SPLITTING IMAGE: Luckiest X-Man Alive, longshot

Table of Contents

Character | Build Goals | Level Builds | Playstyle


I’m a huge fan of Ann Nocenti’s work. She’s a master of the unpredictable. When her name is on the byline the only thing to expect is the unexpected. She put Matt Murdock on a subway literally to hell for some devil vs. devil action against Mephisto. She created—for me—Daredevil’s most compelling rogue, Typhoid Mary, whose backstory includes personality disorder and a whole lot of trauma. Unfortunately, this was the 80s and comics weren’t really known for nuance back then. Which is to say, Ann is usually ahead of her time. That brings us to Longshot.

Longshot is both ahead of his time and also stepped in the 1980’s lack of nuance. On one hand, he is a cloned product used to fight and kill for TV ratings. He’s a reality TV rockstar, created by the worst-possible amalgamation of the USA’s corporate greed and teeth-gnashing sensationalism. He’s a perfect encapsulation of modern pop culture and current events. Even his challenging the societal bonds placed on him, and fighting back seems all too emblematic.

Unfortunately, he was designed with the “glitz and glam” of the 80s. He’s soaked in black leather like an 80s rock star, he’s got a distinct hair-band mullet, a pearly white smile, and an eye that glows making it look like his face is locked in a perpetual wink. Oh, and he has a throwing knife bandolier, as if to one-up Crocodile Dundee’s “that’s not a knife.”

Anyway, I’ve always adored Longshot. The hollow bones, the cool jacket, the knives, the warwolves— a story for another time—and especially the luck powers. On the list of cool super powers, luck doesn’t make the list. It seems so banal, mundane. Then you see it in action. Everything goes his way. He even married Dazzler. Probability, physics, reality, all warp to his advantage. Now you’ve got yourself a compelling D&D build.

When we talking about doing a Luck + Fortune themed month for BLACKPUDDING, I knew I had to build D&D’s luckiest X-Man, Longshot!

Build Goals

  1. Longshot must have vast probability altering abilities resulting in an absurd amount of luck both offensively and defensively.
  2. He must also be deadly with daggers, and other thrown weapons. This should aim to include improved criticals.
  3. Longshot has access to a minor regenerative factor.
  4. He can also read memory imprints, and has some supernatural charm abilities.
  5. He must be fleet of foot and agile given his supernatural lightness.

Level Builds

Level one

Was there any doubt this was going to be Halfling? Their access to the Lucky racial trait and subsequent luck-based feats combined with devil-may-care bravery and nimbleness are quintessential Longshot traits. Sure, Longshot isn’t short (he’s supposedly 6’2″) but he does have hollow bones which means he only weighs 80lbs. That is definitely a suitable build to classify as a small creature.

For a subrace, Longshot could have been nearly any of them, but, Ghostwise was the most appealing as to give him some minor psychic communication abilities to hit one of our build goals early.

In full, Longshot gains the following abilities:

  • Lucky (feature): If Longshot critically fails on attack rolls, ability checks, or saving throws, he may re-roll.
  • Brave (feature): Advantage against the effects of being frightened.
  • Halfling Nimbleness (feature): He can move through any space occupied by a creature larger than him. This is the most naturally Longshot ability other than pure luck.
  • Silent Speech (feature): Longshot can communicate telepathically with any creature with 30 feet as long as they speak the same language.
  • He also receives a +2 bonus to Dexterity, and a +1 to Wisdom.

With racial traits alone, Longshot is well on his way to completing several build goals. How lucky for him.


For Longshot’s build, we’re going to start with the Fighter class. We definitely plan to multiclass, and with that in mind, a first-level dip into Fighter is always a solid place to go. Doing so at level one gives this build several key elements of our build goals.

Perhaps the most important is taking the Thrown Weapon fighting style. This is a new optional class feature from Tasha’s Cauldron of Everything, and helps us build the perfect Longshot. Nothing says “The Mullet from Mojoworld” quite like his bandolier full of throwing knives.

What this fighting style does, is allow Longshot to draw a dagger from his bandolier with the same action he uses to attack with it. Additionally, if the attack hits, it receives an extra +2 on the damage roll. For a standard d4 dagger, this puts the average damage at four, which makes it statistically more deadly than any d6 weapon when thrown.

