Help building a character that fits this desperado/once upon a time in Mexico like description

[Illyunkas De’lorinth]

I’m playing 5e dungeons and dragons. My character is starting at level 4 and I want to build a character influenced by the main character to the movies desperado and once upon a time in Mexico. I’ve narrowed the possible races down to half elf, human, and Tabaxi since the Tabaxi are from a place influenced by Mexico, central, and South America. I think I’d prefer half elf though because I’m a little tired of playing Tabaxi characters. The characters backstory is that he was once a member of a traveling group of musicians that secretly assassinated and spies on the people they were entertaining. Although money was the main factor my specific character took more of a political interest and never took jobs that could potentially influence politics in a way that he disagreed with. Eventually he settled down, got married, and had children, but it was in his nature to still perform and to still travel so occasionally he took jobs to settle his restlessness. One day a skeleton in his closet emerged in the form of a revenge hungry politician that was appearantly not actually assassinated. The politician forced him to watch as his family was tortured to death. With his spirit broken he received the worst punishment of all. He was allowed to live knowing that his own actions brought this upon his family. Now he has decided to finish the job and actually assassinate the politician, but he needs to develope a plan first. In the meantime he is adventuring in hopes of gathering allies willing to help. My dm has said he will definitely give me a shot to get my revenge in between adventures, and any of my group that wants to help can tag along. He also said he will plan for it to be a decent sized group so if no one wants to help I may end up going on a suicide mission which I’m ok with. Obviously I should take bard, but I don’t know what college to take or if there are any specific options, MC, feats, specific spells, or otherwise, that would help build upon my characters concept. Possible flaws are that I’m headstrong and never back down or that I have a soft spot for protecting the innocent often putting myself into great danger. Obviously this isn’t exactly the character or the story from the movies, but it’s inspired by them. If you want more details please feel free to ask and I will answer. Thanks.

 

[Leatherhead]

College of Whispers was made for Bard-Assassins.
For any half-elf, the Elven Accuracy feat is great.
As always, dipping levels of warlock increases your kill-power significantly. Hexblade is the current flavor, and synergizes well enough with any melee-focused charisma based character. Additionally, swearing a blood-oath to something so that you can get revenge would be easy to fit into your character.

 

[Illyunkas De’lorinth]

Could you go more in-depth about hex blade? I’m curious about mixing warlock with anything because they seem pretty bad ass.

 

[Leatherhead]

The general idea is that you want to get 2-5 levels of Warlock, pact of the blade. Yes, the other pacts are better in general, but in your case blade pact is going to help your theme.

2 Levels gives you highly desired Devil's Sight and Agonizing blast combination. Hexblades in particular you get Hex Warrior for way better armor, and the ability to attack with CHA instead of dex. Hexblade's curse is kind of nice against hard targets, as it gives bonus damage and extra crits. This is basic level stuff though.

5 levels gives you access to Thirsting Blade, And you can really start crit fishing at that point. Using darkness to get advantage, your curse, and making two attacks per round, you crit on 19's or 20's. When you land a crit: Use your Psychic Blades Bard power to pile up the damage, just like a Paladin or a Rogue.

 

[Illyunkas De’lorinth]

Thanks. That definitely sounds like a play style I’d enjoy.