Daring Flynn Rider from Disney's Tangled is a self-described swashbuckling rogue, which makes him a great fit for a Dungeons & Dragons campaign. As Tangled: The Series reveals, Flynn (a.k.a. Eugene Fitzherbert, a.k.a. Horace as he was originally named) was orphaned as a child when his father, King Edmund, ordered everyone to evacuate his kingdom and a servant took infant Flynn to an orphanage. Flynn never learned any of this and believed his parents were fearless adventurers, not royalty.
When Flynn Rider meets Rapunzel, he says he grew up reading stories of Flynnigan Rider. He dreamed of becoming a man who went on thrilling adventures and lived an audacious lifestyle. In Tangled, Eugene renames himself after the character and becomes a successful thief, living up to his childhood goals. With a silver tongue, expert dueling skills and a set of sticky fingers, many players may want to recreate the him to go on adventures of their own.
The Best Race for Flynn Rider
Flynn is, of course, human, so the best race to go with in D&D Fifth Edition is Variant Human. This allows the player to start with additional skills, ability scores improvements and a feat. The two +1 bonuses to ability scores should go to Dexterity and Charisma. Additionally, the additional language choice Variant Humans get fits with Flynn's history of traveling across the seas while building his career as a thief. Players could choose one that will be particularly helpful during their campaign, such as Elvish.
When it comes to skills, Athletics and Acrobatics are fantastic options that Flynn will certainly use as a Rogue. He's also so good at staying on his feet that it seems he's always catching a lucky break -- something players should convey by choosing the Lucky feat. This enhances his ability to escape capture and land those impressive and unlikely maneuvers by giving him three Luck Points per long rest he can use to roll an additional d20. This roll can be used to for an ability check, saving throw or attack. It can also help cause an attack roll made against the player to fail.
The Best Class for Flynn Rider
It's no surprise that the perfect class for Flynn is Rogue, but the tricky part is choosing his subclass. While Thief makes a lot of sense and grants players a climbing speed that fits Flynn's skills, Swashbuckler works a bit better based on his charming nature. Introduced in Xanathar's Guide to Everything, Swashbuckler grants Flynn several key moves that reflect his skills in battle. Fancy Footwork will get him out of opportunity attacks, and Rakish Audacity gives him his Sneak Attack bonus when he's going one-on-one with an opponent. This also allows him to add his Charisma modifier to his initiative.
At later levels, that Flynn Rider charm truly comes into play. With Panache, he'll be able to charm a non-hostile creature or cause one that is aggressive to have disadvantage on attacks against the rest of the party. When he's reached his subclass' capstone, Master Duelist, Flynn will fully realize his dueling skills and be ready to sword fight with more than just Maximus.
Flynn Rider's Ability Scores & Skill Proficiencies
Whichever subclass is chosen, prioritize Flynn's Dexterity, then focus on Charisma. Dexterity will ensure that Flynn can get the drop on enemies during combat since Rogues use their DEX mod to hit and it boosts Stealth and Sleight of Hand checks. Plus, having a higher DEX will improve his Armor Class. A higher Charisma score will make him more persuasive and deceptive, and it will boost his initiative bonus if playing a Swashbuckler. Flynn is also naturally charming, so the stat reflects that aspect of his character.
Where to put the rest of the remaining scores is mostly up to the player. However, it is wise to increase his Strength for climbing checks and to keep his Wisdom and Intelligence from receiving negative modifiers.
The Best Background for Flynn Rider
The Criminal/Spy background suits Flynn well. With this, he can gain proficiency in water vehicles, which makes perfect sense for someone who traveled from port to port. It also grants another skill proficiency. Insight is an excellent choice because Flynn seems able to read people and use it to his advantage, such as when he quickly realizes that he can try and convince Rapunzel that leaving the tower would crush her mother's soul.
Pirate is another suitable option that provides a similar feel. This comes with the Bad Reputation feature, which fits for someone who famously has a wanted poster. It would also give him another opportunity to snag proficiency in Athletics and Perception.
The Best D&D Feats for Flynn Rider
In addition to Lucky, there are other feats Flynn should try to pick up later in the game. Mounted Combatant serves his character well, as Flynn is a skilled horseman (as long as the horse isn't Max). The feat gives him several advantages when riding a horse, most importantly the ability to use his Sneak Attack while mounted. There is also Athlete, which provides a different way to improve climbing and jumping. It gives a Strength or Dexterity boost, allows him to stand up from prone for less movement, and makes his jumps more effective.
Flynn would also benefit from Mobile to reflect his agility on difficult terrain. Tavern Brawler is also perfectly suited for Flynn Rider, who frequents the Snuggly Duckling and is skilled with a frying pan. The feat gives him proficiency with improvised weapons and improve his hand-to-hand combat skills. Plus, it boosts Strength or Constitution, which can make up for a lower ability score. Fighting Initiate is also a solid choice, granting him a Fighting Style, such as Dueling.
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