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Mamoru Chiba/Tuxedo Mask

Drop Point: DayBreak Town
  Mamoru Chiba is Tuxedo Mask, destined lover of Sailor Moon/Usagi Tsukino/Princess Serenity and Prince Endymion, prince of Earth from the past.   He's the "I only aid Sailor Moon at the last second while giving commentary and vanish after my 5 seconds of screen time" in the 90s anime which has become a meme at this point and his role in that period is laughable, heartbreaking, and annoying.   From finding out Usagi is Princess Serenity reincarnated, he had an adverse relationship with the main character. They eventually are able to fall in love with the his precious "Odango". However, his character goes in different directions depending on which version of the medium.   In the 90s anime, he has amenisa and is looking for the Silver Crystal while aiding Sailor Moon, going by his "Lupin" monikar. His only attack is using a rose to distract an enemy about to kill Sailor Moon and give her time to use her attack. Mamoru eventually gets captured by the Dark Kingdom and becomes a pawn of Queen Beryl for half of the series and breaks free in the last episode of the first season.   Season 2, he has amenisa again and doesn't remember Usagi for a time until the end of the Doom Tree arc while in the second half of the series breaks up with her due to having nightmares of a dark future where she dies if they were to wed. He breaks her heart and it takes sometime before they reuinte and find out the reason why.

There is a lot more but I (J who is writing this) is taken too long so watch the series.
Also as a sidebar, his attire in the 90s is atrocious and it doesn't do him any favors.
In the manga and Crystal version, he is intelligent, offers more assistance, and is a damn great romantic partner for Usagi, and a suave dude that is on par with Kurama from YYH, he is a better character all around.   He throws roses as a patent attack in the 90s that doesn't really do anything and is a decent combatant with his cane however in later media he gains access to a Kamehameha-like attack, called "La Smoking Bomber",which he uses primarily and a good sword fighter when he is in his Endymion form (he's a knight). He also gains his Golden Crystal, his power source, and second only to the Silver Crystal (in J's words) though it's unknown of its capabilities so it could rival said crystal.   Through it all, Mamoru will always stand with Usagi and they will usher in a golden age for earth in their reality.   Lore: Mamoru will mostly help the Sailors and civilians. He will continue his studies in science and gain friendships with some of the cast in this world.
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