Big Boss Man’s Best Moments and Memorable Matches
WWF Saturday Night’s Main Event — May 1989
Featuring the trademark blue steel cage of the era, the Boss Man would bring his handcuffs into play in his attempt to vanquish Hulkamania. This stood as the Boss Man’s first true test in the WWF and he proved he could be a convincing heel and work with anyone.
WWF WrestleMania VII — March 24, 1991
He already proved he could work with big men but this match showed why he could work well with smaller opponents as well. They’d already worked together in the lead up to WrestleMania a number of times, including on The Main Event and on live event loops. The Boss Man came close to winning the Intercontinental Championship here, but still shined despite picking up the win via disqualification.
As it turns out, they worked well together as partners or foes, with the two teaming up later on in both men’s final WWE runs, including pairing up for Boss Man’s final tag team match in WWE against the Hardy Boyz in 2002.
WWF SummerSlam — August 26, 1991
This matched showed how good Traylor could be as a babyface and gave us a fun stipulation—the loser would be booked in a New York City jail for 24 hours. The match worked so well because of the two men in the match, Boss Man and The Mountie, the latter of which was a riot as he thrashed about while being booked for lock-up.
WWF Survivor Series — November 25, 1992
Nailz is more infamous now for being fired from WWF, but his feud with the Big Boss Man is memorable for other reasons. In 1992, Nailz debuted as an ex-convict who alleged that the Boss Man had attacked him while he was incarcerated for crimes he didn’t commit. Nailz handcuffed and attacked him with a nightstick and went on a winning streak until they finally met in a Nightstick Match at Survivor Series. The matchup was unique for the time, both for the gimmick itself and because it saw the prisoner go against the inmate. Boss Man was the clear babyface by this point, but it also helped propel Nailz to other feuds with The Undertaker and Ultimate Warrior, and solidified Boss Man as a top WWE star.
WWF Raw Is War — November 30, 1998
The Big Boss Man is synonymous with the WWF Hardcore title, with many of the best moments and matches of his second run with the company being related to a fight for the title.
The Boss Man returned from WCW in October 1998 wearing black SWAT gear, and he quickly won the Hardcore Title from Mankind in an underrated ladder match on RAW. The match was short and full of shenanigans (including a well-timed run-in) but both men played to their strengths and made it a memorable encounter.
WWF Summerslam — August 22, 1999
A month before their ill-fated Kennel From Hell match, Al Snow and the Boss Man clashed at SummerSlam 1999 in a brawl that spilled into the streets and a local bar. This one was before the “24/7” gimmick and comedic elements came into play, but it was still brutal and fun. Two of Boss Man’s most infamous moments came at the expense of Big Show and Al Snow, but it’s hard to argue that his feud with Snow provided some memorable brawls.
Now, more than ever, it’s time
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