • The Oddities were part of the Factionpallooza era of WWF. Everyone was in a faction it seemed like.
    That’s all I got, great show as always guys.

  9. Switchblade Robinson says:

    You know why I watch pro wrestling and not UFC? CUZ IT’S FAKE! Listening to you guys describe the chair shots made me ill. I was in my late teens in the late 90’s, loved ECW and the Attitude era in WWF. I completely respect the guys who put their bodies on the line but it’s supposed to be a work when it’s all over.

    And of course my favorite wrestlers are Foley, Sabu, RVD, New Jack and many of the ECW crew from that time so I am a complete hypocrite. I loved their matches, just hope they don’t pay for it with Parkinson’s or something worse.

    Great episode!

  10. "Oh, you didn't know!?!" says:

    Dre is right, Macgruber is an incredible movie.

  11. A Paul heyman guy says:

    Listening to this episode reminded me of the good ole days of wrestling & how it will never be the same. Don’t get me wrong there are good characters & wrestlers today like ziggler, sandow, punk, & Daniel Bryan but those guys on their best days couldn’t hold a candle to stone cold, the rock, or even Vince McMahon. I totally forgot how big of a jerk Vince was & how he was such a great heal. I too was shocked how jacked Vince was & with lawler doing commentary just put it over the top. I wish Vince would come back but too bad his idiotic son in law Is going to drive this company into the ground. I also agree with you guys this is probably the second best rumble just because nobody thought Vince was going to win. Love the show & keep up the great work

  12. Tough as Nails says:

    The visual of Black Cat walking like Vince to a meeting with No Chance in Hell playing is awesome. Do you do the wobbly leg/detached shoulder thing he does? Not sure how he doesn’t blow out both his knees everytime he walks like that. I wouldn’t last 4 steps and I’m half his age!