The first crowning moment of awesome is undoubtedly the PC single handedly assaulting a Sabbat warehouse and proceeding to blow it up. The fact it was obviously a suicide mission LaCroix intended to use to dispose of the PC only makes their next encounter all the sweeter.
The confrontation between Gimble and the PC is its own moment of awesome. A human serial killer encounters the ultimate predator.
The player character slaughtering their way through Chinatown when they finally put down Ming Xiao once and for all. The fact that you finally get payback for the way she's treated her this entire game is extremely enjoyable.
The player character on his Matrix-esque assault through LaCroix's forces up until the final confrontation when you kill his Sheriff is just one long moment of awesome. It's one of the few games that imitate a player's typical reckless but awesome in-game planning.
Admit it, the Malkavian PC name dropping the Yama Kings and the Demon Emperor of the Sixth Age to Ming Xiao as a Take That to her "Cainite superstition" mocking is just awesome.
A subtle one occurs when the PC finally confronts LaCroix for the last time and he tries to Dominate you into doing his bidding. Up until this point, the PCs have been helpless but to do as the Prince commands. Having killed their way through half of Los Angeles' supernaturals, the PC just shrugs off LaCroix's final command. This leads to LaCroix's Villainous Breakdown.
Various theories abound to why the PC is able to do so. This include the PC's Generation going down, them raising their willpower off-screen, and other more esoteric explanations.
All of the endings are awesome in their own way except the LaCroix and Kuei-jin endings. However, the Independent deserves special mention. Having been used as a pawn by everyone in Kindred society, the player character simply flips off the Anarchs when they try and recruit him. It's the best if you're Ventrue. You're from the line of aristocrats, and you reject Lacroix, the Camarilla in addition to the Anarchs.
During the werewolf chase scene, the player can lure the werewolf onto the observatory and kill it by crushing it to death with the doors. After the Lupine had been hyped up as pretty much invincible, it is really satisfying to do (and you can get extra experience from doing so as well).
Not to mention the amount of XP you get is the highest you get in the game from a single act. It is as if the game itself acknowledges the awesomeness of your feat.
The game is a Gambit Roulette by the last person you'd expect. Jack is behind a multiple stage plot to overthrow the Prince. Setting up a fake sarcophagus with C4, Jack manipulated both the Kueijin and LaCroix factions into wiping each other out. It's so impressive that Cain himself decides to help him out. Pretty amazing for a guy who looks like a drugged out Hell's Angel.
The fact he has a front row seat to watching the show with the Ankaran sarcophagus' resident only helps the awesome.
When the player is attacked by the Sabbat during the tutorial, Jack shows that There Is No Kill Like Overkill by killing off the two Sabbat vampires. How does he get rid of the first one? He slashes the vampire's neck, stabs him in the back, and breaks the vampire's spine over his knees, right before activating his Potence discipline and sending the second Sabbat flying.
Gets two in the game. The first one is when he rescues your PC after they are ambushed by the Sabbat and beaten up. Nines manages to intimidate three Sabbat not by his sheer badassery but by pointing out he has a grenade in his pocket. When one of them calls him on it, he one-shots him over his shoulder. The second Crowning Moment of Awesome is when he apparently rips a Lupine's head clean off.
He keeps the Lupine's head on his bed.
There's a reason the Malkavian PC calls Lacroix the "Jester-Prince" and Strauss the "Wizard-King". The Camarilla ending shows why.
The Taxi Driver
The revelation of his true identity as Caine, The Father of All Vampires. It says a lot about the character that this is the profession he's chosen.
If you're a Malkavian character, there's a good chance that upon realising this your character flips out and is reduced to screams and whimpers of "Oh god oh god oh god oh god!". Caine lets you get it out of your system before continuing.
E gets one if you blackmail Lily. Horrified by the things her frenzy drove her to do, she begs you not to tell E, certain that she'll lose him for good if he finds out. She can't pay you but will do anything if you keep it a secret. When you can't get anything useful from her you have an option to tell E everything. His response is to suggest that you shove it. One of the weakest characters in the game and he gets to look down on you.
Gary Golden:(unseen, while the PC is trying to make him show his face) You're used to getting what you want, aren't you, handsome. People just love your charisma, your face. They eat your words up like the rats eat the cheese in the trap. Oh, boss, where do you think you are? (...) Gary Golden:(after revealing himself) Boo! Player Character: You are the most offensive and obscene thing I've ever seen. Gary Golden: En garde, Toreador. You vainglorious, narcissistic poseur! How I loathe that determination of your kind to belie your true nature with Paris fashions and pomp. You are a dead thing - a creature of the shadows. Start acting like one.
Heck, Gary gets under the skin of a Malkavian, mocking them and saying maybe he's just another of the voices in their head. It's the only time a Malk will be so annoyed, they'll talk normally, with a "Where. Are. You?"
Ordinary Humans or Ghouls
Believe it or not, Stanley Gimble, whom you speak to in the first bounty hunter sidequest while looking for Carson, has one in his backstory. You learn that rather than just modeling, he also provides prosthetic limbs. No, that's not the awesome part. The awesome part is that he's so dedicated to his work that when he realized that his prosthetic limbs were sub-par, he decided that his work would only improve if he knew what it was like to have to use one...so he deliberately cut off his own arm and replaced it with a prosthetic, just to improve his work! Of course the awesome is mitigated slightly by the fact that he's also a horrible serial killer who lures people to his lair to slice them up for limbs.
You wouldn't expect it from Knox Harrington of all people, but Knox can pull a fast one on the player if the player doesn't have a high enough Inspection statistic. You know that story Knox gives you about the Asian dude who keeps stalking him and freaking him out, which is what eventually leads you to kill an Asian vampire in the Foxy Boxes store? That's actually a lie. The Asian dude wasn't stalking Knox; Bertram Tung asked Knox to plant you that story to trick you into removing a spy that was getting in Bertram Tung's way. So if you don't figure that out, you've just been tricked by an idiot! Surely a moment of awesome on Knox's part; not so much for the player.
This is a mostly off-screen example, but Romero's been fighting off zombies for most of his "ghoul-hood", before you ever show up. That's no small feat for someone who isn't as powerful as a vampire.note Though he may just be a Defender (a la Hunter: The Reckoning), so he's more of a Badass Abnormal.)
Another off-screen example, but if you get the Astrolite by reasoning with the head thug using persuasion, seduction, Domination, or Dementation, rather than killing all the thugs as Mercurio wanted you to, then Mercurio eventually tells you that he killed them all himself to get the payback he wanted.
The development team gets a big crowning moment of awesome for creating the game. Not just because it's one of the best role-playing games of all time but the fact that it also manages to make atmospheric the 2nd Edition world of Vampire: The Masquerade. By that point, the sheer amount of silliness had seriously watered down the horror vibe of the game. However, everything was included in the game and didn't remotely detract from the horror.
For example Kindred of the East in all their other dimensional glory, a member of the Nagaraja sect from Dirty Secrets of the Black Hand, and even a fucking wereshark!
After the company got shut down, a number of developers stayed on to make the official patch. Just because they didn't want the game to have all the many glitches it had on launch. Talk about Doing It for the Art.