According to The Big Show, The Baby New Year segment was his all-time worst.
"There [has] been a lot of stuff I've done has been absolutely horrendous. But I think for me personally, the worst thing I've done was when Vince [McMahon] made me do the 'Baby New Year' thing because it was so freakin' awkward. He had me in a freakin' diaper with a New Year hat and he wanted me dancing and all I could think of, it was like some billionaire masturbating video where he [has] got some fat guy. You can imagine Vince in some dark room looking at it on a big screen, like, 'yeah, now s--t in the diaper, you fat bastard! s--t in the diaper! That's it!' It was just so uncomfortable."
The Big Show speculated that WWE Chairman Vince McMahon had Show in that ridiculous getup to embarrass and consequently motivate 'The Big Nasty Bastard' to lose weight.
"I got fat, so he goes, 'so you're a fat New Year Baby. Maybe you should lose some weight.' But that's the kind of relationship I've had with him, 'he's getting fat - I need to motivate him. Let me embarrass him.' Do you know what I mean? The diaper worked." The Big Show added, "that insane, crazy Vincent Kennedy McMahon actually does know more than I do. He's actually a smart guy. Believe it or not, he's a brilliant individual. That's funny. That literally was the most awkward thing I've done."
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Source: Talk Is Jericho