It's no surprise that Shawn Michaels is the number one choice as the biggest "boytoy" in WWE history. Just look at his famous song lyrics.
I think I'm cute. I know I'm sexy. I've got the looks that drive the girls wild. I've got the moves, that really move 'em. I send chills up and down their spines. I'm just a sexy boy, sexy boy. I'm not your boy toy, boy toy. I'm just a sexy boy, sexy boy. I'm not your boy toy, boy toy.
It's one of the most iconic theme songs in the history of WWE. At first it was sung by Sensational Sherri, who managed Shawn when he first turned heel on his partner Marty Jannetty in 1992. It was a great pairing with Sherri out there holding a mirror while Shawn danced around the ring admiring himself. He was never really nice to her and kicked her to the curb when he didn't need her anymore, which only added to his heel heat. Michaels used that brash attitude and willingness to push the envelope to make a huge name for himself in the mid-1990s. He bragged about how he could "go all night" in reference to long matches, but also his reputation with the ladies. A babyface run soon followed from 1995 to early 1997, so they toned down the aggressiveness of the character. When he became more of an aggressive heel with Degeneration X in 1997 it really upset people like Bret Hart because he would do things like hump the Canadian flag, which was very disrespectful and pushed the limits on what it meant to be a heel. In a lot of ways, Michaels was the Attitude Era before anybody else, but sadly a back injury forced him out of action in 1998 when that period really took off. By the time Shawn returned to the ring in 2002 he was a changed man. He was married and he was a father, so he wasn't like the guy that was danced around the ring a decade earlier. However, the song remained and the nickname is still with him even today as a nearly 50 year old man. He's always going to be known as "The Heartbreak Kid" for the rest of his career even though he looks like nothing like a "kid" anymore. Michaels is arguably the best in-ring performer in WWE history as well as the definition of what it means to be a "boytoy" in wrestling. He took it to another level that will probably never be topped.
John wrote at WhatCulture from December 2013 to December 2015. It was fun, but it's over for now. Follow him on Twitter @johnreport. You can also send an email to mrjohncanton@gmail.com with any questions or comments as well.
