From one Londoner to another... one of the most famous serial killers the world over in that he was never caught. I'm speaking, of course, of Jack the Ripper. Who was he? Or was he even a he? Scholars debate these very questions and more 'til this very night and, while many theories have been proposed over the years since the grisly murders, the killer was never caught and enough time has passed that we will very likely never get a real answer.
So, naturally, I'm going to build him in D&D!
In the interest of spoilers, I will be using the version of Jack from the Alan Moore graphic novel and the later 2001 film From Hell, where Jack was definitely Sir William Gull, in real life the physician ordinary to Queen Victoria herself. In the movie, he was played masterfully by Ian Holm, making it the man's third scariest role after Ash from Alien and heroin addicted Bilbo from The Lord of the Rings: The Fellowship of the Ring.
...yeah, no, I'm not putting the picture or gif here, that's officially in 2 spoopy 4 me territory.
As always, we'll be using the Standard Point Array from the Player's Handbook - no, I'm not implementing anything from One DND at the present and I don't see myself doing so any time soon. These builds are and will remain with 5e.
Intelligence: 15
Sir Gull is a physician, after all. With that comes a great deal of studying from books over the years.
Wisdom: 14
However, Medicine is a Wisdom-based skill. This represents his experience in practical medicine, not just the theoretical.
Dexterity: 13
Gull had to be swift to commit those murders not only quickly, but without getting caught.
Constitution: 12
It's a little lower than I would like, we just need other things more for this build.
Charisma: 10
Give him credit, he was played by Ian Holm.
Strength: 8
No doubt he'd need more than a little strength to do the deed in real life, this is just again a case of us needing other things more.
Jack is a human, specifically a Variant Human, which will get us a free Skill and a Feat of our choice. For the skill, we're going to go with Medicine to best reflect his medical training. For the feat, we're going to go with Prodigy from Xanathar's Guide to Everything. Prodigy nets you another skill, a tool proficiency, and fluency in a language of your choice as well as Expertise in one skill of your choice, in this case we'll be bumping up Medicine to allow you to double your proficiency bonus for that skill.
As for the free skill, we'll be taking Stealth.
Also, for being a Variant Human, Jack gains a +1 to two different ability scores. In this case, we're beefing up Dexterity and Intelligence.
For background, we'll be taking Guild Artisan, as Sir Gull did hold connections to the Freemasons within the fiction of From Hell. With the background, we get skill proficiency in Insight and Persuasion as well as one free set of artisan's tools and yet another language of your choice, giving Jack the Ripper a grand total of four languages and four separate skills (and expertise in one!) before he has even taken his first level.
And our first level is going to be... Rogue (1). Why Rogue and not something more medically inclined? Simple! If you start as a Rogue, you get all the benefits of being a Rogue - particularly four skills right off the bat for a grand total of eight. Thus, from first-level Rogue, we're going to take Deception, Intimidation, Perception, and Sleight of Hand. Rogues at first level also gain a Sneak Attack at a 1d6, proficiency in all simple weapons, hand crossbows, longswords, rapiers, and shortswords, light armor, and thieves' tools. They also gain two skill proficiencies that they can once more gain Expertise in, we're going to go with Stealth and Sleight of Hand, doubling your proficiency bonus when either of them is used.
Also, first level Rogues learn Thieves' Cant, which makes for five languages now. Jack also has proficiency in Dexterity and Intelligence saving throws.
Moving to second level, Rogue (2) gains a Cunning Action, meaning that Jack can take a bonus action on each turn in combat so long as that action is used to Dash, Disengage, or Hide.
Third level Rogue (3) must pick a Roguish Archetype. In keeping with our theme, Jack is going to become an Assassin. Assassins gain proficiency with the disguise kit and the poisoner's kit. They also gain the ability to Assassinate, giving them advantage on attack rolls against any creature that hasn't yet taken a turn in combat and in addition allows any attack Jack makes against a surprised opponent to be a critical hit. Neat!
Oh, and his Sneak Attack gets bumped up to a 2d6.
Fourth level Rogue (4) sees Jack earn his first Ability Score Improvement or Feat. The Healer feat will allow Jack to use a healer's kit to stabilize a dying creature and make it regain 1 hit point. He can also use a healer's kit to restore 1d6+4 hit points to a target, additional hit points equal to the creature's maximum Hit Dice can also be added. Of course, this ability can only be used once on a creature per long rest.
Fifth level Rogue (5) sees the Sneak Attack bump up to a 3d6 as well as giving Jack the ability of Uncanny Dodge, meaning that he can halve the damage of an attack he is hit by coming from someone he can see.
Sixth level Rogue (6) gains Expertise in two more skills. Deception and Intimidation seem like very good ideas indeed!
Seventh level Rogue (7) gets the Sneak Attack bumped up to 4d6 and gains Evasion. Now, when rolling a saving throw from an attack, Jack now takes no damage on a successful save and half damage on a failed one. Pretty neat!
