1. Regrettable Ink
By far the most embarrassing thing Undertaker has been involved with was not part of an angle, segment, or match. This was all too much real life. Having his wife Sara become involved in angles was a bad enough decision but the worst decision of all came when The American Bad Ass got some new ink---SARA in big letters prominently burned into his neck. This was a sweet enough gesture in the name of love but it was completely counter to the essense of the Undertaker character, whether the Phenom or the American Bad Ass. He might as well have gotten MOM inside of a cartoon heart. As you might expect, getting a woman's name tattooed on your body is just testing fate. Even though the couple had two children over the next few years the marriage just didn't last and the two ended up divorced. Sara might have left the ranch but her name stayed on the neck. At least for awhile. Although looking in the mirror Taker would see the letters reversed, any new female friend couldn't help but stare at the name of his ex-wife and mother of his children. Case in point: around the same time as Taker was being linked to WWE Diva Michelle McCool the SARA tattoo began to fade and has since been completely covered up. In any event, the whole ordeal was awkward as hell and more embarrassing than anything Vince McMahon could have come up with. Inferno matches? Almost always losing his signature Buried Alive matches? Getting pinned by Khali? What are some of your favorite awkward Undertaker moments?