Absolutely. It plays better with someone familiar with the rules and how the game builds and resolves. A group of novice role-players and without anyone familiar with Fiasco I can completely understand how it would be difficult to get into it.

At a high level, the game starts with everyone at the table defining their relationships to the people next to them at the table. These relationships vary depending on the scenario and can range anything from "siblings ever at war" to "blackmailer and victim" to "celebrity and spurned fan". Every scenario has dozens of combinations to ensure hijinks ensue.

After that, each player determines their characters "needs". This is their characters primary motivation for the session. These range from things like "to get out of your dead end life" to "to get free of the person they want you to be" to "to get even without getting taken down yourself".

After you know your relationships and your needs, you need to fill in the blanks between the two. If you "need to get even", and you have "a sibling rivalry", it makes sense to setup a backstory about the time your sibling showed you up or embarrassed you that you want to resolve. These blanks aren't revealed during character creation, but during the role-playing portion of the game.

There are also "objects" which are introduced during character creation. These are items which feature a prominent role during the game. For example, one item might be a "bag of drugs" or a "key to the vault" or a "pearl gripped revolver". The actual meaning of these objects is completely up in the air, but more often than not with the combination of character and relationship a story starts to form about the objects that are important.

The last thing to consider during character creation are relevant locations. Like everything else, these aren't meant to railroad you down a path so much as give you an idea of what areas are important during the game. Think of campy movies as inspiration here. Important stuff happens "inside a bathroom with a line forming outside" or "the outhouse at the camp" or "inside the illegal gambling den". How and when these locations come up is not defined, but up to the players.

At the end of character creation, everyone has a basic idea of their relationships to the people next to them as well as objects or locations which are relevant to them. It's time to start filling in the blanks by proposing a scene in which you lay out the setting (maybe one from character creation) along with the characters involved (based off of relationships or discovered connections) along with your goal for the scene. If you're brothers who have a long time sibling rivalry, maybe your goal for the scene is to finally confront you brother and expose all the times they chose the fame and spotlight over friends and family which are "what really matters". It's completely up in the air at this point with the relationships and motivations you uncovered earlier acting as guiding posts for directions the game can take.

The challenge here is you need a collaborative role playing group as you're looking to reach an ending which everyone is satisfied with. Sometimes that means leaning into the villain role and understanding what happens to the villain in the type of story you're putting together. Sometimes that means leaning into the tragedy which stories sometimes become. Sometimes it means you're the big damn hero that prevailed against all odds at the cost of everything dear to you. The point is, by the time story telling starts everyone plays an equal role in determining the outcome of the story and the main objective is to tell a good story not to be the "winner".

I find Fiasco works extremely well with settings like the Coen brothers movies. Think about Fargo. It has a ton of interesting characters, none of them wholly good, but all of them compelling and connected to each other in unexpected ways. As long as you're able to roll with the punches and make a compelling story out of things, Fiasco is one of the most rewarding systems out there. But you're setting your own pace and your own challenges, so someone expecting a structured adventure like you'd get from an experienced DM with a known setting is going to be disappointed. Telling the story is up to EVERYONE, not just one person laying out the rules.