The guy who killed bruce wayne’s parents if im not mistaken

good story, liked the twist that the assassin's is the the "the man responsible for the legend" per say

but i wonder

will his noble fantasm turn Illya on a hero herself or no?

also I got a suggestion

why not put Sans as a servant? he could be the lazy caster of the grail war

Well if it ain't Joe Chill

Meh...
Not make any sense to not apply EU(or LEGENDS!) to Han Solo...
Do you actually know - in Nasuverse, Legends or simple jokes from people, have a really effect on servant abilities and powers.
Like you know - Corellian Empire. And the Han Solo is the only living and legal heir of Empire-Han Emperor-and must have "Imperial Privilege"...

Or, or WHATS about a Dathomir. Han win a OWN a WHOLE PLANET in card game.
Like you know Grey, a girl who was a temporary owner of just a sphear what fastens the planet together. And gets skill from that to her Servant.

How powerful the skill will be - if it's supposed to reflect planet ownership... And of cource in FATE a PLANETS has a large amount of skill and powers.

Just as he is the monarch of the Alderaan people because of his marriage to Leia. Just like he is the husband of the president of the galactic republic.

I won't even talk about the lack of Charisma in skills(coz he lead armies and fleets into many battles), Strategy (coz he directed campaigns and operations), skills in robery, stealth, fake identify...

Seriously, it doesn't make sense...

For a second, I thought this was going to be Vash. Figured he would be perfect since you did Wolfwood earlier. He uses guns and has a no-kill rule and is feared by everyone except Milly, Wildwood and Meryl.

Really wish we got more of the James Bond one !

Can I make a few suggestions? I have a list of a ideas for Servants.

Here is my suggestion for Berserker. Make it Broly from Dragon Ball Super. Maybe Illya summons him and she gets what she needs.

My Suggestion for Caster is, Nine The Phantom from BlazBlue. You could have either Shirou find her after she wacks her previous master and Shirou gets with a Hot older Woman, or instead Rin Summons her to be her Servant with Nine being Rin's new Teacher.

For Saber, Maybe Shirou summons Betsy Braddock/Aka Captain Britain/Pysloke. Make Psylock have all the powers that she had in Kwannon's Body as well as her original form, and also the powers she has as Captain Britain. Also maybe Shirou also scores with her and it gets Rin and Sakura Jealous as she is a hot older Woman? And seeing as Betsy Braddock is Bisexual maybe Shirou gets a harem of women as along as Betsy has some fun with Shirou and the girls as well? Just a Thought.

For Assassin, maybe Ahri from League of Legends appears. She could be a Caster and Assassin combo like Semiramis. That would be cool.

For Avenger, Maybe you can have the Ghost of the Uchiha. Madara Uchiha appear. That would be awesome!

For Archer, maybe you can have Mercedes from Odin Sphere Lethrasir arrive. Maybe she appears in the Fourth Holy Grail War.

For Rider, maybe you can bring in Samus Aran as she can also serve as a Archer as well. Again Shirou could get with an Older Woman.

For Foreigner(its an actual class)for a Holy Grail War, Make it Ben 10.

For Lancer, Make it Sun Wukong. Yes, The Monkey King from Journey to The West. Read the Novel for Sun Wukong's feats and powers and also Look at Death Battle!'s Sun Wukong vs Hercules video as it is awesome!

For Ruler, Maybe Naruto Uzumaki?

Do Dante from Devil May Cry next.

This is the guy who killed Batman’s parents Joe Chill

Please do Cosmic Garou

the Assassin that started the world's greatest Heroic Detective

I need to see Robert say 'Discombobulate'

Hmmm... Haven't updated for over three years but whatever, Simon from Gurren Lagan, because why not?

Yes, you can put all the forms of Gurren lagann in, even Super Tengen Toppa, but I'm going to suggest using up to Arc-Gurren Lagann

Joe Chill, depending on the canon. The man who made the Bat. And poor Ilya, but at least in this timeline she gets to be a superhero. If she lives.
Oh, and the idea of summoning someone who is unremarkable except for 1 action which changed the world, on accident is fascinating.

One important thing about Cain is, while his reasons for saving the day are overinflated, he is actually that good. Or at least, better than almost any other man. Dude kept up with and impressed a space marine with his sword play, He's a coward and luckier than any other man, but he's also a master combatant when forced to fight.