Eighth level Rogue (8) means another Ability Score Improvement or a Feat. Let's keep up with the boosting Intelligence and Dexterity.
Ninth level Rogue (9) sees an Assassin gain Infiltration Expertise, basically allowing Jack to create a false identity for himself at the cost of 25gp and a week's worth of work. When he adopts the persona, others believe him to be that person until they have a very good reason to think otherwise.
Sneak attack is also at a 5d6.
Tenth level Rogue (10) sees Jack get another Ability Score Improvement or Feat. Skulker gives Jack the ability to try to hide when lightly obscured from a creature that he's hiding from, makes sure that he doesn't reveal his location when he misses with a ranged attack against an opponent, and dim light no longer imposes disadvantage on Perception checks relying on sight.
Eleventh level Rogue (11) bumps the Sneak Attack to a 6d6 and gives Jack the power of Reliable Talent, meaning that any ability check that allows him to add his Proficiency bonus cannot be any lower than 10.
Twelfth level Rogue (12) gets yet another Ability Score Improvement or Feat. Keep pumping up your Intelligence and Dexterity.
Thirteenth level Rogue (13) gets a Sneak Attack boost to 7d6 and Assassins gain the ability of Impostor, which builds on the earlier Infilitration Expertise quite a bit. Jack can now perfectly mimic another person in their speech, writing, and behavior after spending at least three hours studying all those components. He also gains advantage on any Deception check against people who are beginning to notice something is amiss and may see through his ruse.
Fourteenth level Rogue (14) gets Blindsense, meaning that he is aware of any hidden or invisible creature within 10 feet of him.
At fifteenth level, the Rogue (15) has developed a Slippery Mind. Congratulations! You now have proficiency in Wisdom checks, one of the most called for saving throws in the game! Also, the Sneak Attack is at a 8d6.
At sixteenth level Rogue (16) gains another Ability Score Improvement or Feat. Go for Slasher from Tasha's Cauldron of Everything. Bump up your Strength or Dexterity (in this case, Dexterity) by 1 to a maximum of 20. When Jack hits a creature with slashing damage, he can reduce their speed by 10 until the start ofh is next turn. When he scores a critical hit that deals slashing damage, he imposes disadvantage on all their attack rolls until the start of his next turn.
At seventeenth level, Jack as a Rogue (17) in the Assassin Archetype gains the Death Strike. When he hits a surprised creature, they must make a Constitution saving throw (DC is 8 + Jack's Dexterity + Jack's proficiency modifier) or they take double damage from the attack.
And yes, the Sneak Attack is at 9d6.
At level eighteen Jack is at Rogue (18) and gains the ability to be Elusive. No attack roll can have advantage on him when he isn't incapacitated.
Nineteenth level Rogue (19) gets the final Ability Score Improvement or Feat. Piercer, again from Tasha's Cauldron of Everything, does exactly what Slasher does, just with Piercing weapons. So bump your Dexterity up by 1, you should be nearing the cap by now if not are already there. Also, instead of imposing disadvantage on your opponents' attack rolls, you roll an additional damage die for piercing damage on a successful hit and crit.
Our capstone is Rogue (20) and Jack has gotten a Stroke of Luck. He can turn a miss into a hit or a failed ability check into a success once per long short or long rest.
With all that settled, let's have a look at how good this build is!
Pros:
- You are a damage nightmare. Anyone who gets surprised by you is going to be in for a world of hurt between your ability to not only do heavy damage, but to turn any potential failure into an automatic success so that that first strike is all you'll need. With a finesse weapon in your hand, you'll be an outright terror to almost anyone you turn it on to. Best of all, your opponents can't surprise you... or at least not to the point of being able to get advantage on you.
- You are a fantastic skill monkey. With eight skills and Expertise in all but two of them as well as being unable to roll lower than a 10 on any of them means that you'll have quite a bit of use in a variety of situations... although most all of them will likely lead to someone getting stabbed. It's kind of your thing. Then again, having some quick and dirty healing certainly won't hurt your case with your party.
- You have proficiency in Dexterity and Wisdom saving throws, the two most called for Saving Throws in the entire game. On top of that, should those fail you, Stroke of Luck can give you an auto win when you might need it the most.
Cons:
- You only get one use of Stroke of Luck and when it's gone, it's gone (until a short or long rest).
- Low strength means the few opponents that do find you will be able to toss you around pretty handily as opposed to your nightmarish Dexterity and Wisdom saving throws by the end of the build.
- ...honestly, that's kind of it. Rogues, like Clerics, are broken as hell. Basically, you not getting a magical attack from the class naturally is kind of a bummer and it's really not that much of a bummer given the absolute Holocaust your crits can unleash.
You're Jack the Ripper. Send Scotland Yard half a liver and taunt them as you laugh and make your way out of their sight and into the pages of history after murdering those prostitutes. Just make sure to watch your back, or you might find yourself taunting your opponents From Hell!
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