First-level fighters also get Second Wind which allows Longshot to regain hit points equal to 10 + fighter level on a bonus action once per rest. This satisfies his character trait of having limited regenerative health.

Ability scores

To keep it consistent, for Longshot’s ability scores, we used the standard array.

Dexterity (15) +2
Constitution (14)
Charisma (13)
Wisdom (12) +1
Strength (10)
Intelligence (8)



For Longshot’s background, he gooes custom with Mojoworld Freedom Fighter. As a background feature, he took Far Traveler, which marks his mannerisms and behaviors as odd carryover from Mojoworld. His suggested characteristics are borrowed from Soldier, as he was born and bred to fight for entertainment before becoming a freedom fighter. This custom background gives him proficiencies in Sleight of Hand and Survival, as well as with a dice set and the Sylvan language which is our stand in for the language of Mojoworld.


This build is the first one—for BLACKPUDDING—where starting equipment is such a mismatch for the build that we’re actually gonna take the gold. it only seemed fit to leave this up to the dice, and see what luck had in store. After rolling, Longshot managed to secure a bag worth 90gp, which is more than enough.

With the gold, the following items were purchased:

  • Leather armor
  • 25 daggers (Give us a throwing knife bandolier and we’re gonna fill it!)
  • 3 spears (bigger enemies need bigger damage)
  • Burglar’s pack (essentials of a revolution)
  • 1 Dice Set (When you’re this lucky, gambling comes easy)
  • 10 Darts (Backups for the backups)


Levels two, Three, and Four

At second level, Longshot stick with Fighter to pick up Action Surge which will allow him to take one additional action on a single turn per short rest. Why throw one dagger when you can throw two?

With third level, Lonshot continues down the fighter path, picking up his Martial Archetype. For him, Champion makes the most sense. While Shatterstar might have a legitimate claim to Mojoworld’s most deadly product, Longshot’s not far behind.

More importantly is his access to Improved Critical. Now Longshot scores critical damage on a 19 or 20 on the attack roll. For a character that will built entirely upon maintaining advantage and re-rolling dice, doubling his chances to critical is stacking the deck.

Hitting fourth level gives Longshot an ability score improvement, and the chance to take a feat. As there are several luck-based feats available, the goal is to take as many as possible.

Second Chance is the one to take here. Not only will it let Longshot force an attacker to reroll its attack, hoping for a miss, but it gives +1 to Dexterity which takes him to 18 overall with a +4 modifier on all thrown attacks.

Level five

Getting the all-important ability score improvement allows Longshot to jump into another class. This is where our man with the mojo picks up his first level of monk. This gives Longshot access to Unarmored Defense equal to 10 + his Dexterity modifier + his Wisdom modifier which equals the same armor class as leather armor, so drop the armor and pick up a radical leather jacket steeped in the 80s aesthetic.

Doffing armor will also give him the ability to use Martial Arts, and use bonus actions to strike with an unarmed attack once per attack. These bonus attacks can use Longshot’s newly acquired martial dice.

Action economy is going to be something to keep an eye on with this build. After level five Longshot can attack once, with a bonus unarmed strike.

What this breaks down to is 1d4+6 + 1d4+4 damage per attack action, for an average of 14. With an Action Surge that goes up to 25 without even using Improved Critical.

Levels six and Seven

Reaching level six, Longshot stays with monk and unlocks the following abilities as part of unearthing his inner Ki (see, luck):

  • Flurry of Blows: After taking the attack action, Longshot can take two unarmed strikes as a bonus action.
  • Patient Defense: Longshot can take the dodge action as a bonus action.
  • Step of the Wind: He can Dash or Disengage as a bonus action and his jumping distance is doubled.

Lastly, Longshot’s movement speed increases ten feet to 35 feet in total. Talking Halfling made sense to get Longshot access to his trademark wellspring on luck, but it left his fleetness of foot lacking. This addresses that.

Level seven brings another level in monk, and a monastic tradition. As his tradition, Longshot takes Drunken Master. No, he’s not a lush, but I wanted to ensure that his luck was efficient and dumb, affecting both his combat prowess and defensive happenstance. Drunken Master is perfect that.

