Those boss fights that inspired memories both good and bad.
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M. Bison: A fighting game nightmare. In all seriousness though, whether I like it or not, Bison is undoubtedly memorable and iconic to the fighting industry.
In Dynasty Warriors (DW5 in particular for me personally) Lu Bu is a nearly invincible monster at the Battle of Si Shui Gate. While I have killed him several times, his classic, over-the-top introduction and later displays of ridiculous power will not soon be forgotten.
I was stumped when my brother and I first killed Dagoth Ur. He was a complete push-over! Little did we realize that this was only his first form. His second form in the chamber with the Heart of Lorkhan is invulnerable and does massive damage. This leaves you to avoid him and strike at the heart, and all the while he taunts you. Then you destroy the heart and maybe exclaim something like: "Screw you Dagoth Ur! Eat it!" This is a sign of a truly memorable fight.
The fight (actually five fights) against Ansem at the end of Kingdom Hearts makes him particularly memorable. His shouts of "Turn to DARKNESS!" "Come Guardian!" and "Submit!" have affixed this guy in my mind as one of the most memorable boss fights I've ever encountered.
Every time I fought him counts. While I hate him, this guy is one of those that falls under the "bad memories" category. Relentless cuss! When will you truly die?! Plan on a comeback in the next Final Fantasy?!
Riku's boss fight (before he is possessed by Ansem) is actually fairly memorable on it's own. He fights Sora using the power of darkness, and loses (because light trounces darkness). The battle later on with Riku-Ansem (Ansem controlling Riku) is highly memorable, and pretty dang difficult. "Behold the power of darkness!"
Nightmare's battle sequence with Siegfried in Soul Calibur III is what, more than anything else, makes him so iconic for me. He is a great villain.
The entire sequence with Hircine in Bloodmoon makes him an incredibly memorable boss. The quest "Hircine's Hunt" is where most of this comes from as he pits you against other prisoners (including a giant) and his "hounds" which are werewolves. Once you reach him, you choose an "aspect" of him to face. Strength, Speed, or Guile. Each yields a different reward. He leaves you with his glacier crumbling, and his resonating laugh echoing in the air.
This version of Jun controlled by an evil spirit is most memorable indeed. Very tough boss! I hope they make this canon now that Jun is coming back. EDIT: I originally had Unknown listed here, but it looks as though Namco has finally decided to follow through on their idea. Yes!
The surprise boss of Gauntlet: Dark Legacy. Once you've finally killed Skorne, twice, the players leave in victory. Then, suddenly - Garm! He unexpectedly absorbs the dead demon's powers and becomes an uber super-boss.