* BadassDecay[=/=]DorkAge: His time in WCW, also his 2003 WWE run on ''[=SmackDown!=]''.
* CrazyAwesome: Essentially his character whenever he was a {{face}}.
* [[SugarWiki/FunnyMoments Crowning Moment of Funny]]: After the famous incident during ''Wrestling/{{SummerSlam}} 1989'' where he mooned Wrestling/RickRude, Piper asked Gene Okerlund during an interview "What's a Scotsman wear under his kilt?" [[spoiler: "His shoes!"]]
* [[SugarWiki/HeartwarmingMoments Crowning Moment Of Heartwarming]]: His famous ''Wrestling/{{WrestleMania}} VIII'' match with Wrestling/BretHart, where, after teasing a heel turn (and wielding a ring bell at that!) he just couldn't bring himself to screw over his old friend. Bret ultimately wins, but the two embrace afterward in a ''very'' rare show of respect from Piper.
** Piper was voted to be Wrestling/RicFlair's partner at ''Cyber Sunday 2006,'' but had to be withdrawn from storylines shortly afterward when it was discovered that he had cancer. Piper made a full recovery and credits the fans' vote as being what saved his life.
* DudeNotFunny: His, let's say, unusual choice of attire for his ''Wrestling/{{WrestleMania}} VI'' match [[http://www.youtube.com/watch?v=E5RXJ0vgQxs with Bad News Brown.]] UnfortunateImplications ahoy.
** Not helped by Wrestling/AndreTheGiant allegedly deciding to switch out the solution to get that stuff off Piper with water after the match.