Old Shame: His Wrestlemania X7 heel turn. He admitted it wasn't a good idea to do the turn in his home state (as he'd be cheered no matter what), and that what henote his character in kayfabe that is should have done is stunnered McMahon right then and there after handing him a beer.
Perhaps inevitably, Austin isn't proud of his domestic violence history.
"The Ringmaster" was a character that was only created in order to distance Austin from his past in other promotions (particularly his "Stunning" phase in WCW where he won their United States Championship). The character was flavorless and it just buried Austin's early going in WWF, which is a dark spot on what would eventually become the "Stone Cold" phenomenon.
During a Raw segment with CM Punk he admits that he finds the WHAT? catchphrase annoying.
Romance on the Set: Debra Marshall divorced her then-husband Mongo McMichaels and emigrated to WWF along with Steve. This is foreshadowed, nicely, in a Nitro storyline where Ric Flair woos away Debra and adds her to his ever-growing list of conquests, causing Mongo to go berserk in the announcer's booth.
Brandon Stroud: All because Ric Flair wanted a different color of mid-30s wrestling wife tail.
Short-Lived Big Impact: Was only on top for one or two years but the general consensus is that small time frame is bigger than anyone else's biggest one or two years on top.
Throw It In: Austin's "Stone Cold" moniker was inspired by a comment from his wife at the time; she handed him a cup of tea, and remarked that he should hurry up and drink it before it got "stone cold".
Mick Foley mentioned in his book how, at the time, Austin was searching for a suitable "cold" nickname to suit his character— and was very lucky for that one to come along, as the writers had been coming up with some stinkers. Foley mentioned Austin could have had the exact same personality, but the moment he was announced as "Chilly McFreeze", there wouldn't have been much hope.
Austin actually appeared on at least one TV broadcast as "Ice Dagger" Steve Austin. Which... isn't that bad of a nickname, really.
The WHAT? catchprase. He was calling Christian one afternoon and left a voicemail. He said "what?" every other line for some reason. Christian found it so funny (if incoherent) that he suggested that Stone Cold use it. The rest, they say, is history.
What Could Have Been: Austin and Pillman, former tag partners with a great relationship and great chemistry, could have had some legendary feuds over the years had Pillman not died at 35.
Austin was also supposed to feud with Mick Foley, with Foley being revealed as the "Higher Power". Foley declined, as Foley's numerous injuries had caught up with him at this point.
Austin was supposed to wrestle Hogan at Wrestlemania 18 instead of the Rock. Austin actually declined, believing that his style and Hogan's wouldn't mesh, and that the match wouldn't live up to the hype.
Paul Heyman noted on The Rise And Fall Of ECW DVD that he wanted Austin as ECW champion. Austin declined, noting that being so close to making it made him want it even more, in character, adding to "The Extreme Superstar" persona.