I have two. Both of them end in his defeat, but it gave me a different perspective on the character.
The fist was when he finally gets to Mephisto's realm and finally makes that bargain he's wanted do do since he was a kid: Get his mom back. He sacrifices Dr. Stranges soul in exchange for hers. Mephisto agrees and then when she's freed, Doom's glad to finally see her again. Then she's told that he sacrificed an innocent soul just to save hers and she disproves. So much so that she actually gets angry at him and refuses to go anywhere. Poor Doom.
The second was the final scene in Waid's "Unthinkable" FF arc. Spoilers for anyone who hasn't read it (and shame on you if you didn't because his run on the FF is the best one ever) but right before Doom is sent to Hell, the last person he talks to is Reed Richards, the dude he blames for pretty much ruining his face. Doom fakes this whole speech about if Richards lets him fall into Hell, he's no more of a hero than Doom is. Reed doesn't buy it because a) he's smart and b) this entire arc was Doom making Franklin and Valeria's life a living hell (quite literally for poor Franklin). So Reed basically tells him to screw himself. Right before Doom falls through the portal, he's all like "Fine, but if I'm going to hell, I'm leaving you the same pain you left on me" and disfigures Reed's face. Really goes to show you that Doom will go to extreme lengths if you wrong him just once.
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