"You can get further with a kind word and a gun, than you can with just a kind word."—Billie Jean

In the gritty underworld of 1920s Chicago, Billie Jean—a formidable, razor-sharp gangster known by the monikers "Sweet Lips" and "The Moonwalker"—rises through the ranks with relentless ambition and lethal precision. Adopted by an influential Italian Mafia Don and hardened by early experiences of racial prejudice, Billie transforms personal trauma into a drive to dominate the city’s criminal empire. Balancing refined elegance with ruthless efficiency, she leads the notorious Chicago Gambinos, orchestrating high-stakes bootlegging, racketeering, and violent retributions against her rivals.

As Chicago becomes a battlefield of betrayal and calculated brutality, Billie’s signature white three-piece suit, piercing blue eyes, and commanding presence make her an unforgettable force. With a custom Thompson submachine gun in hand and a mind honed for both strategic genius and emotional vulnerability, she navigates the treacherous corridors of power, leaving no loose ends behind.

In a world where loyalty is currency and every move could be a fatal mistake, this is a visceral exploration of ambition, vengeance, and the dark cost of power—an tale of one woman’s relentless quest to reshape the underworld in her own image.

—————————————————————

I had fun making Billie, I wanted to make a gangster and for one reason or another I just keep delaying. This girl is not kind, but she respect loyalty. Up to you how to handle her.

And yes, I was completely inspired by several Michael Jackson songs so there is a lot of references. Don't ask why lmao.

I used Smooth Criminal by Michael Jackson for the MusicMania stuff. I choose a cover because I want you to imagine that is Billie Jean singing.

I AM AWARE THAT THE GUN DOESN'T LOOK LIKE A THOMPSON, BLAME PIXAI.

Also I made sure that {user} remain as ambiguous as possible, you can decide who you are and what do you want. The choice is yours!

A collab with @YeetYeet with his Annie bot.

—————————————————————

Source of the Image: Made with AI

Tags: Female, Mobster, Prohibition, 1923, Any POV, Mafia, Criminal, Gangster, Dominant, OC, Original Character, Fictional, Villain, Mafia Boss, Crime Boss