Prepare for the spookiest, hell-raising and terrifying night of the year with our picks for the 20 best spooky wrestling gimmicks. Here we go from 10 to 1 in this second part of our look back and beyond at these scary and terrifying characters, just in time for Halloween. (evil laugh)
Dark Allie, Darby Allin, Thunder Rosa, Waylon Mercy, Lucha Underground (Matanza/Jeff Cobb, The Moth Tribe, The Black Lotus Triad) and The Great Kabuki.
10. Jake Roberts
Jake Roberts started his career in the Louisiana area in 1974 and worked as a referee and wrestler competing in Mid-South Wrestling, Mid-Atlantic Championship Wrestling, and Georgia Championship Wrestling. Being a good wrestler in the late 1970s wasn’t enough and he would travel up to Canada to work in Stampede Wrestling in order to help develop a character. In 1983, while in Georgia Championship Wrestling, Roberts would join up with Paul Ellering and his stable the Legion of Doom.
Upon his debut in the WWE in March 1986, Roberts would start carrying around a snake around in a canvas bag and would defeat George Wells at WrestleMania II, using his snake, Damien, to his advantage, wrapping it around his head. His evil side would be shown again during his feud with Ricky “The Dragon” Steamboat where he would DDT him onto the concrete floor right in front of his wife, rendering him unconscious. It was in this feud that we would see a specialist match called a Snake Pit Match (a no-DQ match).
Jake Roberts’s microphone skills are one of his strongest tools and because of this was given his own talk show segment called “The Snake Pit” in late 1986, this segment would continue till July 1987. Around the time of the first Snake Pit segment, Roberts began becoming very popular with the fans even while being presented as a villainous character. This can be seen during his program with Randy Savage in November 1986 and the crowd reaction to him hitting a DDT on Hulk Hogan during his talk show segment, the crowd began chanting for him and the DDT this ultimately caused the potential program between the two to be scrapped. In 1987 Roberts would turn face and entre a feud with The Honky Tonk Man after Roberts was hit with a guitar that resulted in his neck being injured, they would end up facing each other at WrestleMania III, with Alice Cooper being in the corner of Roberts.
By April 1988 he would enter a feud with Ravishing Rick Rude which would centre around Rude wanting a piece of Jake Roberts real-life wife, Cheryl and in March of 1989 he would have a program with André the Giant focusing on André’s fear of snakes and would face him at WrestleMania V. He would go on to feud with Ted DiBiase throughout the end of 1989 into 1990 cumulating in a match at WrestleMania VI and at WrestleMania VII Roberts would face Rick “The Model” Martel in a Blindfold match, after Martel blinded Roberts with his cologne names “Arrogance” in early 1991.
His most famous and harrowing performances and feuds would be with the Ultimate Warrior in the summer of 1991. The Warrior had come to Roberts to help him defeat the Undertaker, Roberts explained he would need to pass three tests in order to gain the “knowledge of the dark side”, the third task was for Warrior to walk through a room full of live snakes to reach a chest containing “the answer”, upon opening the chest he would be bitten by a King Cobra, as he became weakened by the bite it would be revealed that Jake Roberts had been working with The Undertaker and Paul Bearer all along. He would later remark that you can “Never trust a snake”, turning Roberts Heel for the first time since 1987. His vignettes and promos at this time enhanced the character immensely, making him a more sadistic character on screen, unfortunately with the firing of the Ultimate Warrior the night of SummerSlam, the program was cancelled, but Roberts would continue to show dark and menacing tendencies when he faced off against Randy Savage post-SummerSlam. His first act of villainy would be to ruin the post SummerSlam reception of Randy Savage and Miss Elizabeth; she would open a box containing a live cobra and see her husband attacked by both Roberts and The Undertaker. The feud would run until Saturday Night’s Main Event XXX, afterwards, he would feud with The Undertaker up until WrestleMania VIII, where he would leave the company shortly after.
Jake Roberts would leave the WWF and head to WCW to work in 1992; he would leave that very same year and spend 1993 and 1994 touring the independent circuit. Roberts would return to the WWF between 1996 -1997, performing in ECW 1997 – 1998, and return to the independent circuit in 1999. He would work for TNA in 2006 and 2008 and return to the WWF/WWE in 2005, where he would work with Randy Orton during his “legend killer” gimmick and in 2014 to attack Dean Ambrose (Jon Moxley), he would be inducted into the WWE Hall of Fame by Diamond Dallas Page on 5th April 2014.
Jake Roberts to this day still gives off a menacing presence on screen; he is currently signed to AEW where he works as a manager for Lance Archer. His first appearance with the company was as the blackjack dealer for the Women’s Casino Battle Royale referencing his infamous “You wanna play 21?” promo from 1999.