The most important feature of this level is “Drunken Technique” which allows to Disengage as a free action after Longshot uses Flurry of Blows during which his movement speed increases by another ten feet. The value in this is that he can go blow for blow with an enemy up close, and then slide 45 feet away without taking an attack of opportunity and be in position to rely on his throwing knives again.

Lastly, Dazzler’s husband is so lucky he can now deflect missiles, deadening their damage and tossing them back at enemies. A friendly reminder that with his thrown weapon fighting style, were he to do so, it would be a +2 to the resulting damage.

Levels eight and Nine

At level eight Longshot reaches his fourth level of monk. Here he gets access to Slow Fall, which means that he’s so lucky that falling from deadly heights means nothing the hollow-boned wonder.

Tasha’s Cauldron also provided the optional Ki ability to let monks gain healing equal to a martial arts dice roll plus proficiency. This gives Longshot another option for regenerating health.

He also gets another ability score improvement which he’ll spend another luck-based feat available only to halflings, Bountiful Luck. Essentially, this allows Longshot to share his Lucky feat (advantage) with anyone within 30ft of him, as a reaction.

Note: If you plan to use this build, please clear it with your DM first. Bountiful Luck is often considered a busted ability, and it can cause a great many headaches. Your DM may not be so receptive.

For our thoughts on the luck-based feats, check our article: xxxxxx

Level nine sees a return to the fighter class and the Extra attack ability. This allows Longshot to attack twice, each with a bonus attack as granted by monk. Without Improved Critical or Flurry of Blows, that’s an average of 56 damage while using Action Surge.

Level Ten

Level ten brings with it another multi-class detour, this time into rogue. The idea of “luck” as it relates to Longshot is all-encompassing. He’s not just absurdly lucky in the way that every probability bends to his will. He’s also just naturally good at everything, and if something somehow doesn’t go his way, it’s then that he exerts his control on chance.

Few classes are as naturally skilled as rogues. Whether it’s springing a trap unharmed, surprising an enemy with a deadly blow, or passing through a security checkpoint with but a wink of their eye, those are rogue trademarks. They’re also Longshot trademarks.

At first-level rogue, Longshot gets the following features:

  • An additional skill proficiency (Sleight of Hand)
  • Two skills expertise (Acrobatics and Survival)
  • Sneak Attack: An extra d6 damage on an any attack on enemy you have advantage against, or is within five feet of one of its enemies.

Note: While all luck-based feats mechanically give advantage, rules as written they are different. It’s the understanding of this build that using Longshot’s Lucky racial trait does not trigger Sneak Attack damage, but consult with your DM to see if they differ.

With the added d6 of Sneak Attack damage, Longshot’s two attacks, can now average 62 damage per round with an Action Surge. If we add in Flurry of Blows, that’s improved by another twelve to hit 74. Without an Action Surge, but just one critical on our three dice rolls, the average damage is 45. Getting just one more critical out of six rolls of course pushes that to 90 damage on an Action Surge.

Levels eleven and twelve

Second-level rogues gain access to Cunning Action which allows them to Dash, Disengage, or Hide as a bonus action. Now, this might seem redundant with some of the Monk abilities Longshot has, but if he doesn’t need to burn his luck on any of these Rogue Cunning Actions, he can save them for deflecting missiles, or more importantly, Flurry of Blows, maximizing damage output. As a Drunken Master monk, he can also freely disengage after using Flurry of Blows as well.

Third-level rogues can select a Roguish Archetype and Longshot is taking the new Soulknife archetype.

At third level, this will allow him to wrap his mastery of probability around a skill check adding an extra d6 to the roll. He can also choose to concentrate his latent psychic and luck abilities into a single throwing knife attack using Psychic Blades. If he does so, the damage of that attack is rolled with a d6 and the damage type is psychic. He can also follow up with a bonus attack using a d4 psychic damage.

One very important thing to note about third-level rogues is thanks again to Tasha’s, as a bonus action they can choose to give themselves advantage on an attack by sacrificing all movement on that turn. What that means, however, is that the next attack will automatically provide Sneak Attack damage (now 2d6) on a hit, and Longshot doesn’t miss.

Levels thirteen and fourteen

Now we arrive at lucky number thirteen. It just so happens, that for Longshot, it’s predictably lucky. Fourth-level rogues get an ability score improvement, and while there are so many things we probably should give Longshot, we’re doubling down on luck by taking the Lucky feat. This gives Longshot three additional “luck points’ per long rest that he can spend to gain mechanical advantage on any attack roll, skill check, or saving throw. He can also impose mechanical disadvantage on any attack made against him.

Level fourteen brings our final level of Rogue, and the ability to Uncanny Dodge. Should an attack weave itself through Longshot’s probability tinkering, it doesn’t matter. He’s still got luck on his side, and can use his reaction to half the damage.

Levels fifteen and sixteen

This is the home stretch, and we’re going to take fighter all the way home. Sixth-level fighters get an ability score improvement, and unlucky for us, there are no more luck-based feats to take. However, there is the Sharpshooter feat which allows Longshot to ignore disadvantage imposed by long-ranged attacks. He can also ignore half and three-quarters cover as well as take a penalty the attack roll to do massive damage. With the amount of options he has to buff his attack rolls and give advantage, the idea of taking a -5 from his +9 in order to up the damage by +10 seems like a very advantageous gamble.

With his next level of fighter, Longshot can bend his luck to add half his proficiency bonus to any saving throw he isn’t already proficient in. Those include Dexterity, Intelligence, Wisdom, and Charisma.

Levels seventeen+

Eighth-level fighters again get an ability score improvement, and this time it makes the most sense to sink the +2 into Dexterity to max it out. This will improve his attack rolls, armor class, and Initiative.

Ninth-level fighters get the Indomitable ability to reroll a saving throw they fail once per long rest. Oh, if you thought Longshot was done finding ways to gain advantage on a roll…

Tenth-level fighters get an additional fighting style. There aren’t a ton of options that help expand on Longshot’s strengths unfortunately, however, Superior Technique allows him to draft maneuvers from the Battlemaster which offers a whole slew of clever techniques on which to hook his endless luck.

The crowning achievement of this build is the eleventh-level fighter, and yet another additional attack, making it three per round without Action Surge.


The cornerstone of this build is having access to as much chance to gain advantage as possible. Being a Halfling gets Longshot access to all of the luck-based feats and abilities (Lucky trait, Lucky Feat, Bountiful Luck, and Second Chance) which gives him several to gain advantage or impose disadvantage.

As further representation of his luck, it was important to improve his chances to score criticals. The Champion subclass delivers this, having three times the chances to score critical. Additionally, access to Rogue allows Longshot to guarantee a critical with punishing damage in some instances.

Sharpshooter and high attack roll modifiers increase his ability to hit with thrown weapons (his weapon of choice), and exert more damage. Soulknife synergizes with this benefit, allowing him to change the damage output to psychic.

As in the name, it also needed to be a long shot for him to be hit in return. Drunken Master, Cunning Action, and Uncanny Dodge all give him a multitude of ways to avoid being hit, and slipping back out to comfortable attacking range. Which is good, because Longshot’s armor class tops out at 16. His defensive focus is to rely on slipperiness and advantage before armor. It’s very effective but non-traditional.

Lastly, despite fairly pedestrian ability scores, Longshot’s luck makes him fairly skilled at most things with Intellect skills being the only source of concern. Fortunately, he can use his psychic dice to empower his skill use, which is really the only purpose they serve.

Which brings me to the meta of a luck and fortune-based hero having so many dice to roll. It’s thematically very cool. That said, playing this build can be a bit like playing a free-to-play mobile game. There’s so many different dice and skill pools here, and it’s hard to understand how best to use them. Superiority dice, martial arts dice, psychic dice, sneak attack dice, maneuvers, Ki, Luck points, it’s a feature-rich build, and that can be daunting.

However, if you love to roll dice (including the same ones over again), score criticals, and generally be a nuisance to your DMs best laid plans, this is the build for you. For real, though, run this one by your DM before giving it a shot.

Leave a Reply